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How to Recognize the Hidden Signs of Burnout with Leah Weiss

June 13, 2025 Leave a Comment

How to Recognize the Hidden Signs of Burnout
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In this episode, Leah Weiss discuss how to recognize the hidden signs of burnout. She shares how burnout can creep in under the guise of purpose, why discernment can’t be done alone, and how to find your way back to yourself.

Key Takeaways:

  • The issue of burnout, particularly in the workplace.
  • Personal experiences and challenges related to burnout.
  • The importance of recognizing signs and symptoms of burnout.
  • The concept of discernment in addressing dissatisfaction.
  • Distinction between burnout and compassion fatigue.
  • The role of community and support in navigating burnout.
  • Factors contributing to burnout at individual, team, and organizational levels.
  • The significance of psychological safety and team dynamics.
  • The search for meaning and alignment of personal values in work.
  • The impact of entrepreneurship on well-being, particularly for women founders.

Leah Weiss, Ph.D. is a researcher, lecturer, consultant, entrepreneur, and author. She teaches Compassionate Leadership at the Stanford Graduate School of Business, where she created the perennially-waitlisted course “Leading with Mindfulness and Compassion.” She is Founding Faculty at Compassion Institute. She is also the co-founder of Skylyte – a company that specializes in using the latest neuroscience and behavior change to empower high-performing leaders and managers prevent burnout for themselves and their teams. Her first book, “How We Work: Live Your Purpose, Reclaim Your Sanity, and Embrace the Daily Grind” focuses on developing compassionate and soft skill-based leadership while also offering research-backed actionable steps towards finding purpose at work.

Leah Weiss:  Website | Instagram | LinkedIn

If you enjoyed this conversation with Leah Weiss, check out these other episodes:

Embracing Emotions at Work with Liz Fosslien

How to Deal with Burnout Through Self-Compassion with Kristin Neff


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Episode Transcript:

Eric Zimmer 00:01:04  What if the very thing that gives your life meaning is also what’s burning you out? That’s the paradox. Leah Weiss found herself in teaching compassionate leadership at Stanford.

Eric Zimmer 00:01:16  Working with organizations inspired by the Dalai Lama. Doing the kind of work most of us dream of. And yet she was falling apart. In today’s conversation, we unpacked the silent erosion of self that can happen even when everything looks right on the outside. Leah shares how burnout crept in under the guise of purpose, why discernment can’t be done alone, and how the small act of knitting helped her find her way back to herself. This episode is a map for anyone wondering is it me? Is it the job or is it the world we’re trying to survive in? I’m Eric Zimmer and this is the one you feed. Hi, Leah, welcome to the show.

Leah Weiss 00:01:56  Thanks for having me. It’s great to be here.

Eric Zimmer 00:01:59  Yeah, I am happy to have you on. As we were talking before this interview. You were on the show almost four years ago to the day. It was just kind of interesting that we talked at this time and amazing that it’s been four years. So I’m really happy to have you back on.

Leah Weiss 00:02:15  I’m really happy to be here and continue this conversation. We started many moons ago in a very different climate that we’re in today.

Eric Zimmer 00:02:24  Yeah. And our basic topic is going to be oriented around the idea of burnout, you know, workplace burnout primarily, but we know it extends well beyond the workplace. But before we get into that, let’s start like we always do with the parable. There’s a grandparent who’s talking with their grandchild, and they say in life, there are two wolves inside of us that are always at battle. One is a good wolf, which represents things like kindness and bravery and love, and the other is a bad wolf, which represents things like greed and hatred and fear. And the grandchild stops and thinks about it second and looks up at their grandparent and says, well, which one wins? And the grandparent says, the one you feed. So I’d love to start off by asking you what that parable means to you in your life and in the work that you do.

Leah Weiss 00:03:10  I think in terms of how I hear that in my life, one of the ways that this really resonates with me is acknowledging the degree to which we’re influenced and shaped by our surroundings, and that we want to be thoughtful about that.

Leah Weiss 00:03:27  I’m a parent of three young children, and so we talk a lot about the navigation of being a friend to people who need support, who are in distress, but also understanding what you need to thrive so you can be that friend. And I think one nuance I would say when I read this parable again in advance of our conversation is it really caught me these words good and bad, AD, because I think the way that I tend to think about this is tendencies that pull us in directions that are connective, supportive, conducive of compassion or fear based scarcity. And I don’t know that labeling them as good or bad helps us in actually navigating these currents that we all have. So it’d be interesting to talk that through. And then for the other side that you asked about in my work, how does this influence how does this relate? I think I spend my time now working within companies, helping to set up teams, climates of courts in the storm, within organizations that are navigating a lot of change and even often toxicity.

Leah Weiss 00:04:47  How do you think about feeding the positive? Not just within yourself, but collectively? So I think that it really does come to the heart of what do you do when you’re navigating things that are problematic, and how do you create mutual support so everyone can move towards the proverbial best selves, healthiest selves, together?

Eric Zimmer 00:05:08  Yeah, I think that idea of good and bad is really interesting. It’s brought up a lot, and I’ve said a lot of times on this show. You know, I’ve always loved the Buddhist phrasing of these things as skillful and unskillful actions. Like, I feel like that speaks to, you know, what we’re really saying more, but it’s kind of a boring story. The grandparents said there’s this unskillful wolf, and he was sent away to corporate training. And, you know, so I thought where we might start is with you and burnout because I think you suffered. I don’t know if this is how you would say it, but you certainly had a case of it. And I’m wondering if you could kind of share what that was like, what happened, and, you know, sort of how you made your way out of it. And I think that’ll lead us then into talking about this more generally.

Leah Weiss 00:05:56  Yeah, absolutely. I’m happy to share. I think, you know, for me, what is so interesting, at least from the vantage point of today, is to uncouple kind of what happened externally and internally. For me, that led me to kind of realize at some point a few years ago that I just I don’t want to go on this way. This isn’t how I want to work, how I want to parent, how I want to be in the world. I had just turned 40 when we spoke last time. I think for me, that was actually, you know, some of these symbolic ages I feel like really helped us ask the questions around, am I where I’m supposed to be in my life? And for me, I think what I was seeing was I was working in a way that was not sustainable, that I was missing elements of my children’s life because I was traveling or preoccupied when I was there.

Leah Weiss 00:06:56  I think a lot of what I was hooked by to use another kind of Buddhist psychology term. When I went back to Stanford to work full time after graduate school. Each of us kind of has currencies that we buy into. And for me, this kind of academic research understanding, kind of contributing in that space was so exciting. But also it led me to work around the clock, let go of a lot of what I now know are the signs of burnout. You know, tipping from starting to let self-care go, displaced frustration from work and to other elements of life. And then, of course, like for me, as someone who identifies as a practitioner, as someone who’s trying to work on myself, like I’m sure everybody listening to this podcast can relate to. Spent many years in doing meditation retreats, cultivating skills that it really hurt to admit weren’t working in this environment, and compounded by, you know, living in Palo Alto, one of the most expensive places in the world. Having three children, being a breadwinner for our family.

Leah Weiss 00:08:14  And I think then for me, what I experienced was a very similar to what a lot of people do. One of my mentors was the one who really made me see where I was at, and that often is the case. It’s hard to self-diagnose when we’re burned out. It’s our loved one’s a close colleague who calls us out and says, you’re not the version of yourself. You know what’s happening. So she called me out as kind of the frog in the pot over time, and I really all of a sudden I remember that breakfast viscerally, where I felt it and I saw it. And then, you know, that’s kind of the first step, but that’s also where the work begins. And one of the things I’ve been really interested in is playing both sides of this equation of when do you make decisions around, I need to change my external circumstances, which like, who in the world isn’t thinking about that now with the great resignation? Right. So when do I decide this fit isn’t working? When do I decide this is me? I can quit, I can move, but this is my stuff that’s going to follow me wherever I go.

Leah Weiss 00:09:18  And how do you uncouple all of this and understand what you need to do? So being a nerd, I’d been working in this space of burnout and compassion fatigue for many years, but I started to take this lens more. Looking at the question around how do you think about culture, of workplaces, of our communities and how I had guided so many other people through this question of, am I in the right career? Am I in the right location? Am I living the life I’m wanting to live, and then asking all those questions of myself and letting myself off the hook for like, I can’t expect myself to meditate my way out of this. And what if I allow myself to also come to a conclusion like this isn’t where I want to raise my kids. This isn’t the work that I want to be doing. This isn’t the way I want to be doing it. And let that part of the equation open up, which I think is interesting to look at now because it’s where so many people are, right? Because we can move now and people are quitting their jobs now and there’s other jobs available or that perception.

Leah Weiss 00:10:24  The set of questions. If you feel like this is not my beautiful life that you’re living right now, how do you start to go through that process in a way where you’re not blowing everything up irretrievably, but kind of in a thoughtful way, asking the right questions in experimenting with steps that you’re not going to completely end up regretting.

Eric Zimmer 00:10:44  Yeah, I think that question is so fundamental to so many things. Is this something that I need to change in the outside world, or is this something I need to change inside myself? Is that a little bit of both? And I think this is why I have often said, I think the Serenity prayer sums up so much of what life is about, right? Should I accept this or change it? And the wisdom to know the difference is really the hard part. What things for you helped you or still help you in sorting that question out? You know, how do you go about when you find yourself at one of those points and you’re looking in those two directions? What are some of the tools or ways, thought processes, whatever, that help you find that wisdom to know the difference?

Leah Weiss 00:11:28  I mean, I think there’s always some element of having quiet, some version of of prayer, juju prayer, in my case, meditation, if you will. Like there’s those elements. But I think what I’ve really been leaning into as well, you know, just getting back to like Embodied elements of life, like cooking with my little kids. Walking a ton. Knitting. I’ve been knitting so much. Gardening, like putting physicality front and center and and slowing down to do that and taking when that feels odd, to move back and forth between the pace of ideas and screens and zoom meetings, you know, hour after after hour. And it does feel jarring to be back into bodies and relationships and listening more deeply. And I think even taking that kind of discomfort of transition as an important daily practice has been huge. And just like so many of us, you know, sleep in the last few years with the pandemic, you know, we were already an insomniac world. But how much more so now? and, you know, experimenting with like what happens when I take screens out of the equation when I go back to paper books, when I draw, even though I’m a terrible artist, but I draw because of the process feeling, you know, grounding all the things we’re baking in the world, all the things that we’re like reclaiming.

I think this physicality is kind of shared. That’s been big, big, big for me too.

Eric Zimmer 00:13:10  Yeah, I think the other idea, it’s in the spiritual direction world, and I was trained as an interfaith spiritual director. The word discernment is used a lot. Right. And that’s what we’re kind of talking about. And I’ve more and more become convinced that discernment kind of has to happen in community. It really works much better when I’m not discerning all by myself. When that discernment is happening, by me processing it with other people, obviously the right people, the right circumstances, but still a really valuable part of the process. I want to go back for a second, though, before we move on to you. You’ve got this role at Stanford. You’ve got children. You’re the breadwinner. Your husband still, I think in school and you are doing work that feels monumentally important to you. You are working on compassion research that is sort of backed by the Dalai Lama, right? Like so I mean, you’ve landed in some ways, like dead set into, like, all right, this is it.

Eric Zimmer 00:14:08  And yet there were still aspects of burnout for you in there. Did that make it harder to figure out because the work did feel so meaningful?

Leah Weiss 00:14:19  Oh you’re good Eric. Yes it did. I think it made it harder to recognize it. Even a culture that is a group that’s come together around a shared value with noble ambitions, can still have toxicity and challenge in how to operate and how to function together. That, you know, since that time now I’m well aware, like even if you look at the research, like toxicity and cultural problems and nonprofits where we’re aligned on purpose, they can be pervasive because there’s a sense of you self-sacrifice and you sublimate the how you’re doing things underneath the importance of the mission. And I think I was personally very predisposed to that. And I think that culturally, that is a big part of the experience. And it’s even more painful, you know, and I see this even I do a lot of work in health care these days with the pandemic, when people who are purpose driven, they’re in a line of work because they want to help others, and then they feel divorced in their how they’re executing that work from their core values.

Leah Weiss 00:15:31  I think there is an extra layer of what we’re calling moral injury that happens and disillusionment. Right? Because, yeah, there’s a lot to say about that. And then I think for me it was a lot of self doubt too, and I felt like I was in layer upon layer of kind of worldviews that didn’t align with me as a mom, a woman. You know, academia is not known for notoriously being friendly to women, nor is Buddhist organizational structures. you know, it’s a lot. But I also want to come back to what you said, I think so profoundly this point about discernment in community. And when I went to Boston College for my graduate degrees, that was something that really jumped out at me. Not that we didn’t have community in the Buddhist world that I was being raised in, but I think the way in which it’s understood is really unique and profound. And I think that was something that gave me kind of strength, that amidst feeling overwhelmed, feeling like I’m in my dream situation and it’s not working, but there was access to some amazing people around me, even swimming in the same culture that was dysfunctional.

Leah Weiss 00:16:49  I remember one of my mentors described being in academia is kind of like being in a mafia oriented place, because you have to, like, hook yourself onto the people with power. But if you start getting powerful enough, then you become a magnet for other people who want your turf. And you know all of that. When I first heard, I was like, this is bananas. And by the end I was like, that’s pretty astute. So anyway, the people who are swimming in this kind of dysfunctional toxicity but have their heads on not necessarily just straight, but they have some practice, their grounding in those people that you can come back to to figure out who am I? What does this mean together? Is everything.

Eric Zimmer 00:17:50  One of the books that I’ve spent the most time with in my entire life is the Dao de Ching. It’s an ancient Chinese manual for living well that somehow also reads like poetry. Here’s an example of one verse that I come back to over and over through the years. If you look to others for happiness, you will never be happy. If your well-being depends on money. You will never be content. That kind of simple truth doesn’t just sound good, it actually changes how you live if you let it. It’s simple, it’s direct, and it hits me harder every year. If you’ve ever been curious about the Dao, or just want some ancient wisdom that actually works in real life, I’ve got something special. I teamed up with Rebind to create an interactive edition of the Dao. I handpicked 40 core verses translated them into plain, relatable language and built them into a guide where you can ask questions and get my take in real time. It’s like having a conversation not just with the Dao, but with me too. You can grab it right now at one you feed store that’s spelled T. That’s one you feed. To. If you’re looking for a little more clarity, calm or direction, I’d love to meet you there.

Eric Zimmer 00:19:10  I want to get to where you are now, and I have some questions about that. But I feel like before we do that, it would be helpful to talk about burnout a little bit more.

What are we talking about? What is it? How do we know when we have it? Like, I mean, I think there’s a lot that we can sort of cover in that area. And then I’d love to talk about how your current experience compares to your old experience and the differences there. So maybe we’ll just start with that very simple question. Like what is burnout?

Leah Weiss 00:19:36  Yeah, burnout is this combination of emotional exhaustion, dehumanization, and a lack of self-efficacy. So those are like the academic words to describe them. And it’s also part of the World Health Organization definition and more plain terms. I think a way to think about it is the emotional exhaustion, that feeling of like at the end of a long day, you just don’t have anything left to give. You can’t hear about another person’s problem. You know, the version of you that wants to show up to others is depleted. The depersonalization goes in both directions. So one of the kind of textbook ways people describe it as like the physician who’s become kind of a cynical, rude, like no grace or tact.

Leah Weiss 00:20:25  They’re just like going to get right to the question without thinking about how does that impact you? So it can be the side of personalizing others, but it can also be de personalizing yourself. And they often happen together. So if I’m treating you from a cynical, kind of dehumanized perspective, I’m probably also thinking of myself in that way and the people I’m surrounding myself with. And then the third part is a lack of self-efficacy. This is, I think, the actually trickiest part for building health out of burnout, because the more burnt out you are, the less you feel like you can shape your environment. So then all the options for where would you change yourself? Change the situation seem impossible because there’s no efficacy. Do you feel like a victim in the world is happening to you as part of the illness itself? Yeah. So you can’t recognize the help that is available to you. So you put those three together. One of the ways I often talk about it that people find helpful is it’s not a binary.

Leah Weiss 00:21:28  You have it or you don’t. It’s a spectrum. And so early burnout often looks very similar to workaholism. Middle burnout is like middle stages when you’re losing your habits of self-care, when you’re snapping at your loved ones at the end of the day, and then later stage burnout. You know, significant behavioral changes, either significant depression or anxiety, loss of hope, complete collapse. There’s physical symptoms that happen along the way. With all of this, when you’re burned out, your amygdala is enlarged. Your like old lizard brain. As people often kind of summarize, the amygdala is bigger in your cognitive resources. Your ability to think and problem solve is smaller. Like literally your brain functionality changes when you’re burned out, which is also really interesting. And then when you think demographically, women, people of color, those of us who don’t have a partner, there’s higher risk. And then in the context of the pandemic, you know, we’ve been seeing mass exodus of women from the workplace. and I’d been really looking into this a lot.

Leah Weiss 00:22:37  And the rates of burnout are much higher, which makes sense given all the contextual factors. Parents are higher than non-parents, women are higher, and so forth. So there’s all these other layers and features of the individual, but also the environment that feed into burnout.

Eric Zimmer 00:22:55  And how do we determine burnout from something like depression or anxiety, particularly if burnout eventually manifests itself in depression and anxiety? Is there any way to sort of tell the two apart, and is it important to tell the two apart, I guess.

Leah Weiss 00:23:11  It’s a great question. I think by the time you’re experiencing the anxiety and depression symptoms of burnout, it would be indicated to get mental health support. You’d be at the upper end of the burnout spectrum. And so you would want to be seeing a professional have the professional do the differential diagnosis between burnout or generalized anxiety or depression. One thing that people say you see in the literature, it’s like, is there a sense of it? It gets more acute in the workplace. Or more acute Sunday night blues.  Or anxiety, you know, so maybe you’re you feel like yourself on your vacations, in the evenings and the weekends, but you see your reactive ness heightened in the workplace. That could be an indicator. But for listeners who are experiencing this kind of depression or anxiety, the upshot is basically you want to talk to a professional anyways and work with them to determine, you know, because it might be that you want to have medication or a certain kind of treatment alongside doing a whole discernment process around your professional context and path.

Eric Zimmer 00:24:25  Yeah. As somebody who has had depression in, you know, different forms for a long time and somebody who may have suffered burnout at different points. The relationship between the two is very difficult to figure out, right? Say like, well, depression often to me looks like what burnout might feel like, which is particularly a lack of enthusiasm of anything that takes energy from me. Right. So it’s like that’s one of its signal things is like, anything that takes energy causes me to be like, no.

Eric Zimmer 00:24:56  Which work gets implicated in, right? Work can be one of those things. I think that question around, you know, how do you respond on off work times is an interesting one. What about compassion fatigue? Because you also say this is not the same thing as compassion fatigue. So I certainly know that is something we’re hearing a lot about. Talk about how burnout and compassion fatigue are different from each other.

Leah Weiss 00:25:19  So the interesting thing with compassion fatigue, and I’m sure you’ve come across this, but I think for listeners, it’s good to kind of lay this out. When you start reading about compassion fatigue, one of the first things that you start humming across is people saying it’s not actually compassion that’s fatigued, it’s empathy. And the reason this is important is basically the neuroscience of understanding how our brains and bodies respond to chronic suffering. We have built into us these. If you remember back to psych 101, the ideas of of mirror neurons and the mother infant mimicry that from the time humans are newborns, they read and mimic the parents facial expressions.

Leah Weiss 00:26:10  So we have wired in these emotional kind of tuning forks. One of the things that has been really interesting with the advances in neuroscience in the last decade is we see that people who are chronically exposed to suffering, if they’re responding from a place of empathy. There’s a tipping point in which, like our brains and bodies, can’t stay empathically attuned. All the time we hit a point of overwhelm and collapse where our compassion then goes away. So that becomes interesting. So let’s say in the beginning, it’s useful if I’m with you, Eric, and you’re talking about a problem that you’re facing. It’s useful that I have this ability to mirror you, to understand and respond. We’re social. We’ve evolved to be like tribal in some way. Mutual support is part of survival. But at some point when it gets Eric times a thousand that I’m surrounded by suffering that I can’t solve, then the pain response in my brain that’s mirroring hits a point where it’s not signaling all the time. It like doesn’t function anymore.

Leah Weiss 00:27:25  When we talk about compassion fatigue, we’re actually talking about empathy fatigue. And then what’s interesting about that is that there’s compassion because it’s different than empathy. There’s a way that we can respond to other people’s suffering that doesn’t get depleted and used up is the thought behind it. And interestingly, this is a thousands of years old intuition from wisdom traditions. Right. Like the idea that you could participate in contemplative support of others emits massive suffering. I mean, there’s so many stories all the way back to wisdom, traditions, canons about people who who did that. So the idea then borrows on what does it mean for us as people to learn to respond with compassion rather than empathy? What is the difference? What is that feel like? How do we train ourselves? How do we train our physicians and health care providers to do that? And then therefore, how do we kind of solve this problem of compassion fatigue. So this is a discourse I’ve been a part of since I was in grad school right after September 11th, studying all the rise of burnout and compassion fatigue in healthcare, in first responders and all of those kind of studies.

Leah Weiss 00:28:43  And I think the implications for us today are fascinating, no matter what our line of work is in the pandemic, all the uncertainty and pain and anxiety that we were all navigating this lens of like hitting a tipping point with that where we can’t engage skillfully anymore. So what does that even mean for me is, you know, a parent navigating schools closed and changes in workplaces and yada yada. So, you know, back to your question of that compared with burnout, the way I would think about it is we need to both from the individual side, train people to understand how to respond with compassion rather than empathy, which in some cases means retooling, taking on, feeling the other person’s pain and having a responsive way of engaging with them. But that has an understanding of a type of boundary in support of both people, the person in pain and the other person. So it doesn’t become dehumanized and cynical, but it has a wisdom of understanding. Me getting overwhelmed by your problem isn’t going to necessarily help you, especially if I’m here to be in a role where you need me to not be crying alongside you about your diagnosis.

Leah Weiss 00:30:08  You need me to hold this space. To be able to be clear.

Eric Zimmer 00:30:13  That’s a really interesting idea there. The empathy versus compassion. And I kind of want to go deep down that hole, but I’m going to resist. But I have one question on it, which is do you find often that people earlier in their career. Start from an empathy perspective. Like that’s what comes most naturally. Then one of two things happens. Either they move into quote unquote empathy fatigue and they become cynical, or they figure out how to do this with compassion, and they move into sort of this wise healer mode. Is that the general path?

Leah Weiss 00:30:45  I think that is a really good way to summarize it. And when you said that, it made me think of I remember when I was in grad school doing my clinical training, I was one of the settings I worked in was a Boston Center for Refugee Health and Human Rights, which is headed by this incredible physician who does work with refugees from around the world. Like, talk about someone being immersed in so many unimaginable kinds of pain and trauma on the daily.

Leah Weiss 00:31:12  And I remember walking out of the hospital with him at the end of one of the days, and I was just kind of asking him how he was or how he felt about his day. He just came back to being so grateful to be here. And what an incredible world. What an incredible opportunity. Like he was, you know, coming from that wise healer perspective. And I was the angsty, you know, clinical training, like, overly empathic to the point where it’s probably annoying to be the recipient of for the folks I was working with at that point. I think that’s right. And I think the other thing that reminds me of from the neuroscience perspective is, you know, one of the studies I often talk about in my keynotes is when we brought a group of meditation experts to Stanford, put them in an fMRI machine, had them do compassion meditation and the reward regions of their brain light up, not the pain empathy regions of the brain light up. And I’ve always said and felt like I would love to do the studies where we do this across traditions, right? Like because every wisdom tradition has some version of compassion, contemplative practice.

Leah Weiss 00:32:21  How interesting to see what that looks like as a way to motivate the rest of us to cultivate.

Eric Zimmer 00:33:19  All right. We’ve talked a little bit about what burnout is. maybe some of what it’s not. Let’s talk about some of its causes. And I know that you sort of delineate causes kind of at three levels. I’ve seen in some of your work, which I think is interesting. There’s an individual level. You talk about a team level and an organizational level. And I suppose if we were to take it one step further, we’d say there are societal components also. But walk us through those. What the causes are, you know, kind of in each of those levels.

Leah Weiss 00:33:49  You know, a metaphor that I find helpful for framing comes from the godmother of burnout research, Doctor Maslany, and she uses a metaphor of if you’re trying to understand burnout, what people typically do is analogous to looking at cucumbers in vinegar barrels and being surprised that they turn into pickles. So it’s nonsensical to just look at the individual level, not meaning that there’s nothing we can do as individuals and there’s not contributors, some of which we can address, some of which are intrinsic to who we are.

Leah Weiss 00:34:25  Our demographics. You know, as I mentioned before. So if we start from the individual level, it’s what are our habits around mindset, professional fulfillment? How clear are we on our values? How aligned do we experience our lives and our work with our values? All of that can contribute to burnout or resilience at the group level. Let’s say the team level in a workplace, you know, and this comes back to the profound point you raised about discernment in community. The role of the community, kind of our work, family, the people we spend the most time with interact with the most, you know, kind of back to the parable. Do we have a version of our relationship that is supportive, compassionate? We care about them. We know about their values. We believe that they’re are wanting to support us. We feel that way about them. Or is it the opposite? Do we see them as a threat to our advancement, even survival? Do we not trust them? You know, there’s all these interesting studies about if you have one workplace friend, you’re going to be healthier, more engaged, advance more.

Leah Weiss 00:35:38  If you can build that at the team level, like this microcosm point in the storm that is massive for your resilience and then the broader culture within the organizations we function in. And how do those impact our our values, our ability to be socially attuned to others, our ability to feel like we can do our work and feel like we’re being seen and rewarded all of that. That there’s fairness. Interestingly, like people often hear about burnout and they think working too many hours is one of the biggest precipitates. Actually, one of the biggest precipitates is feeling like we’re out of alignment with our values, or that our workplace isn’t fair. People are rewarded for bad behavior. Or there’s inconsistencies. We talk about being this great culture, but in practice we’re actually like, you know, live and let die. So you can do work at each of these three levels. I spent the first very long part of my career focus on what can you do as individuals? Mindfulness, mindset, framing, emotional intelligence, social intelligence, all really good stuff.

Leah Weiss 00:36:50  But if we start looking at applying even that, like next level to what does it mean to bring your self-awareness into the team? So if you and I are a team with five other people that we can then share, what are our triggers, what are our values, and how do those align with the work that we’re doing together? How can we support each other and how can we even tactically, you know, do things the way we allocate work, the way that we assign blame and credit, the way we help each other actually be off when we’re on vacation. Because that comes down to your team often, like, totally. Do you have a way of give and take? And then at the culture level, there’s so much to do. But it’s tricky because it’s big, it’s amorphous, and it takes a long time. Three years is like what the number that most experts give to a culture change project in an organization. So if you want to talk about bang for your buck, focusing on the team level, I think is the way to go, which is why I’m putting my attention there.

Leah Weiss 00:37:54  Build your community. Build your support. Get that interactive part, but it’s manageable. We, a team of eight, can make a decision today to try something different and do that tomorrow. We don’t need to go get sign in, you know, buy in and approval from a lot of different people and all the alignment and socializing that comes with a culture change project.

Eric Zimmer 00:38:17  Yeah, that resonates with me for a variety of reasons, but one is sort of a middle way kind of guy, right? Between the organizational and the personal. What’s there, the team. Right. But to your point, it’s influencing our organization maybe a little bit, but it’s going to be kind of hard. But we have more influence on the team. And it also addresses some of those issues that are slightly more important than the personal. This gets back to discernment questions, right. You just mentioned, like, you know, if I have teammates who are toxic, right? There are people I know in life who see nearly anybody who doesn’t agree with them as toxic.

Eric Zimmer 00:38:56  Their self-awareness is such that it’s like, if you don’t agree with everything that I think, then you’re, you know, I’ve labeled you as the problem. You’re the toxic person, right? And then the other extreme would be the person who, you know, thinks that doesn’t matter who it is out there. You know, Genghis Khan could be on their team and they’re like, well, I really should work on my ways of relating to other people from a place of loving kindness. Right. And so it strikes me again, as you know, how do we find this middle ground? Do you find that it’s helpful to start with the individual work and be sure that you kind of have that in place? Or is it really something you can start kind of at all levels?

Leah Weiss 00:39:32  You know, when we’re talking within the context of a team, we want to remember that power structure influences. So the team has a manager or a lead, and that person will realistically have an outsized influence on the culture of the group.

Leah Weiss 00:39:48  And what’s particularly tricky is often the folks who are middle managers are at very high likelihood of being burnt out themselves. So there’s trust they’re probably not at the top of their interpersonal game. Maybe they’ve been trained to be a manager, or maybe they became a manager because they were a good individual contributor, but they never, like, learned the kind of art of managing other people’s work, social intelligence, communication skills. So to come back to your question, the methodology that I’ve developed and work with is a combination of the individual and the team. So the individual needs to get back an understanding that they can see of where they’re at with their burnout, their strengths and weaknesses, and not just their burnout in general, but their burnout proclivities and their burnout specifically in this workplace. Right. Which is an important part of the question. We were coming back to you before, how do you determine what’s me? What’s the environment? So having that understanding what’s environmental then at the team level, understanding where’s my team at with respect to burnout? Are we all clustered at the high end of the burnout spectrum? Is it a range? Are some of us in actually like a pretty solid space? How can they help the others? What’s the role of the manager in supporting resilience or contributing to burnout.

Leah Weiss 00:41:15  And then what I’ve been finding a lot of success with is if you take some of this data and share back with a team, hey, Group, here’s where you’re at with your sense of belonging and psychological safety in burnout. So each individual doesn’t have to take the burden of saying, I don’t feel safe here, or these are the ways that this team is not working for me, but you’re laying it back at the group level, but anonymously. So your starting point is the group to address this shared problem that no individual has had to stand up and own or blame the others for. It’s just this is what is in this group. And then giving a methodology within Team Health, there’s four pillars. And based on where you’re at, we suggest you work on the belonging psychological safety component first. Or we suggest you work on structured rest because you’re all exhausted. Nobody’s getting any time off. There are some basic kind of stop gap so you can take rest up and then address, you know, the next and the next.

Leah Weiss 00:42:18  And thinking in terms of the science and behavior change, which is don’t do everything at once. Pick a keystone habit and work there as a group.

Eric Zimmer 00:42:26  Yeah. You just sort of answered a question I was going to ask, which is a lot of discussions about team efficacy these days seem to have boiled down to psychological safety. I’m not that focused on team work or corporate work anymore, but I see that phrase all the time when when people are talking about team psychological safety. And my question was going to be, is that all there is to this? But it sounds like you just identified four pillars that are important psychological safety and belonging being just one of them. The other three you mentioned, I guess R&R, right? Is that just kind of the team culture around what hours we work, how much we work, supporting each other in being able to take time off?

Leah Weiss 00:43:03  Yeah, that’s the most kind of tactical of the four elements and it really is around. Also just having the basic conversations like I’ve got little kids.

Leah Weiss 00:43:12  I live on the West Coast. The hours that I really want to carve out and need to be with my family are this and yours are that. Because you’re in another time zone and this is your life? Like having some structure around those basic conversations goes a long way because people are driving each other mad with the meeting invite. Like, you know, that is my Friday at five, like, but you’re in another time and especially in this global workplace, right? So it’s some of that very tactical coordination or having blocks and processes in place. I’d say slightly more like nuanced. But also important is autonomy. So getting that balance right, which is going to be different for each individual on a team of do you have the right amount of support and flexibility if you’re being micromanaged, that’s probably driving you bananas. If you’re untethered, being told to do things that you have no support or resources for, that’s also really bad. So autonomy is a collective process of resourcing and teamwork. That is so often a big part of what’s driving people into the ground with burnout.

Leah Weiss 00:44:21  You know, they don’t have to be deep conversations, but get some really productive work done on that autonomy place pretty quickly. And then the other piece is awareness, self-awareness, understanding your own values. Understanding basic tools of emotional and social intelligence. But doing that at the team level so triggers, values, alignment, all of that work. And so these four when you put them together you know are really they capture a lot. If you look at the literature and all the different participants have burnout or resilience. So psychological safety super important but not the whole story. And also I think so many people get it so fundamentally wrong thinking like, oh, if we want to build psychological safety, we should all, you know, share really, really vulnerable stories that are traumatic for ourselves. And actually, like when I work with a team to build psychological safety, the starting place often has to be the sanctioning around. Let’s come to agreements around how we want to be together and what we’re going to do when there’s microaggressions and when people deviate, because you can do all the work to share and be vulnerable.

Leah Weiss 00:45:37  But if you haven’t made agreements about how you’re going to respond when someone is getting pushed out of that group for whatever element of their personality or whatever ism is at play, then you can’t build a psychological safety. So that’s also part of I’m like, no, this is not about trust falls and sharing all of our trauma with each other. It’s also like naming norms for like, how do we want to be respected and respect others? And what will we do when those are transgressed to signal that we’re not going to be complicit.

Eric Zimmer 00:46:10  But there’s nothing wrong with the good old trust fall, is there?

Leah Weiss 4 00:46:14  No. I mean, we all. Who doesn’t love a good? Who doesn’t love a good a trust?

Eric Zimmer 00:46:17  That’s right, that’s right. I keep trying to talk Chris into one with just me being there to catch him. But he won’t. He won’t. He won’t go for it.

Leah Weiss 00:46:25  He’s not having it.

Eric Zimmer 00:46:26  No. He’s probably taking lots of notes about, team culture based on this.

Eric Zimmer 00:46:30  I want to ask a question about job satisfaction a little bit. This sort of ties in. And if I’m straying too far outside where you feel comfortable, just say, I don’t know. But I see a lot of people and what they feel is that their work isn’t meaningful. And what they often mean by that is that it’s not directly helping another person in like, say, helping starving children. And so they feel like, okay, I don’t feel like my work is meaningful, and I’m always torn by that, by by sort of going, yep, you’re right. You really should pursue that because that’s the path. Or are there other paths? And this gets back to our question before. Do I change myself? Do I change the situation? But what are paths to make work more meaningful? Assuming that we’re in generally a good situation, right. Generally, like we’re doing work that’s at least like somewhat challenging, somewhat interesting, you know, that can engage us. But the bottom line mission isn’t, say, philanthropic.

Leah Weiss 00:47:34  I love that question. I think coming back to probably work you are well familiar with from a spiritual direction is, you know, the values work getting really clear about values and then taking that from the abstraction and looking for the opportunities to walk the talk on those values. So maybe we’re not working to end world hunger, but one of our core values is around community or compassion and really exploring what are the opportunities within the work I am doing, the people I am interacting with, how can I lean into expressing that value? And then one of the ideas that we talk about in the academic language of extra role behavior. So what are things that are not part of my core job description that energize me, that bring me meaning, that help me feel connected with who I am and want to be? And often it’s a little bit of investing in those. And coaches and managers can really help the people that they’re talking with to identify not just the values, but what are the opportunities. And it’s amazing how many times I’m sure you’ve seen this, that you have someone who realizes they want to learn some skill and service of a core value.

Leah Weiss 00:48:50  They start to spending an hour a week and it changes everything around for them. So this is a place where, you know, in having taught MBA students at Stanford for years, I’m always saying like, don’t look at it like you’re losing time from this person if you’re bringing them alive, then you are doing the right thing, but also doing the smart thing for the business. So look for the values, the extra role behaviour, which means you need to know each other, have real conversations, and have honesty to the point where people can, you know the work. That’s just like they’re always procrastinating. It’s miserable for them. Can you get to an understanding of what that is why that is? And then within the realm of reason, respond.

Eric Zimmer 00:49:34  Yeah. So I want to bring us back around to where you are today. So we described you burnt out at Stanford, you know, overwhelmed. There’s something you’ve talked about that I think is really important here. You talked about how in addition to all that happening, there was an enormous amount of internal criticism of yourself because you felt like based on all the spiritual practice you had done, that you shouldn’t feel this way, that you should be able to meditate your way out of it, or you should be able to, you know, have enough equanimity to handle it.

Eric Zimmer 00:50:05  So take us from here I am. I am in this place of I recognize I’m burnout. I’m overwhelmed. I’ve got all this internal negativity happening. And maybe give us the short version of, you know, how you got to where you are today. And then maybe we could talk a little bit about today, because the thing I’d like to hit today is you’ve gone from one classical place where people can burn out, which is academia, to another classical place where people can burn out, which is the startup world. So I want to talk about that. But but walk us through the change process a little bit.

Leah Weiss 00:50:38  Well, I first have to comment like, I just I want you as a spiritual director. I feel like I could benefit from these conversations is therapeutic. I think you’re really picking up on things about my experience that it’s taken me a long time to. In some of it, I’m still definitely grasping to formulate. Well, long story short, a couple of years ago we came up from California to visit some of our friends who lived in Portland, who for years had all been saying, you guys really need to be in Portland.

Leah Weiss 00:51:10  Like all the things we are hearing from you about as a family that you’re struggling with, like, and just hearing this from two of my oldest friends in the world, my husband’s oldest friend. So we came up and I just had this, like, physical feeling from the moment we got here of just like, decompression. You know, I’ve experienced that in a few places in the world where I’ve gone before that, you know, it’s like a cellular shift when you get off the plane kind of thing. And, you know, I think fast forward to today. I was just talking about this this weekend. I was taking a walk with a very close friend who’s a physician, public health officer and was just saying, for me, it’s so powerful that, you know, the places I’ve lived in the past. and it had my kids in schools, like, I didn’t feel people around me. To the degree that I do now, where there’s so many folks who have similar academic backgrounds or kinds of choices about where they’ve taken their careers.

Leah Weiss 00:52:18  A lot of other families that are like ours, with the mom, you know, working a ton and the dad working a ton to support the family and home. So we came up this weekend, decided, oh my gosh, let’s just jump. Let’s just do it. Our oldest son was starting kindergarten the next year. I was like, if we just do this now, he can kind of come right in the process. So we did. We just moved really, really quickly. And since that time, I’ve seen, you know, so many people in the context of the pandemic do this. It did seem a bit bananas, I think, to some people in our life to just make the change so quickly. But I was like, I’m traveling so much anyways. I can travel down to Stanford as opposed to traveling to go see clients wherever, and then also taking some of the financial pressure off, which sounds ludicrous for someone you know. But coming from California anywhere is less insane. So there was that whole side of it.

Leah Weiss 00:53:13  Now, to your point about the startup world, yes, it’s another kind of microcosm. Less than 4% of venture money goes to women founders, including if it’s a woman in man co-founder. So me and my co-founder, my former superstar student from Stanford, two women, two moms. We are definitely not in a system that is like set up by or for us. But I think this discernment and community, like my co-founder, is one of my dearest friends who I think has more character and integrity and social intelligence than pretty much anyone I’ve ever known, including a lot of like, spiritually well-known figures like, you know, not to overly put her on a pedestal. She’s just a really good person who we can talk about everything together. It’s like my other marriage. And so there’s a lot of stress, but there’s a lot of alignment and values, a lot of ability to have real talk and a lot of shared commitment to the team that we’re building is going to walk the talk. We’re not going to be an organization dealing with team health.

Leah Weiss 00:54:20  That is a hot mess internally. I’ve lived that, you know, country song before. I’m not doing it again. and she has her own version of commitment to that. So, you know, I do feel like I have the right resources in place, but there’s a lot of stress, a lot of frustration. And, you know, also continued like doubt that I’ll have to work through around being a middle aged woman in a role that is not conducive. But I kind of am excited to do that on behalf of like, that’s most of the world. We’re not, you know, and if we can’t build Team health or think about organizational health and perspective of a middle aged parent like, I don’t feel confident that a 20 something year old non parent is going to do it in a way that works for me or anyone I know. So I’m going to lean into the discomfort and hopefully have enough support and clarity about what I need to do from having lived through kind of untenable ness before.

Eric Zimmer 00:55:26  Yep.

Eric Zimmer 00:55:26  Somebody I interviewed recently and one of their books was talking about age. They were talking about patience. But the thing they said, which I thought was really interesting, was they quoted some study where, you know, far more businesses that go on to be, you know, a certain size were started by 50 year olds and 25 year olds. Like, it’s just our cultural lens is, you know, 25 year old startups. But if you zoom out from just Silicon Valley and you look broadly, you go, okay, being 50 or in your 40s are is not an impediment. It can actually be, in a lot of ways, a benefit. You and I are going to talk for a couple more minutes in the post-show conversation, because I do want to go a little deeper into entrepreneurship and burnout because you’re an entrepreneur. I’m an entrepreneur. I think we could have some interesting conversations, but we’re out of time for the main episode. So, listeners, if you’d like to get access to Lena’s post-show conversation, add free episodes, all kinds of other good things, and the joy of supporting something you care about.

Eric Zimmer 00:56:26  Go to one you feed. Join. Leah, thank you so much for coming on. It’s been such a pleasure to talk with you again.

Leah Weiss 00:56:34  Thank you for having me. It’s been great to spend time with you and your listeners, and it’s so appreciate the community that you’ve built and being able to visit.

Eric Zimmer 00:56:43  And just in case people are interested in the work that you’re doing with building team resilience, what’s the name of your company?

Leah Weiss 00:56:50  Skylite

Eric Zimmer 00:56:53  Perfect. We’ll have links in the show notes where people can go through and learn about that work if they like. So thank you Leah.

Speaker 4 00:56:59  Thanks, Eric.

Chris Forbes 00:57:01  If you’re enjoying the podcast, check out our weekly Bit of Wisdom newsletter. Every Wednesday, we send a short email with practical insights, reflections and takeaways, often featuring past guests. It’s a great way to stay inspired and support the show. Sign up at one UFI.

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Filed Under: Featured, Podcast Episode

The Nobility of Service: Finding Magic and Connection in the Smallest Gestures with Will Guidara

June 10, 2025 Leave a Comment

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What do a fine dining maitre d. A magician burying cards in a backyard and a toddler looking for Elsa have in common? They all show us that magic still exists. If we’re willing to care more, than seems reasonable. In this episode, Will Guidara, who’s a former co-owner of 11 Madison Park, which was once named the best restaurant in the world, the author of Unreasonable Hospitality and advisor on the hit series The Bear, shares how he transformed a restaurant into the best in the world not through perfection but through moments of radical hospitality. Whether it was sending out hot dogs on fine China or designing hand signals to pour water silently. It was never only about the food, it was about making people feel seen. This is a conversation about joy, about seeing service not as subservience, but as nobility and the kind of creativity that invites connection.

Key Takeaways:

  • The concept of hospitality and its significance in various aspects of life.
  • Insights from the restaurant industry and the transformation of dining experiences.
  • The balance between kindness and excellence in service.
  • The importance of making people feel seen and valued.
  • The idea of “unreasonable hospitality” and exceeding expectations.
  • The role of creativity in building meaningful connections.
  • The impact of self-care and generosity in service roles.
  • Navigating relationships and managing people effectively.
  • The value of criticism as an investment in personal growth.
  • The importance of community and connection in fostering relationships.

Will Guidara is the author of the New York Times Bestseller Unreasonable Hospitality, which chronicles the lessons in service and leadership he learned over the course of his career in restaurants. He is the former co-owner of Eleven Madison Park, which, under his leadership, was named the Best Restaurant in the World. Will is the host of The Welcome Conference, serves as a Co-Producer on FX’s The Bear, and is a recipient of the Wall Street Journal Innovator Award. 

Will Guidara:  Website | Instagram | LinkedIn

If you enjoyed this conversation with Will Guidara, check out these other episodes:

How to Connect More Deeply With the World with James Crews

How to Unlock the Secret Language of Connection with Charles Duhigg


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Episode Transcript:

Eric Zimmer 00:01:06  What do a fine dining maitre d. A magician burying cards in a backyard and a toddler looking for Elsa have in common.

Eric Zimmer 00:01:15  They all show us that magic still exists. If we’re willing to care more, then seems reasonable. In this episode, Will Gutierrez, who’s a former co-owner of 11 Madison Park, which was once named the best restaurant in the world, the author of Unreasonable Hospitality and advisor on the hit series The Bear, shares how he transformed a restaurant into the best in the world not through perfection but through moments of radical hospitality. Whether it was sending out hot dogs on fine China or designing hand signals to pour water silently. It was never only about the food, it was about making people feel seen. This is a conversation about joy, about seeing service not as subservience, but as nobility and the kind of creativity that invites connection. I’m Erik Zimmer and this is the one you feed. Hi, Will, welcome to the show.

Will Guidara 00:02:13  Thank you so much. I’m really happy to be here.

Eric Zimmer 00:02:16  We’re going to be discussing your book. That’s called Unreasonable Hospitality The Remarkable Power of Giving People More than they Expect. But before we get into that, we’ll start the way we always do with the parable.

Eric Zimmer 00:02:28  And in the parable, there’s a grandparent who’s talking with their grandchild, and they say, in life there are two wolves inside of us that are always at battle. One is a good wolf, which represents things like kindness and bravery and love, and the other is a bad wolf, which represents things like greed and hatred and fear. And the grandchild stops and they think about it for a second. They look up at their grandparent and they say, well, which one wins? And the grandparent says, the one you feed. So I’d like to start off by asking you what that parable means to you in your life and in the work that you do.

Will Guidara 00:03:02  Gosh, it’s a beautiful parable. I think everyone has two sides to themselves, and our ability to walk. The line that separates those two is often what determines our success. I think in the way that’s framed, it’s quite binary, right? You obviously want to be the wolf that is focused on kindness and love, and not that that is focused on greed and hatred or whatever other words you used in the latter.

Will Guidara 00:03:29  But I think where it gets more complicated is when there’s two sides of your personality where you actually do need each of them to feed your success, and where success comes almost because of the tension between them, not in spite of it. Yes. For me, in the business World. Those two sides are on one end. This unbelievable knowledge and passion for creating cultures where I am empowering and trusting everyone on my team, recognizing that unless they feel invited to bring their most fully realized selves to the table, we’re never going to be able to connect with the people we’re serving in the most authentic way possible. And then on the other side, this perfectionist quality to me, some of them is filled with OCD tendencies that likes to control as many variables as possible to ensure that as few things as possible go wrong. And without question, I will spend my entire professional life falling off that line in one direction or the other. But when I fall, that is not what defines me. It’s how quickly I can get back onto the line with humility and with vulnerability, and with the dedication to keep on trying to ride it as carefully and as considerately as possible.

Eric Zimmer 00:04:58  Oh, that’s beautifully said. There’s so many things in there that that I think are worth touching on. I mean, one is that idea that, like, we all fall off whatever line we’re trying to walk again and again and again, and I think the people who seem to stay on the line are the ones who just get back on quickly. Right. You just they’re falling off, too. You’re just not seeing it because their wobble is a little bit less. And then the second thing is I pick that up in your book too. You talk about these tensions that that you had. Another one was hospitality and excellence. Yeah. As a tension. And I want to get into those before we do. Why don’t we just spend a minute or two and, give listeners a little bit of your kind of, your background to today. So they have context for everything we’re going to talk about.

Will Guidara 00:05:42  Yeah. So I am most known or I was most known for the majority of my my career, for my success in the restaurant industry.

Will Guidara 00:05:53  I came up in restaurants. My dad was a lifelong restaurateur. My dad, who is still with us, is my greatest mentor, my best friend. The person from whom I’ve been inspired more than anyone else. And when I was growing up, I just wanted to be like him. I would have done whatever it was that he did for a living. It just so happened that restaurants, the thing that he did was something that independently, I fell in love with. I mean, at the age of 12, I always joke about this because I think it’s so funny. He my dad has taught me many, many things. Perhaps highest on the list is the power of intention. He’s a very, very intentional person, to ara Transcript

the point that at the age of 12, he asked me to come up with my to do list for life. And as ridiculous as that sounds, he was definitively being serious, And I know this because he gave it to me in my late 20s and it had three things on it.

Will Guidara 00:06:49  One was to go to Cornell University and study hospitality. And two was to open my own restaurant in New York City, and three was to marry Cindy Crawford. And I’d like to say that I did two out of the three, and then the third, maybe even better. And, it’s literally the only thing I did growing up. I worked in some of the best restaurants in America. I did go to Cornell. I did work for Wolfgang Puck and Danny Meyer, and eventually worked for Danny at a restaurant called 11 Madison Park, a restaurant that I bought from him. and over the ten years following the purchase of that restaurant, I turned that restaurant into the best restaurant in the world. and then I grew an entire company around it. And then I sold that company just a couple months before Covid, And, like many during Covid, retreated from the world for a measure of time and in that season had to decide what I wanted to do next. And sometimes I feel like the best way to decide where you want to go is to walk the path you’ve just been down.

Will Guidara 00:07:59  And so I wrote the book Unreasonable Hospitality, and now I do something very different for a living. The book was meant to help me decide what I wanted to do next, and it kind of became the thing that I went on to do, which is spending my work life trying to encourage as many people across disciplines to make the choice to be in the hospitality industry. Because I don’t care what you do for a living, you can make that choice simply through prioritizing people as much as you do product. And so you’re catching me at a really exciting season in life.

Eric Zimmer 00:08:34  I love that idea of everybody can be in hospitality because early on in the book you say talking about addressing questions you’ve spent your career asking. How do you make the people who work for you and the people you serve feel seen and valued? How do you give them a sense of belonging? How do you make them feel part of something bigger than themselves? How do you make them feel welcome. And I think for all of us, wherever we are, we can aim at those qualities with the people that are around us, whether that be our family or friends, the people we work with. If we have a big group of people around us, a small group, I think that idea of hospitality can run through everything we do. It becomes almost an ethos.

Will Guidara 00:09:17  Yeah. The US was a manufacturing economy. It is decidedly a service economy now. Yeah, I think three quarters of our GDP is driven by service industries, which means that it doesn’t matter what you do for a living. Let’s just start with work. You’re in the business of serving other people, and Now, whether or not you’re in the hospitality industry is solely based on. Well, the extent to which you work as hard to make them feel seen as you do in perfecting whatever service or product you’re selling them. And then in life, I mean, we should all be in the hospitality industry of life because I like to define the word often the word hospitality. And one of my favorite definitions is hospitality is being creative and intentional in pursuit of relationships.

Eric Zimmer 00:10:12  And wow, that’s a great line.

Will Guidara 00:10:15  And in a season where, gosh, there is so much division and people seem to be drifting further and further away from one another.

Will Guidara 00:10:23  I think the world would be a better place if we were all just a little bit more unreasonable in pursuit of those relationships.

Eric Zimmer 00:10:30  Yeah, you say in the book that the moment you start to pursue service through the lens of hospitality. You understand there’s nobility in it. And I just love that. I love that word in general nobility, because I think we can all act noble in our lives. You know, it’s not about kings. It’s about it’s about a state of being. But I think it’s a beautiful way of reframing serving others. Right. Because we could look at serving others as not good demeaning, which I didn’t have to do it, you know, but we all serve others. I mean, I whether we know it or not and whether we want to embrace it or not, and it’s far better to do it nobly and gracefully.

Will Guidara 00:11:09  I host a conference in New York City called the Welcome Conference, which has become, I’d imagine, the biggest hospitality conference in the country at this point.

Will Guidara 00:11:18  But years ago, perhaps in our first or second year, there was a guy who spoke. His name was Charles Mason. His family had for many, many years a restaurant in New York City called La Grenouille. It was this famous old school French fine dining restaurant, and in his talk, he acknowledged exactly that. That. I mean, when you’re growing up, no parent ever says, I really hope you’re a server one day, right? They always. You know, every parent, at least for a very long time. Like you want to be a doctor or a lawyer or a banker. And there’s almost this culture where we look down on people who give their life in pursuit of serving others. But the truly great among us are those that have the confidence to well, to serve and and don’t require the external validation of others to feel like they are the person they always wanted to be. But I also think that to really impact the world, leverage is one of the biggest things you need.

Will Guidara 00:12:22  And he he described it in this way, which I thought was beautiful and very easy to understand, that literally if you are trying to pull something. And if you are standing over something, trying to pull it up, you don’t actually have that much strength with which to do it. But if you get underneath that thing and you push it up, you can actually exert so much more force. I think there is nobility in service in answering that call to me to just show up for others instead of, well, only showing up for ourselves. And I think if you do it well with creativity, with grace, I think you can also make a really good living doing it.

Eric Zimmer 00:13:04  Yeah. There’s a line that gets used in the yoga meditation world a lot that has always rubbed me the wrong way. I understand what people mean by it, but they will often say, you know, let go of anything that isn’t serving you. Said all the time I get it like let go of the things in your life that are, that are problematic.

Eric Zimmer 00:13:25  But just the framing of it for me has always bothered me because I’ve always thought about like, whoa, hang on, shouldn’t I be putting at least as much focus on, like, what I’m serving? Yeah, well, I’m serving.

Will Guidara 00:13:36  You know, I talk often about self-care and its role in hospitality. I use the the metaphor of a water pitcher. If you’ve decided that you want to pursue a career in service and hospitality, regardless of industry, whether you’re selling cars or insurance or you’re a banker or whatever, you’re effectively constantly pouring water out of your pitcher into the glasses of others. And if you don’t pause every once in a while and refill your pitcher, you’re going to run out of water to pour very quickly. So I believe in all of that. And yet and never in a million years did I think this conversation would take me here, at least this quickly. I feel like some of the self-care industries with language like that. I think it’s just been manipulated to the point that people are using it in order to give themselves the grace to be selfish.

Will Guidara 00:14:36  That every single one of your relationships, they all better benefit you entirely. And if they don’t get rid of them. And honestly, that’s just not a world I want to live in. Like we’re creating fancy language that makes selfishness permissible, and I think it’s devastating.

Eric Zimmer 00:14:51  Yep. I just finished my first book, and I just turned it into the publisher a couple of weeks ago. And in it, I talk about this idea that there’s this phrase that’s always haunted me, and it’s that you’re the average of the five people you spend the most time around. And it haunts me because on one level, I think it’s true. Right. Like who I’m around influences a lot about me, but that assumes that the people I surround myself with are there as instruments to make me better versus relationships that I have. And so again, it’s another one of those self-help phrases that sort of makes sense. But when you when I examine it more closely, it troubles me a little bit.

Will Guidara 00:15:31  Yeah. Yeah. It’s also funny for me because I have a two year old and a four year old, and so I’m trying to figure out if they are 2/5 of who I am, then.

Eric Zimmer 00:15:45  They probably would be a good 2/5.

Will Guidara 00:15:49  By the way. I mean, you know what I will say, I have always brought a certain amount of levity to the way in which I. I try to show up in the world, but relearning how to look at life through the lens of a toddler, to appreciate so many of the things that we invariably begin to take for granted, is a pretty beautiful thing.

Eric Zimmer 00:16:14  I agree. My toddler is now 26 years old. Amazingly. but my friend and who’s the editor of this podcast, Chris, has a three year old. So I get to I get to re-experience some of it through him. And it is a beautiful thing. Something else that you say you learned, I believe, from Danny Meyer, although you can correct me if I’m wrong, was that you want to let your energy impact the people you’re talking to, as opposed to the other way around.

Will Guidara 00:16:58  Yeah, that was probably a mix of Danny Meyer, but also Randi Gerardi, who is my first boss  when I worked for Danny’s company, Randi went on to be the CEO of Shake Shack and is, in my view, one of the great leaders out there, full stop. And I’ve gotten to spend plenty of time with many of them, and he still sits very close to the top of that list. Randy was always just one of these guys that was unabashed in bringing all of his passion and enthusiasm to the team every single day. I, I think there’s this thing in both work and in life, honestly, where there’s a certain amount of us that will never cease being our high school selves. And in high school, you want to be cool. And the people that are celebrated for being the coolest ones are generally those that don’t try too hard, right? Like when I was in school, the ones that tried too hard, they were called nerds. The ones that were cool were the ones that like, were a bit more laissez faire about everything. And and it’s sad. And I think this is actually changing a bit generationally.

Will Guidara 00:18:08  But gosh, I want to celebrate the people that do try hard. I want to celebrate the people that are passionate And it takes an amazing amount of confidence and self-assuredness to just allow yourself to wear every ounce of your passion, to bring all of your energy to the table every single day. And when you’re able to do that, well, you can you can infect everyone around you with that passion. Public speaking is a big part of being a great leader. And yes, we should inspire people through our actions. But words also do a lot of the heavy lifting and restaurants. We have this meeting we call premium. We do it every single day, right before service with our entire team, before we unlock the doors. And that’s an opportunity to inspire, to get people fired up, to invigorate them. And too many people gauge what they give to that meeting based on what they are receiving from their people in that meeting, as opposed to recognizing no. My role is to energize them with my passion, not to become less energized because I’m not feeling as much passion in return.

Eric Zimmer 00:19:17  Yeah, well, I think that that goes for that sort of situation and lots of things in life in general, which is where how we treat somebody is tied to how they treat us. And I’m not saying that we should take this to some. Like I was going to use the word unreasonable, but you’re the wrong guy to use the word unreasonable with not not to take it to the point where, like, you know, we’re a doormat to people or we’re in abusive relationships. But I think there’s something to be said for here’s who I want to be. And this gets back to your dad and intention. This is the person I want to be, regardless of what I met with.

Will Guidara 00:20:02  Yeah. I mean, I’ll tell you this. And this is definitively one that I learned from Danny Meyer, one of my favorites of his isms. And Danny was a master of isms. These like little ways that he articulated the things that mattered to him, and in doing so, not only made them easier for us to communicate to one another, but in creating an ism around a core value or a tenant of his belief system.

Will Guidara 00:20:29  It was a meta signal to everyone that that was something that mattered to the culture at large. One of them was the charitable assumption, which is a fun way to say give people the benefit of the doubt. Here’s the thing, and I’ll use a restaurant metaphor for obvious reasons. If someone comes into the restaurant and they’re just acting like a jerk, you’re waiting on someone and they’re acting like a jerk. It happens, obviously. It’s completely natural, profoundly human, to decide that that person no longer deserves your most gracious Hospitality. The charitable assumption rather, though, would have you think this instead. Maybe that person is acting like a jerk because, gosh. On their way to the restaurant, they found out they just lost a loved one, or they learned that their spouse was cheating on them or some other thing like that. Maybe this person that’s acting like a jerk actually needs our love more than anyone else in the room. Now, sometimes the person was just a jerk. Right. But the idea is, my dad always says, ask yourself what right looks like, and then just do that.

Will Guidara 00:21:44  I’d always rather on the side of assuming the best than someone, and be proven wrong, than to assume the worst in them and be proven wrong.

Eric Zimmer 00:21:52  Agree 100%. There’s a story from a book. Maybe you’ve read it. Maybe you haven’t. The seven Habits of Highly Effective People and Covey tells this story of being on a New York subway car. And there are a couple of kids running just wild through the car. They’re kind of like the worst example of what a two and a five year old would be. And he’s getting frustrated with this dad who’s just sitting there, and he can tell that everybody on the car is frustrated and upset. And finally, it just gets to a point where he’s like, sir, I and I hate to I to bother you, but, you know, your children are kind of running wild. Maybe you could try and, you know, bring them in a little bit. And the guy looks up at him really dazed and says, oh, I guess they don’t know how to behave.

Eric Zimmer 00:22:39  Neither do I. We just left the hospital and their mother died. Oh, and in that moment, I mean, he tells it as a story of how quickly your paradigm or perspective can change. Because in that you instantly no longer is he a bad dad. You just want to help this guy. Yeah, but but that’s an example of the of the charitable assumption. Yeah. And I love what you said about. I’d rather think the best of somebody and be wrong, because I always think that if you think the best of people and you’re wrong, as long as you’re not getting horribly taken advantage of. No huge loss. But you begin to consistently be suspicious of people. There’s a huge loss, and that loss is to your own heart.

Will Guidara 00:23:25  Well, not only to your own heart, and obviously not only to just how you’re impacting people in an unnecessarily negative way, but the implications are almost endless. It holds back our creative output. It holds back the the flow of beautiful ideas that come into the world.

Will Guidara 00:23:43  I was doing a talk not too long ago, and we were talking about some of the stuff we used to do for people, and someone said, didn’t anyone try to take advantage of you when you were doing the stuff though? and yeah, of course they did. But gosh, if you limit what you’re willing to give to the world Old out of a fear that a few people are going to take advantage of your generosity. Like what a lose lose to let a couple bad apples ruin it, not only for everyone else, but also for you, in the same way that I’d rather assume the best in people and be proven wrong. I’d rather give a lot constantly, and be taken advantage of once in a while, than to never give it all and never run the risk of being taken advantage of.

Eric Zimmer 00:24:25  I think this would be a good moment to pivot to the title of the book, which is Unreasonable Hospitality. So I think up till now we’ve been talking about hospitality as a way of being in the world and of relating to other people, but you’ve tacked the word unreasonable in front of it.

Eric Zimmer 00:24:43  Talk to me about what that means.

Will Guidara 00:24:45  It really became my call to arms early in the evolution of the restaurant, as I endeavored to to take it to the top. I mean, here’s the thing. You look across disciplines, the people that are the most successful in every single one of those did so by being unreasonable, by being willing to do whatever it took to bring the most fully realized version of their product or craft or service to life. You think about everyone from Steve Jobs to Walt Disney to athletes like Michael Jordan. I mean, like, they’re unreasonable. They’re gonna do whatever it takes. That’s all I’m saying here. I’m just redirecting it towards how we make people feel. My favorite quote about hospitality. Most people at this point have heard it is by Maya Angelou. She said people will forget what you say. They will forget what you do, but they will never forget how you made them feel. Unreasonable hospitality is just being relentlessly intentional and creative and willing to do whatever it takes into those little moments.

Will Guidara 00:25:53  The moments that sit in the in-between, the moments surrounding not what you’re serving someone, but how you’re serving it to them. The the opportunity is to create a genuine and meaningful connection with the people that work with you and the people that you are collectively serving. And I think the big paradigm shift of unreasonable hospitality is it’s not just about being really nice. It’s about recognizing that to achieve any significant level of success, you need to develop practices and systems and a very thoughtfully considered approach. And the same is true when it comes to hospitality, that you can systemize graciousness through creating the right framework and the right culture, and making gestures of hospitality as easy as humanly possible for the people on your team to deploy. And if you approach all of those things as unreasonably as humanly possible, What you have the capacity to do is nothing short of extraordinary.

Eric Zimmer 00:26:58  Give us some examples of some of the things that you guys did at the restaurant that came out of this unreasonable hospitality mindset.

Will Guidara 00:27:09  There’s a position that I added to the restaurant that has certainly received the most fanfare, for lack of a better word, and is one of the stories in the book that people have resonated with the most, to the point where I’ve now seen this same position added to NFL teams and hospital systems and retirement homes and like multinational banks.

Will Guidara 00:27:33  The position is called the Dreamweaver and named after the iconic song by Gary Wright, which has always been one I’ve loved. And this was a position out of the team who had no operational responsibilities. They had nothing that they were actually charged with doing to power the service or the product or anything like that. They were just there, serving as a resource to help everyone else on the team bring crazy ideas and gestures of hospitality to life. And so they were there every single night with us just as a resource. And the stuff that we did with that person, it was it was wild. You know, little things that cost a little bit of money. Talking about Danny Meyer, Shake Shack was right in the park and so could be one of our servers overhearing one of the tables talking about as they were consuming like a caviar course that they smelled Shake Shack on the way into the restaurant and they couldn’t stop craving it. Easy enough. The Dream Weaver runs across the street to Shake Shack, gets a shack burger, and then as their pre entry before whatever their 30 day dry aged ribeye, we serve them a little slice of a shack burger.

Eric Zimmer 00:28:47  You tell a great story about how a guest mentioned mention coming to New York and, you know, hitting all the big restaurants they wanted to hit. But the only thing they didn’t get was a New York hot dog. Yes. And what you do is you run out and get him a hot dog. But my favorite part of that story is you bring it into the kitchen and trying to get this Michelin award chef to plate up a hot dog in an elegant way.

Will Guidara 00:29:12  Well, by the way, like you talk about how hospitality and excellence are not friends. And in the beginning of our conversation, you referenced the inherent tension between them. And that moment is a beautiful illustration of that tension. On one side, a chef who has spent his entire life trying to be celebrated for being the best chef that he possibly can be. And then on the other side, me just trying to do the right thing to make these people happy. Those are not friends. Always, right? It takes someone recognizing that the thing they’re trying to do is just a little bit less important than the other thing in that moment.

Will Guidara 00:29:50  And yeah, I mean, you know, we spend weeks, if not months conceiving of every single dish we serve days, if not weeks, prepping every ingredient that goes on to that plate. Years and years training every single one of the people that is touching every one of those ingredients as it gets cooked and sent down the line before it finally hits that plate and gets walked by. Someone who has spent years learning how to be the best dining room professional they can be, and then put in front of you on the table and explained in the most elegant way possible. And then right before that, we serve you a dirty water dog again. If you don’t have the right amount of confidence or the right perspective to understand what actually matters in those moments feel very demeaning. If you do, though, it’s unbelievably exciting because when you can create the kind of experience that is truly specific to the person you’re serving it to show that you care enough to listen, and then to do something with what you hear, illustrate that the experiences that are one size fits one where you are willing to bend your own rules solely in pursuit of making that person happy.

Will Guidara 00:30:59  Well, that is much more satisfying and definitively much more noble than creating a plate of food that looks pretty.

Eric Zimmer 00:31:18  One of the books that I’ve spent the most time with in my entire life is the Dao de Ching. It’s an ancient Chinese manual for living well that somehow also reads like poetry. Here’s an example of one verse that I come back to over and over through the years. If you look to others for happiness, you will never be happy. If your well-being depends on money. You will never be content. That kind of simple truth doesn’t just sound good. It actually changes how you live. If you let it. It’s simple, it’s direct, and it hits me harder every year. If you’ve ever been curious about the Dow, or just want some ancient wisdom that actually works in real life, I’ve got something special. I teamed up with Rebind to create an interactive edition of the Dow. I handpicked 40 core verses, translated them into plain, relatable language, and built them into a guide where you can ask questions and get my take in real time.

Eric Zimmer 00:32:17  It’s like having a conversation not just with the Dow, but with me too. You can grab it right now at oneyoufeed.net/tao. Now, if you’re looking for a little more clarity, calm or direction, I’d love to meet you there. You were just talking about sort of navigating a partnership between you and the chef who ran the restaurant, and you say in the book something about how to proceed in pursuit of a good partnership. And I just love this idea, and it’s to decide that whoever cares more about the issue can have their way. Nothing solves every problem, but that’s a really good way to think about something like who cares more? And we get locked into debates and discussions about things that maybe we don’t care very much about, but the other person really does.

Will Guidara 00:33:13  Yeah, we had all these different ways that we developed to navigate through moments of tension. I think it’s just important. Right. Like, here’s the reality. If you work alongside a group of like minded people who are as passionate as you are and wanting to be the best.

Will Guidara 00:33:32  That is a very, very special thing. It does not happen all too often and and therefore it’s something to celebrate, but also when it is the case there will be tension because when passionate people agree on a destination, they are invariably going to disagree on the right way to get there. You have to look at it and have it as something that you celebrate, because the tension implies that everyone just cares. But the more intentional you are in navigating through it, the better. Because I think a lot of people react to moments of tension in one of two ways. They either back away from it because it’s uncomfortable and they want nothing to do with it, or they just try to bulldoze their way through it and get the other person to agree with them. And each of those approaches is a waste, because if you can thoughtfully navigate through a moment of tension with anyone in your life, it will of course bring you closer to them. But together you can identify what is the best next step to take.

Will Guidara 00:34:34  And so, in not just that relationship and in so many of our relationships and work. We had hacks. One. If you and I disagreed on something, we couldn’t get through it. Either of us could at any point just say, hey, time out switch. Which meant I had to now start arguing for the thing you wanted, and you had to start arguing for the thing I wanted. It’s a funny thing about human beings. More often than not, we just want to be right. And the moment you start arguing for the thing you were just arguing against, now you want that thing to win. And it’s actually a beautiful shortcut to empathy, because you work more to more deeply understand the other person’s perspective. Sometimes that wouldn’t work, though, and in another one we call timeout and say third option, which meant if you want A and I want B, and neither of us can convince the other, maybe it’s because neither idea is good enough, and maybe it’s time for us to start working together to identify a third approach that’s better than either of the first two.

Will Guidara 00:35:32  But sometimes when you can’t get somewhere through a logical path of reasoning, then you just need to say, hey, who cares more? And maybe I should just let them have their way. And we used to say, I mean the words, this is important to me. We’re we’re sacred. But there is the side note, which is if you choose to do that, you cannot play that card too often.

Eric Zimmer 00:35:57  Right. Throughout the book, you talk a lot about the systems that you put in place to ensure both hospitality and excellence. And I was blown away by so many of these. Like the water thing. Tell us about the water. As somebody who really is thirsty all the time, I love this one.

Will Guidara 00:36:20  I mean, I just I love the intellectual challenge of trying to make every little thing you do just a little bit better. My dad also used to say to me when I was a kid, keep your eyes peeled. And what? What he meant when he said that was.

Will Guidara 00:36:36  If your eyes are open wide enough, you can really find inspiration everywhere, oftentimes in the most unlikely of places. And so yeah. Is that a baseball game? And I’m watching the, the catcher, sign to the pitcher and watching the pitcher shake his hand. The catcher shakes his head and the the catcher does another one. I’m like, gosh, sign language. It is such a remarkably effective thing. And I was like, I wonder if we can bring sign language into the restaurant. And so I started just studying the experience to try to identify where it could exist and have the most impact. And there’s two things. One, economy of time and economy of movement are both really important things to think about when you’re trying to make any experience better. Economy of time. Because invariably in a fine dining restaurant, there’s all these different things you want to do for the guest, and you want to squeeze as many little things as you can into the experience. But if the experience drags on too long, it’s just ruined economy of movement because you’re trying to create the serene, peaceful environment.

Will Guidara 00:37:43  And yet, in a fine dining restaurant, there’s a lot of people that work there. And if you’re not very intentional in how you’re moving them through the room to do all the thousands of little things that we do for people when they’re in our dining rooms, it can feel very chaotic. And so in water service, I found an opportunity to improve it both through the use of sign language. And so anyone who’s ever been to a restaurant knows that at the beginning of the meal, a server will come up to you and say, would you like Stillwater or sparkling water? Or would you prefer tap water? However, the restaurant has trained them to say that, and then that person needs to go and either themselves get the water or in a slightly nicer restaurant, find their busboy or their bus girl and communicate to them what the water is that they’re meant to give. It’s just a lot of unnecessary movement and a lot of wasted time. And so we just had sign language that if I’m talking to you, the moment I get your order, I’m signing behind my back to the busboy who’s across the room watching me because they knew I was about to go create your table.

Will Guidara 00:38:47  And I don’t know actually how to explain this by words right now, but like, if I move my fingers like this, kind of like dancing my fingers up and down and then sparkling water, if I went like this, it was ice water. And if I went like this, it was bottled Stillwater. And it almost was like a magic trick where I could actually still be talking to you. Right? And the person came over and started pouring the water that you had ordered from me. And these little moments, you know, Penn and Teller, teller has a quote. Sometimes magic is just being willing to invest more energy into an idea than anyone would reasonably expect. These little moments, These things, these systems that you can come up with that not only make things more perfect, but make things a little bit more magical. Not only do they feel good for the person on the receiving end, but they are so fun to conceive. I was talking to a friend of mine who’s actually a magician, and he was talking to me about this.

Will Guidara 00:39:47  He was brought in by a movie producer to train an actor, a famous actor who was about to take a role in a movie where he needed to know magic. And so this guy was brought in to spend an entire day with this actor teaching him magic. And they were finally done. And it was him and the producer and his assistant and the actor in the living room of the producer’s house. And they were done. And the producer’s like, come on, one more, one more. Give us your best trick. And he’s like, well, I kind of I kind of just did give you my best trick. He’s like, no, come on, you gotta have something else. And he’s like, all right, do you have a backyard? And the guy’s like, yeah, yeah. So they go into the backyard and he says to the actor, he’s like, all right, just look around the backyard and just put your hand in a direction. And now say a card. 234567, eight of jacks, clubs, spades or clubs? Spades, diamonds, hearts.

Will Guidara 00:40:44  They walk over there and then the guy takes out of his bag a shovel and he gives it to the actor. He goes, all right, dig. And the guy digs. And the card that he said is buried in the ground right there. And it’s this wild moment of magic like, oh my gosh, maybe magic is real. How the literal heck did this guy do it? But he’s not there just to do magic tricks. He’s there to teach him magic. So then he pulls up a video. The night before, he was relatively certain he’d get to the end of the day and the producer would say, give us one more trick the night before he went there and in a clock format so he could very easily in his head, remember where he had buried every card, buried all 52 cards in the ground, and remembered where each one was. He used some, like mine, like markers in the yard. So no matter what, where the guy pointed and what card, he said, the guy could massage it to get to exactly where he wanted to be.

Will Guidara 00:41:41  That is a moment that you’ll never forget. And it wasn’t hard. Yeah, it just required trying harder. And I think that’s just a beautiful thing. And I don’t know, so many people do things that are so unbelievably noble and so impactful. And if you do one of those things and you’re not working hard to imbue your approach to it with a bit of magic, I just think it’s a waste.

Eric Zimmer 00:42:07  That is such a great story.

Will Guidara 00:42:09  It’s fun.

Eric Zimmer 00:42:09  Yeah. And now I’m wondering how much magic can you learn in a day? Because I’d love to. I mean, if it’s only going to take a day of investment to.

Speaker 4 00:42:17  Be able to build you to be able to do some magic.

Eric Zimmer 00:42:20  I might sign up. I just assumed to be able to do any kind of reasonable magic was going to take a long time.

Will Guidara 00:42:26  No. By the way, by the way, there’s there’s a company called theory 11, and if you go onto their website, you can learn magic and you can learn the kind of things that you can do at a party that just they’re not only fun to do, but if you’re the kind of person that loves bringing other people joy, I just think magic is one of the most beautiful ways to do it.

Speaker 4 00:42:45  All right, theory 11.

Eric Zimmer 00:42:46  I’m sold. What would you say is the best example of hospitality that you have received? That really kind of blew your mind?

Will Guidara 00:42:55  Man, I mean, that’s a hard one, especially since I put out the book.

Eric Zimmer 00:43:00  People just go out of their way to blow your mind.

Will Guidara 00:43:03  It’s always the case. Restaurateurs love serving other restaurateurs. because they know. We know that those people will appreciate the energy you invested into making the experience special more than perhaps other people will. And now, with the book, it’s just really anyone who’s passionate about hospitality. So I can’t say the best, but I’ll share one that happened recently, which I think underlines a pretty beautiful idea. I was in Palm Beach with my wife and my then three year old daughter, and we were staying at one hotel, but, my wife is a pastry chef. She has a chain of bakeries called Milk Bar. And so we both love good dessert. And there’s a hotel in Palm Beach called The Breakers, which is celebrated for its key lime pie recipe, which hasn’t changed in 80 years.

Will Guidara 00:43:57  And it’s a secret recipe. And so we went. We left the hotel we were staying at and with our daughter, drove to that hotel for dinner to have the key lime pie. now the breakers, if anyone’s not familiar with it, it looks like a Disney castle a little bit from the outside. It’s big over the top. Gorgeous. And as we pull up in the car, my daughter Frankie says, daddy, is that Elsa’s house? Referencing Elsa from the movie frozen. And I, in a in a moment of poor judgment, said, yeah, babe, we’re going to Elsa’s house right now thinking that, okay, that’s the end of this interaction. And it was for a moment. But then we get out of the car and we walk into the hotel. She’s like, well, let’s go meet Elsa. Like, I’m not going to Elsa’s house without meeting Elsa. And I was like, oh. And so we go to the restaurant and I cheat ahead with the maitre d who was seating us.

Will Guidara 00:44:53  So my daughter and my wife were a few steps behind. I was like, dude, I need a little help here in 30 minutes. Can you just come back to the table and say to my daughter that you checked, but Elsa is actually away for a couple days, and she’s going to miss Frankie, but she’s so excited she’s here, and you just want to send her Elsa’s regards. He’s like, totally, dude, I got you. He does come back 30 minutes later and he does say that. But in addition, he. They must have had this stuff at the gift shop or something. He had a little, like, plastic pearl necklace and a plastic pearl bracelet and a little tiara. And he went over and gave my daughter all these things, from Elsa to Frankie, to just welcome her to her house and say how sorry she was to have missed her. I’ve been upgraded to some amazing hotel rooms, and I’ve been left some amazing bottles of wine, and I’ve been given some very, very thoughtful gifts.

Will Guidara 00:45:49  But that one will always sit close to the top. And the reason for that is, sometimes the best way to love on someone is to love on the people they love. And they made the most important person in my life feel unbelievably good, which, well, that’s the fastest way to my heart.

Eric Zimmer 00:46:09  That’s a wonderful story, and I love that. What? The line you just said, which is sometimes, you know, the best thing you can do is love on the people that someone loves. Because you’re right. That is very profound. The example that came to mind when you just said that was thinking about nurses. My mom has been in and out of hospitals a lot over the last decade, and there are some nurses that go just a little bit beyond. They’re not unreasonable. They’re not giving her princess necklaces. They’re just being a little bit more kind. But it it feels so important in those moments in a hospital like that with a the mother who’s not doing well, there’s so much that’s out of your control and you’re scared.

Eric Zimmer 00:47:00  They’re scared, everyone’s scared. And that that kindness just comes shining through. And I just, I as I think about that, them being kind to my mom is far better than anything they could do to me. For me, in that, in that moment. Right.

Will Guidara 00:47:13  I’m sorry that you’re going through that or that she is as well.

Eric Zimmer 00:47:16  Well, she’s doing okay right now. She’s she’s been, Well, I’m not going to jinx it and say she’s been hospital free for x amount of time. We’ll just leave it at. She’s doing all right for the moment. I’m going to see her in. She used to live in Columbus, but we moved her to Denver recently where my sister is, and I’m going to see her on Friday.

Will Guidara 00:47:34  So amazing. Now, I think the other version of of this is there’s been more than a few times where I will be someone, somewhere with my wife or my dad or something, and someone is trying so hard to impress me that the 3 or 4 of us will be standing around, and that person is only looking at me and only talking to me, and it completely ignoring the people that I really care about.

Will Guidara 00:48:00  And that is the opposite of the right way to impress me. Yeah, right. And then I’ve been with other people who I think they might be trying to impress me, but they basically ignore me and focus only on my dad or my wife. And that is the best way to impress me. Yeah. You know, like, I just think we’re we’re uncreative sometimes. And how we pursue someone because we don’t recognize that. Just think about the things they care about and pursue those things instead.

Eric Zimmer 00:48:33  I want to talk a little bit about managing people, because I think that the lessons that go into managing people that work for you are lessons that can be applicable in any area with people. And there was something that you said, and I think this is you got to be in our relationships. Careful with this. But you say that praise is affirmation, but criticism is investment in the workplace. What do you mean by that?

Will Guidara 00:49:00  By the way, I think that’s true in life as well.  It’s just there’s different rules that apply to it. I think that we’re in a season where so many companies are so focused on praise and ways that they haven’t been before, and gosh, that’s a beautiful thing. I think for a long time it was not nearly as significant a part of corporate culture as it needs to be. When you set impossibly high expectations, when you have your team working incredibly hard to achieve them and they do something well, you better be there to affirm them and to celebrate them, because people crave affirmation and we deserve it when we work hard and it’s just the right thing to do. And yet, I think in many cases, companies have become so focused on praise that they have lost focus on on how powerful and beautiful criticism is. Because yes, if praise is affirmation, criticism is investment. And I don’t think there are many things you can do that are more generous than being willing to step outside of your comfort zone for long enough to invest in someone else’s growth. Now it’s only an investment if it’s approached thoughtfully.

Will Guidara 00:50:16  And I have rules of criticism, and these are those that exist in the workplace and criticize in private, never in public. Like any message, it’s one you’re hoping they’re going to receive. The moment you criticize them in public. It makes them feel shameful, which puts up a wall and they’re no longer listening. Criticize the behavior, not the person. We conflate a behavior with someone’s entire identity too often in how we criticize them. And if someone is doing something wrong, we talk to them as if they’re a bad person when they’re not. They’re just doing this one thing wrong. Just talk about that. Yeah. to criticize Says consistently in that some people only criticize others when they’re in the mood to, or when they have the energy to. And what that does is sends very unclear signals about what right looks like. Because I could be doing something today and no one talks to me about it. I do the same thing tomorrow and now suddenly I’m in the wrong. And that’s confusing. And to be unclear is to be unkind.

Will Guidara 00:51:22  And there’s a bunch more of them. And. But the one that I think is very important. Oh, actually, I do like this one. Criticize without sarcasm. I think it’s what a lot of insecure people do in moments where they’re having to hold someone accountable is they they’re sarcastic about it, about it. They think if they turn it into a joke, it’ll be easier to receive. But you should never joke about something as beautiful as investing in someone else’s growth. That makes both people look bad. But the last rule circles back to where this started, which is if there is someone who works for you, you better be praising them more than you’re criticizing them. Because if you’re not, it means one of two things is true. You are just so focused on catching people doing things wrong that you are not focused enough on catching them doing things right, or that person shouldn’t work for you anymore, and you’re at fault for allowing them to still have their job. Now in life, the rules change and a lot of them are still true.

Will Guidara 00:52:26  But in life you also need to receive an invitation. Like if someone works for me, it’s part of my job to hold them accountable to a standard that I have set and they have chosen to work for me, ideally because they want to grow within my organization or they think they can learn something from me and I’m there to usher their growth. That is not the case in life. In life, I am not there to hold other people accountable, unless I’ve been invited to play a role in making them a better version of themselves. And I think that’s one of the most beautiful parts of mentorship, intentionally picking the people who you would love to see invest in your growth.

Eric Zimmer 00:53:09  All right. We’re nearly done. Is there anything you would like to talk about that we haven’t? That’s, like exciting in your life or ideas that are new to you, that you haven’t put in a book that are, you know, lighting you up?

Will Guidara 00:53:20  I mean, something that I, I’m having a lot of fun with this one thing right now, a buddy of mine.

Will Guidara 00:53:26  His name is Aaron Routier, and he lives here in Nashville, and he’s a Grammy Award winning songwriter, and he’s written music for everyone from Lady Gaga to a bunch of, like, really? I think he has like two number one hits on the radio right now, and I’ve known him for years. And about a month or two ago he invited me over to his his house. He’s like, hey, let’s spend an hour and write a song together. And I went and wrote a song with him. I believe one of the things I talk about often is how there’s a sacredness to the table. It’s one of the few remaining places where people will genuinely come together and put their phones away and lean across the table and connect, and we need more of these things that create conditions for connection. But for now, let’s protect the table at all costs, because it’s where a lot of beautiful things can come to exist. And we wrote this beautiful song called That Table and it ended up getting cut.

Will Guidara 00:54:26  I got my first cut as a songwriter within a few months of being in Nashville, and it’s coming out next month by this unbelievable band called The Lone Bellow. I bring it up for three reasons one, I’m just really excited about it. It’s fun for me too. I really do believe in talking about the power of community and what can happen when you gather together awesome people around the table and and choose to put the world on pause for a little bit. But three what it actually did for me I was not expecting in in farming, you know, you’ll hear often about crop rotation, which is certain crops deplete the soil of certain things. And so if you’re growing soybeans in a field for a measure of time, you need to plant something else in that field for a while in order to restore the nutrients required to grow the soybeans again. And I found that to be the case so powerfully with me when I invested even an hour of my life in a creative pursuit that was different from the one that I normally do.

Will Guidara 00:55:31  Yeah, right now I spend my life writing about and talking about hospitality, and I do that with, with television, with the bear, and I do it with my book and with my newsletter. But spending an hour doing something with no ambition to, like, win a Grammy or something. Actually made me feel more creative in pursuit of the things that I actually do for a living. And gosh, I just would inspire everyone to take a little time and invest it in a creative pursuit that they’re not trying to turn into a career, because I think it will make you better at the thing that you do.

Eric Zimmer 00:56:07  Yeah, I’m an unabashed fan of of that idea, and that’s got to be one of the most Nashville stories that’s ever been told. You just show up in Nashville and the next thing you know, you’re writing a song. I mean is very Nashville. And interestingly, I just I do these episodes that I give to to supporters of the show called a teaching a song and a poem where I, where I talk about I pick a song I love, a poem I love, and something I want to talk to the audience about.

Eric Zimmer 00:56:36  And the one I just did. I used a quote from the, Jeff Tweedy, who’s maybe you might know. Wilco. Their music features in the bare 100%.

Will Guidara 00:56:47  Yeah.

Eric Zimmer 00:56:47  Anyway, he has a book called How to Write One Song. And I used to be a songwriter about before I started this podcast. I was a I was a songwriter, not a not a not a successful one, but I wrote songs and I loved it. And over the last ten years or so, what I’ve done is I still make I still write music. All the all the instrumental breaks in the show are all Chris, my, my editor and my friend and I. So I still make music, but I haven’t written a song song. And I just recently was like, all right, I’m going to write a song again. And so I pulled the tweedy book off the shelf about how to write one song. Yeah. And so your story further feeds that sort of inspiration to do it. And we had an episode recently with the poet and author Maggie Smith, where we talk a lot about creativity in that way and just how wonderful it is to try and make things.

Eric Zimmer 00:57:43  And I love what you said with no reason. Yes, like I’m not writing a song so it will do anything. It’s not going to do anything. Maybe Chris will hear it. Maybe my partner Ginny will hear it, but it’s the act of it.

Will Guidara 00:57:58  But here’s the thing. It will do something. It’ll make your next podcast interview better. Yes, yes, it’ll make you better. And by definition, it will more positively impact the things that you are trying to do in the impact you’re leaving in the world. And I think that sometimes we try too hard to measure the ROI of every little thing we do, without understanding that we need to measure the ROI in, in.

Eric Zimmer 00:58:23  Holistic terms.

Will Guidara 00:58:24  And holistic terms. Yeah, yeah. And you know what? The other thing that I’m really excited about is when I worked on the book, as I’m sure you felt this, actually, you develop a practice of writing, right? Yeah. And you, you figure out what is the rhythm that works for you, and you sit down and you do it.

Will Guidara 00:58:41  And then the book was done, and it felt almost sacrilegious to stop doing that, because practices are really hard to start again once you stop doing them.

Eric Zimmer 00:58:52  Yes.

Will Guidara 00:58:53  And so the way I’ve done that is I now have a newsletter that I put out every two weeks. It’s called premium. It’s kind of like what I would be saying to my entire team on a nightly basis if I still had the restaurant, and it’s just something I love doing, and it’s one of the things I’m most proud of right now. And so anyone listening, check it out. You can sign up at Unreasonable Hospitality. Com.

Eric Zimmer 00:59:13  Yeah, I know exactly what you mean. Writing the book taught me something about my ability to create that I didn’t know before I did it. Yeah. Well, I think that is a great place to wrap up. Will, I’ve really enjoyed talking with you. The book was outstanding. I think even people who were not in hospitality would get a lot out of reading it. I know I did, and thank you so much for spending time with us.

Will Guidara 00:59:37  Thank you so much, man.

Chris Forbes 00:59:39  If you’re enjoying the podcast, check out our weekly Bit of Wisdom newsletter. Every Wednesday, we send a short email with practical insights, reflections and takeaways, often featuring past guests. It’s a great way to stay inspired and support the show. Sign up at onefeed.net/newsletter.

Eric Zimmer 00:59:59  Thank you so much for listening to the show. If you found this conversation helpful, inspiring, or thought provoking, I’d love for you to share it with a friend. Sharing from one person to another is the lifeblood of what we do. We don’t have a big budget, and I’m certainly not a celebrity. But we have something even better. And that’s you just hit the share button on your podcast app, or send a quick text with the episode link to someone who might enjoy it. Your support means the world, and together we can spread wisdom one episode at a time. Thank you for being part of the one You Feed community.

Filed Under: Featured, Podcast Episode

Embrace the Chaos: Finding Clarity Through Meditation with Henry Shukman (Part 2)

June 6, 2025 Leave a Comment

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In part one of this two-part conversation, we walked along the edge of paradox where effort gives way to ease and the search itself becomes the obstacle. In this second part of my conversation with Zen teacher Henry Shukman, the way begins to reveal itself, not as something we grasp, but something we live. We talk about awakening, the collapse of separation, and what it means to encounter reality directly beyond language, beyond self. And we find ourselves circling the same mystery from different directions, Henry through the Zen path and his app The Way and me through a new project with Rebind, which is a new AI powered dialogue with the Tao Te Ching. Different forms, different longing to meet life more honestly, more fully and more whole.

Discover a Deeper Path in Meditation – Looking for more than just another meditation app? The Way, created by Zen teacher Henry Shukman, offers a single, step-by-step journey designed to take you deeper—one session at a time. Get started today with 30 free sessions!

The Tao Te Ching is one of those books I keep coming back to. Ancient wisdom, wrapped in poetry, that somehow feels more relevant every year. Like this line: “If you look to others for happiness, you will never be happy. If your well-being depends on money, you will never be content.“Simple. Clear. Actually useful.I’ve teamed up with Rebind.ai to create an interactive edition of the Tao—forty essential verses, translated into plain, everyday language, with space to reflect, explore, and ask questions. It’s like having a conversation not just with the Tao, but with me too. If you’re looking for more clarity, calm, or direction, come check it out here.

Key Takeaways:

  • Exploration of meditation and mindfulness practices.
  • Insights on the nature of thoughts and their observation during meditation.
  • Importance of a structured approach to meditation.
  • Personal experiences and reflections on meditation journeys.
  • Discussion of the “inner radio” metaphor for understanding thoughts.
  • Techniques for enhancing present-moment awareness through meditation.
  • The significance of variety in meditation practices to cater to individual needs.
  • The role of moderation and balance in personal growth, drawing from the Dao De Jing.
  • The relationship between relative understanding and direct experience in Zen.
  • The transformative potential of embracing uncertainty and interconnectedness in life.


Henry Shukman is a poet, author, and meditation teacher who has guided thousands of students from around the world through mindfulness and awakening practices. A Zen master in the Sanbo Zen lineage and the spiritual director emeritus at Mountain Cloud Zen Center in Santa Fe, New Mexico, Shukman is a cofounder of The Way meditation app and founder of the Original Love meditation program and has taught meditation at Google and Harvard Business School. He has written award-winning and bestselling books of poetry and fiction, he has taught poetry at the Institute of American Indian Arts, and his poems have appeared in The New Yorker and the Guardian.

Connect with Henry Shukman:  Website | Instagram

If you enjoyed this conversation with Henry Shukman, check out these other episodes:

Embrace the Chaos: Finding Clarity Through Meditation with Henry Shukman (Part 1)

How to Find and Follow a Healing Path with Henry Shukman

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Episode Transcript:

Chris Forbes 00:00:07  Welcome to the one you feed. Throughout time, great thinkers have recognized the importance of the thoughts we have. Quotes like garbage in, garbage out or you are what you think ring true. And yet, for many of us, our thoughts don’t strengthen or empower us. We tend toward negativity, self-pity, jealousy, or fear. We see what we don’t have instead of what we do. We think things that hold us back and dampen our spirit. But it’s not just about thinking our actions matter. It takes conscious, consistent, and creative effort to make a life worth living. This podcast is about how other people keep themselves moving in the right direction. How they feed their good wolf.

Eric Zimmer 00:00:52  In part one of this two part conversation, we walked along the edge of paradox where effort gives way to ease and the search itself becomes the obstacle. In this second part of my conversation with Zen teacher Henry Shukman, the way begins to reveal itself, not as something we grasp, but something we live. We talk about awakening, the collapse of separation, and what it means to encounter reality directly beyond language, beyond self.

Eric Zimmer 00:01:23  And we find ourselves circling the same mystery from different directions, Henry through the Zen path and his app the way and me through a new project with Rebind, which is a new AI powered dialogue with the Daodejing. Different forms, different longing to meet life more honestly, more fully and more whole. I’m Erik Zimmer and this is the one you feed. Hi, Henry. Welcome back to part two of this conversation.

Henry Shukman 00:01:53  Great to be carrying on with you, Eric.

Eric Zimmer 00:01:55  If people want to know how Henry responded to the parable of the two Wolves. Go back to the last episode and it’s all there. I’m not going to make us do that again, so we’re going to jump right in. I ended the last interview with a little bit of a cliffhanger, and I said that even though I’ve been meditating for 30 years in lots of different traditions and lots of different teachers in your app, the way I had an insight that I had not had before. And so I kind of want to share it, and then we’ll kind of go into the conversation from there.

Eric Zimmer 00:02:30  And in the app, you do a great job of walking people through what sort of objects of meditation can be, or what you might notice as you pay attention to your present experience? Right. You can hear sounds. You can feel things in your body. You can see things with your eyes open, your eyes closed. You can hear things. But you talked about thoughts And thinking of them like an inner radio. And I have used that analogy a bunch of times to talk about how you can sort of just tune out your thoughts because I, you know, I may have gotten this from Stephen Hayes and acceptance of commitment therapy, but something about like, sometimes you could treat your thoughts like a radio in your neighbor’s house. You can’t turn it off, but you actually did something a little bit different, which was to encourage us to pay actual attention to the thoughts, to listen to them as if they were the radio. And up until now, every time there’s a thought, I may glance at it.

Eric Zimmer 00:03:35  And I’ve had teachers encouraged me to glance at it, but then you come back to something else. But in this meditation, that was it. It was the thoughts were you treated them like an inner radio. And I have to say, it kind of opened my mind in a new way.

Henry Shukman 00:03:50  Well, I’m happy to hear it, Eric. Yeah. You know, I remember, when I was a kid, I must have been five. Probably. Or maybe six. This was in the UK, in Oxford, you know, back in the late 60s. It would have been. And my parents, along with having kind of a modern transistor radio little thing box, you know, they also had this sort of ancient thing called a wireless set, which was a wooden big thing, maybe 2 or 3ft tall, which stood on its own. It had these actually, it still had these things called valves in it, which were these sort of like long, thin light bulbs, and they had to warm up.

Henry Shukman 00:04:29  So you switched it on. It took kind of five minutes for these things to start working. And then it was just a radio with almost like a kind of wicker front where the speaker was.

Eric Zimmer 00:04:38  I seen them, they’re actually kind of beautiful now.

Henry Shukman 00:04:41  Well, it was, it was, yeah. It was like a piece of furniture, you know. Right. And anyway, I remember I loved listening to it, you know, whatever was on it was fascinating. And it didn’t matter if it was, you know, music Musical people talking. And I remember this day when I was sitting next to it or kneeling next to it or whatever. I was right there looking at it. Hearing voices inside. And I had been assuming that there were little people in there. You know, I was young enough to have just thought, well, obviously, somehow I don’t know how it works, I wasn’t sure. I didn’t really think think it through. There’s got to be little, little guys in there talking, you know.

Henry Shukman 00:05:20  And then I suddenly had this realization. No, there aren’t actually people in that. But the voices are still happening. Yes. And so that I’ve often thought back to that moment as an insight into thinking, because if you’ve become a meditator, you get good at just recognizing, oh, I’ve been lost in thought. Yeah. And I think I was like that for years. I knew if I’d been lost in thought, but I hadn’t really stopped to. And I could have said what the subject matter was. You know, I was I was thinking of that conversation I had 18 years ago or yesterday or I might be having tomorrow or whatever it was, but I hadn’t really delved into what is actually happening. What’s the phenomenology? What are the what’s the actual concrete phenomena? Sort of concrete of thinking. And of course, it actually is describable. We typically hear voices. We hear talk in the mind, and we sometimes see images. This sort of video, you could say radio and sometimes video sometimes, of course, both like watching a movie.

Henry Shukman 00:06:31  But that moment from my childhood, it taught me something about thinking, which is that, I mean, later when I thought back to it, you know that, yeah, I can hear the talk going on in my mind. And Rather than being the equivalent to thinking there’s real people, there is sort of getting sucked into the the subject matter that the voices are talking about, so to speak. It may just be one voice across the commentary. So actually, to take that step back and there isn’t a real thing going on there. That is what it’s about. The real thing that’s going on is hearing the words in the speech in my mind, and I can sit and be aware of that and not be drawn into it. And I can also do this thing of sitting and being aware of the kind of place or space in the mind where that kind of talk arises. And I can sit there and and be aware that, well, no talk is arising right now. Oh, there’s a bit there’s a little snippet.

Henry Shukman 00:07:45  Yeah, I almost missed it. It almost caught me, but I just saw it. I heard it rather, you know. I was aware of it. So it’s that kind of apparatus of the actual machinery, as it were, of thinking. I believe it’s incredibly helpful to become aware of a because it’ll mean over time we get less caught up in thought and more therefore more present. But be because it’s another thing to be aware of, just like sounds out in the world, you know, it’s another dimension of of mindfulness. We could say, you know.

Eric Zimmer 00:08:24  Yeah. It really struck me in that idea of like, where in your head is that voice coming from? And the thing that I noticed even more clearly, I had noticed this before, but again, this sort of sharpened the picture for me was that thoughts happen almost at different volumes, too. Right. Like there’s ones that are very sort of insistent or loud, but there’s others that are just barely audible that are sneaking through in there.

Eric Zimmer 00:08:55  That’s right. And so when I started, like you said, to pay attention to the machinery, it was really insightful for me. And and talking about being present, that is present moment awareness. I mean, those thoughts are happening right now. And so by noticing that then I’m there. And so it was just a slight reframe, but it was making spending some time letting thoughts actually be the object of your focus, instead of the thing that pulls you away from what the object of your focus was. And for me, was was really profound.

Henry Shukman 00:09:35  Yeah, I’m glad to hear it. And you described it perfectly. And by the way, on that thing about where they’re arising, it’s something that I find sometimes is I kind of okay, I’ve got. I’ve got the zone in my mind where they’re arising. I’ve got it clear and I’m listening in there. I’m listening in there. And then suddenly I was, oh boy, I wasn’t paying attention. And another one snuck in at a different, slightly different place than I thought.

Henry Shukman 00:10:00  Yeah. Yeah. Oh, there you are. Right. So it’s, you know, we have to stay on it in a sense. But I totally think it’s it’s a worthy object of mindfulness. You know, it’s. And then, of course we can. Then we can bring in the heart area and the emotionality, the emotion tone in, in the heart area as well. And then we’ve got kind of a full picture of our inner experience. And we can be more aware and as we’re more aware we can be more accepting of it. So it’s got a lot of knock on benefits, you know.

Eric Zimmer 00:10:32  Yeah. So I’m going to ask you another question about the way the app, or what happens in the app, because what you have people doing early on is. noting mentally what’s happening. So, for example, if I were to just be sitting quietly, I might be like, you know, thought, you know, hearing a sound, feeling a sensation in my body. Right? I’m just kind of watching what pops into awareness.

Eric Zimmer 00:11:03  You have people noting it. This is a nerdy question just for me. But you often have people then repeat it. Like, let’s say I’m trying to focus on hearing externally. It almost sounds like you’re using the noting not just to note what you hear, but to remind you of what you’re trying to pay attention to. Say a little bit more about what’s going on, because it’s kind of a persona, but kind of not.

Henry Shukman 00:11:30  That’s right. It’s some sort of in some ways, it’s like some vipassana. There’s a strong Vipassana teaching from maharshi or in Burma to do this kind of labeling noting practice. There’s also places in the early sutures that they talk about this kind of labeling. But what essentially what it is is it can either be responsive labeling. In other words, when something’s happened, we want to just note to ourselves that it has been happening. That’s really helpful for bringing back our kind of calm, steady presence and mindfulness. But also we can use it to direct our attention in a certain direction.

Henry Shukman 00:12:09  So exactly like your example. Yeah. Yeah, we use it both ways. So for example, if we want to be paying attention to the soundscape, to, you know, what we’re hearing of the world while meditating, just a little light note here. You’re hearing or listening, you know, just occasionally repeated. It’ll just keep our attention on that. And, you know, we can make it can be we can get more and more absorbed in the soundscape if we’re consistently keeping our attention on it and it can become, you know, quite fascinating. We can get more curious about it. So that’s a really helpful thing. Yeah.

Eric Zimmer 00:12:46  So a couple things really unlocked meditation for me probably 12 years ago or so. I have been doing it. I’ve been doing on and off for 30 years, but there was a lot of off in the on over that time. Right. You know, go back 12 years. It’s before you have a thousand meditation apps. You know what I’m getting, I’m getting from books.

Eric Zimmer 00:13:08  And mostly what I’m getting is meditate for like 30 minutes a day or 20 minutes at a time, that kind of thing. And that was a long time for me because, you know, I’ve joked when I sit down to meditate, it’s like the the dark circus rolls into town, right? Like, it’s it’s not that way anymore. But it used to be that way, you know, like a sort of a and so trying to do it for that long was hard. And it was almost always breath as the anchor, which for whatever reason, is not a great one for me. And one day I heard somewhere, somehow. Go sit outside and just listen to the sounds. And all of a sudden I was like, oh, I get what people are talking about when they say that meditation is peaceful and enjoyable. And like, I had not really much had that experience. For whatever reason, the breath was a fight for me. but all of a sudden, listening to sound and just knowing what came up was pleasant, enjoyable, and it allowed me to steady my attention enough that then I was able to do things like breath, meditation and others. So sound was a really big one. You know, it’s it’s it has a special place in my heart.

Henry Shukman 00:14:24  Yeah, that’s beautiful to hear. I can totally relate to that. You know, there’s a thing about the breath. I mean, it’s it’s it’s standard practice across many traditions. You know, start with the breath. It’s here. It’s kind of very It’s in a way, it’s almost sort of transparent, you know. Yeah. It’s, you know, it’s there’s sort of what’s really there. Of course. Really what it is is just the sensation of the muscular sensation of breathing. But it can be very soothing in time. But it’s not a great it’s not always a great place to start for the for the reason. I mean, it could be a variety of reasons, but one strong one in my mind is that that is right. Where all our emotion is felt in the body is right where the breath is, you know, in the chest, the diaphragm, the belly.

Henry Shukman 00:15:08  That’s our zone of sensations of emotion, you know, the actual muscular, subtle contractions that go with different emotions. They’re right there. So breath will often take us to emotionality, and we may not be ready for that in our practice. It can be, you know, if people have trauma and, you know, probably most of us might do to some degree, you know, and it’ll will be kind of forced to to face it. And that may not be a good place to start. So here’s the thing. There’s so many kinds of meditation. There’s there’s so many approaches. There’s so many framings of it. There’s so many specific practices that that are that are in. You know, especially in Asia, of course, where it’s been a, you know, really much more developed than in the West. And, you know, somebody once I read this somewhere long ago, like to use the word meditation is about the same as using the word sport in the variety of things it could be.

Eric Zimmer 00:16:13  That’s a great that’s a really good analogy. And I agree with you because there are so many.

Henry Shukman 00:16:19  Yeah. So that thing of just one practice. Do it forever. Follow the breath or something like that. You know, there’s there’s pedagogical sense in that in certain ways. And of course, it might not be the breath. You could just listen for the whole of your practice. But on the other hand, there are arguments for having different practices and so on. The way we try to lead somebody through a variety of practices as a kind of foundation, you know, so they’re really building up the basics of, of a meditation practice. And, and I mean, just for one example, there’s one famous manual for meditation in the early Buddhist canon, the early Buddhist sutures, the Pali Canon. And that is, it’s only like a four page or maybe six page document. And it’s got 65 different practices, you know. So you know.  So and but we the, our idea in the way is like, let’s get you clear on some of the foundational practices and purposes, the possibilities of meditation.

Henry Shukman 00:17:23  So you’ve got a better grounding then, you know, gradually will develop and keep you moving through them all over the course of the pathway. So you’re getting a better grounding, you know, that’s that’s the logic in my mind that is behind our pathway. Really. You know, it’s that kind of exposure to, to to different foundations of practice.

Eric Zimmer 00:17:44  Well, what I think is really helpful and useful about that is I do think that exposure to different ways is important in the program that I teach used to be called spiritual habits. Now we call it wise habits. There’s a different type of meditation for every week to sort of expose people in the way that you do. But the thing about what I’m doing is basically I’m just dropping this thing in there and going, okay, well, if you like it, stick with it. Like what you’re doing is exposing people in a systematic way to these different things, but also keeping them on a track. Right. And we talked about the part of the problem today is there are a thousand meditation apps, and some of them have tens of thousands of different meditations that you can choose from.

Eric Zimmer 00:18:30  Yeah. It’s similar to the the Netflix syndrome where you you get on and you instead of watching anything, you spend all your time trying to figure out what you’re going to watch. Right. It’s a similar phenomenon. Yeah. So but what what we get with the way your app, what we get is variety, a sampling, but on a path and headed in a certain direction instead of random. And I think it’s that’s really helpful. And I think the other thing that it does is it gives people access to a teacher like you in the way you would have access to a teacher in real life. So, for example, I can listen to nearly any meditation teacher in the world has a few meditations out there, right? I can go listen to them. Yeah. But the thing about working with a teacher in anything, really, is that that teacher takes you along a path, you follow along a path with that teacher, and they’re sort of shaping that for you. I think what people get with the way, what reason I love the way is that you’re leading me on a journey.

Eric Zimmer 00:19:39  You’re not just giving me a meditation or two. You are. It’s like if I were working with you as a student and you’d say, do this now let’s do this. And hey, Eric, for next week, let’s do that. And. And so I think it it really does that very well.

Henry Shukman 00:19:54  That is the hope that it’s sort of a path of training you know. And of course there’s you know I know there’s no perfect way to do it. And you know and it’ll some parts people will like more. Some parts they’re like less. And there’s kind of nothing we can do about that. But if there’s just that incentive to keep going. Yeah. You know, my hope is that if somebody really just followed this, you know, in three years, they’d be in a different place. They just really would be because they’ve had three years of pretty consistent meditation, and they’ve learned a lot, and they’ve studied a lot about their own experience inward and outward. They’ve had glimpses of different dimensions of practice, you know, which is really important because a lot of people meditating, that’s great.

Henry Shukman 00:20:40  And a lot of them think, I just want to use it to dial down my stress, you know? And that’s great. And it can help with that. But man, there’s so much more. It offers, you know, these existential discoveries we can make under the rubric of awakening or getting into deep flow states and discovering more support in our lives. There’s lots of good things in meditation that are beyond stress reduction. So anyway, so I’m glad you say that, because the main thing I wanted was like, here’s why it’s worth keeping going and here’s what you need to do to keep going. Just hit the next one. Step by step. You know, it’s that simple.

Eric Zimmer 00:21:17  That’s that’s exactly it. I mean, you know, the book that I just turned into the publisher, the working title right now is how a Little Becomes a Lot. And that’s exactly what we’re talking about here, right. Is that you do a little each day. Yeah. And the thing about the, the philosophy of or the approach of little by little, you know, little becomes a lot is that those littles have to go in the same direction.

Eric Zimmer 00:21:43  Yes. A thousand different littles don’t add up to a lot unless they’re, like, focused in some way. Right? That’s the thing about it. And that’s what this app does. It allows you to do a little. Yeah, each day that is accumulating in a particular direction. And it’s what you would get working with a good teacher would be the same thing. Right? Each day is a little thing, but it’s headed somewhere.

Henry Shukman 00:22:09  Yeah. But look, it’s exactly it’s like if we if we’re on a program, it’s that much easier to keep going. You know, a program gives us a direction and it’s in many areas of life, it’s the same thing comes up. It’s like someone says, I really want to follow a spiritual path. Well, give me a step by step path. You know, like 12 steps or something. You know that we really have a path to follow. but actually, Eric, I don’t want to. I want to. We’ve been talking a lot about the way.

Henry Shukman 00:22:40  But let’s talk about the Dao, because that, you know, that is also the way. And if I was a complete sort of newcomer to the daodejing and really sort of had heard of it, but really didn’t know a thing about it, I’d really want a guy like you to tell me to show me the way in. Yeah. And I wondered if you might just be willing to speak a little bit about sort of favorite verses from it, you know? Sure. Yeah. And yeah, I’d love to hear more.

Eric Zimmer 00:23:22  I’ll read one. And this is one of the verses that has been my favorite since I picked the book up the first time when I was 18 years old, which was a long time ago.

Henry Shukman 00:23:33  Not that long.

Eric Zimmer 00:23:34  Well, it’s verse nine in some translations of the book. The verses have a name and others they don’t. In this case, I went with the name, and the one I came up with was an exercise in placidity. And it goes like this. If you keep filling a bowl, it will overflow.

Eric Zimmer 00:23:54  If you keep sharpening a knife, it will become dull. Care too much about money and you will never be free. Care too much about the opinions of others and you will bring ruin upon yourself. Do your work and let go of the results. The best path to peace.

Henry Shukman 00:24:13  Beautiful. Beautiful. Wow. Pearls in every line.

Eric Zimmer 00:24:18  Yeah, yeah. I mean, kind of all the way through. But that line about care too much about the opinions of others. When I was young and reading that, that hit me, I was like, oh, because I did. I mean, it’s part of being young, I think because you do care deeply about the opinions of others. For me, one of the benefits of aging and spiritual practice is I don’t care so much. I’m not saying I don’t care. I’m saying I don’t care so much. But I recognized in that line that that path wasn’t that wouldn’t work, you know, and I like the line care too much about money. It’s not about everybody cares about money.

Eric Zimmer 00:24:55  You shouldn’t not care about money. Care too much about it, though, and you’ll never be free. And that’s the idea of enough, right? Because if we don’t know how to say enough and so much of the Tao is sort of about enough, those first couple verses, you know, if you keep filling a bowl, it will overflow. If you keep sharpening a knife, it’ll become dull. That’s talking about not knowing when enough is.

Henry Shukman 00:25:20  Yes.

Eric Zimmer 00:25:21  Right. Yes. Talking about. Just give me more, give me more, give me more. And, I first was introduced to this book when I was 18. It did not stop me from descending into heroin addiction. But looking back, you know, these lines really resonate. I can see like, well, you know, addiction is nothing but really keep trying to fill a bowl, you know, that it’s actually the reverse is it’s kind of you, you keep filling the bowl and it keeps remaining empty, you know, in the case of addiction.

Eric Zimmer 00:25:51  But yeah. So that’s one of my favorite verses for sure.

Henry Shukman 00:25:54  Yeah, that’s absolutely beautiful. It makes me think of, you know, the Epicurean ideal of moderation. Yes. You know, Epicurus was he’s often mis mistranslated or misrepresented as being like Epicurean these days, you know, for a long time has meant sort of gorge. Yeah, yeah. But actually he didn’t he didn’t mean that at all. He. That’s really wrong. He’s just said that it’s okay to enjoy a good meal in moderation. Like it’s moderate. Your your your desire. You know, be in a balanced place. And it’s it’s kind of like the middle way. Yes. You know, in Buddhism like like in I mean, Buddha’s early story was that he was brought up in the lap of luxury and, you know, in the sort of consumerist Paradise, as it were, where you could have everything you could possibly want. Then he he woke up to the fact that he was going to die one day. The stories about how that happened, and then he got into the path of practice and went the entire opposite way to extreme asceticism.

Henry Shukman 00:26:58  You know, he was he at one point, he starved himself to the point. The sutra said he could see his spine through his belly, you know, and and birds nested in his beard and grass grew up through the mats. He was sitting on the mat he was sitting on for meditation. And that didn’t work either. He was about to die. And eventually Sujata, this milkmaid, came and brought him this very beautiful, refined kind of rice milk pudding kind of thing. And he ate it. And he felt better again. And he and he, he then decided to follow the middle way. You know, not extreme luxury and indulgence, not extreme self-denial. Just. And he actually said he wanted to trust his heart. Yeah. The heart he had as a child, you know, just trust it. And sure enough, soon after that, a week later, he awakened in a blaze of glory, you know?

Eric Zimmer 00:27:54  Yeah. No, I love the middle way. There’s a chapter in my book about it.

Eric Zimmer 00:27:58  I mean, there’s a whole chapter about just that idea. And in the whys habits program, we spend a week on it because I do think it’s so, so important now in my life, there are some things that there is no middle way on. Right? So for me, with addiction, I kind of am like, right, I just need the off switch. Yes, but if I wasn’t built that way, I would love I. A glass of wine would be lovely. Yes. Right. Yes. You know, a drink would be lovely. It’s. It’s one of life’s pleasures. It’s just in my particular wiring. Yeah. Yeah. You know, that’s one area I can’t do. The the middle. But so many things. And I think the other thing about the middle way, we talked a little bit about this yesterday about the sort of potentially things that seem like they’re opposite, like accepting right where I am and wanting to be different. And to me, the middle way is you can hold both those opposites.

Eric Zimmer 00:28:56  It’s not always just splitting the difference. Sometimes it’s holding the tension between two things that are different. And I think so much of life, if we look at it closely, is exactly that. You’re holding a tension between two things. I value my children, and I value my job. And those things are intention at times. Yes. And that’s not going to go away. And so becoming comfortable holding these things that seem opposite. And that’s one of the things the Dow does and Coens do too. They constantly flip you into this paradoxical state. Yes. You’re like, well, that doesn’t make any sense. But that training of getting comfortable with certain things, not making sense to me, also helps with the training in life of recognizing that you’re going to have to hold things that are in tension with each other.

Henry Shukman 00:29:50  Yes. That’s beautifully put. And I think there’s a there’s something I don’t know whether you resonate with this, but I feel that there’s when we’ve got two things in tension, the capacity to hold both actually gives us just a little opening to this space of awareness that is, is just a little bit larger than our ordinary sense of things.

Henry Shukman 00:30:15  And that that, you know, this is what koans do as well, is they. They’re often paradoxical or make no sense, but they’re kind of trying to push us in some way, or they have the capacity to just give us a little key that opens a little door that opens up more space. So suddenly. Yeah. Wow. I can rest in a place where these two apparently contradictory things are both true. And I can do that, you know, and I can. I find a piece out of that tension comes this slightly larger capacity that I didn’t know I had, or I didn’t know I was already kind of plugged into but hadn’t recognized it. And that’s the place. That’s a place that is actually dynamically peaceful. It’s kind of energetically energetic and peaceful at the same time. And that’s a great place to hang out, really in life if we can get there. But I’d love to hear more, actually on Dao. Can you can you give us a another highlight for you?

Eric Zimmer 00:31:16  Sure.

Eric Zimmer 00:31:16  I’ll do one more here. This one is verse 44. And it’s going to be similar because the Dow does that a lot, right? It’s not a linear book that you read and it just progresses you through ideas. It’s got these themes that circle around each other and you keep coming back. This one’s called fame and fortune. Fame or self-respect which matters more? Health or wealth? Which is more valuable? Gain or loss? Which is more painful? If you look to others for happiness, you will never be happy. If your well-being depends on money, you will never be content. And here’s my favorite, maybe my favorite set of lines in all of the Dow. If you are content with what you have, you can take joy in what is. When you realize there is nothing lacking. The whole world belongs to you.

Henry Shukman 00:32:08  That are that is glorious. And that’s that’s I think, I can think of many points in Zen that grow out of that, you know, because, as you wisely said in a prior conversation, you know, Zen is a kind of fusion of Buddhism, and Daoism is what happened when I think you put it beautifully.

Henry Shukman 00:32:30  When Buddhism, Daoism met in China in about the fifth, sixth century CE, you know, around about that time. And there’s like this I’m thinking of a line of a verse that was written to a koan, which is like the the holy hermit doesn’t need to be appointed a lord, the holy hermit, already he or she is one who already knows. You know that nothing is lacking. Nothing is lacking. So they have all the wealth in the world because nothing is lacking, you know. And so that’s. Yeah. That’s. I’m. It’s really. It’s. I’d love to actually be more versed in in the daodejing, I must say, because I think there’s, there’s so much in Zen that does come out of Daoism. It does, you know, and even things like the Cohen collections, they are like the koans, you know, as we said, are these little nuggets out of the biographies of great Zen adepts, you know, that became kind of meditation points that people could sort of sit with.

Henry Shukman 00:33:43  And sometimes it’s just a line, sometimes it’s a little dialogue, sometimes a little is an event, you know? but they’re, they, they can really trigger whether subtle or quite dramatic, they can trigger little or large shifts in the way we experience an ordinary moment. And they so they sort of reveal stuff about our ordinary experience that we might not have noticed and just that open that larger space, you know, and but what they do in these collections is they’ll they’ll state the cone and then there’ll be some verse on it, little, little verse, and then maybe a little commentary. That’s very like the E ching, you know, the you get the hexagram. I don’t know if people know it, but you know, the I-Ching, the Book of Changes. You get the hexagram, you get a verse, you get a commentary. It’s the same sort of structure, you know. And I wouldn’t be surprised if there are ancient commentaries that, oh, at least there’s lots of lines of the of the daodejing that get quoted throughout the Zen texts, you know.

Eric Zimmer 00:34:47  Yeah, yeah. And there’s and there’s commentaries on them in the same way from contemporaries or maybe not contemporaries. Exactly. Of of Lao Tzu, who we don’t even know if is one person. Right? Yeah. We don’t know what the Tao is exactly. you know, we don’t know whether it’s written by one person, whether it’s written by many people. There’s some legend around it. and I want to go to koans in a second, but I want to circle back to this verse real quick with this idea of, you know, realizing that nothing’s lacking. The whole world belongs to you. And I’ve had some of the kensho satori type Zen moments, these these moments of enlightenment. In my case, some of them have been longer than moments. But that line when you realize there’s nothing lacking, the whole world belongs to you, describes that state to me, to a very large degree. Right? There is this sense that there is nothing lacking at all, and that the whole world belongs to me and I belong to it.

Eric Zimmer 00:35:48  Yes. In this deeply felt sense. Yes. Yes. And so I love this little, little piece here because it points in a direction. Now we’re, you know, to have a moment where we realize that where we truly feel that nothing is lacking. That’s that’s a state that you know, you may get to. You may not get to, but you can get closer and closer to it. Because the way we tend to process everything is let me go get or do X, Y or Z, then I will be happy. And this points to the fact that there’s actually a different way to do that. That all the steps along the way could be cut out. I don’t need to go get X, I don’t need to get Y, I don’t need to get Z. This isn’t saying that there isn’t a realm in which all that stuff is really important, but there’s another realm. There’s another way of thinking, of being where you realize like, oh, I don’t need to do any of that.

Eric Zimmer 00:36:50  Yeah, right. And I think that’s what I think. That’s what the Dow points to. I think that’s what Zen points to. I think that’s what Buddhism in general points to. I think that’s what, you know, the Christian mystics point to is all this idea that from one view. Yes. Nothing needs to be different.

Henry Shukman 00:37:07  Yes. Yes. Yes. I totally agree. Put it beautifully. You could. It’s almost as if, like if we can just really inhabit this present moment, we’ll find that nothing was ever lacking. Yeah. And somehow we get conditioned in this way of not fully inhabiting this moment, because we’re so aware of the past and we’re so looking toward what is coming next. There’s one Zen master. She said. Somebody came to study with her and they asked like, well, what do you what do you teach? And she said, when I sit, I sit. When I stand, I stand. When I walk, I walk. When I arrive, I arrive.

Henry Shukman 00:37:50  And the potential student said, well, big deal, I do the same. She said, no, when you sit, you’re already standing. When you stand, you’re already walking. When you walk, you’re already arriving. When you arrive. You’re already leaving. It’s like we’re just not really in this immediate moment.

Eric Zimmer 00:38:09  We tend to treat most moments as things we need to get through on the way to other moments. And I think it’s important that we just stress real quickly. The the Zen idea. I don’t know if it’s I learned it in Zen of the relative, in the absolute meaning that there is a world in which your job, your your children, your health, all that matters. It’s important. It should be tended to. It needs to be tended to. This isn’t saying like, oh, everything’s perfect just right. But there’s another view where what we’re talking about is this inherent perfection with the way things are. And what, what I, what Zen has encouraged in me is the ability to move between those two.

Eric Zimmer 00:38:58  And then ultimately, you realize they are one and the same thing, but it’s very helpful for me because the thing that happens when people start talking, like you and I are talking about everything being fine the way it is, is that any anybody can manufacture a list off the top of their head of 20 things that are not fine about their lives, about the world as a whole, all of that, and that’s all valid. So I think it’s important. And that’s what I loved about Zen. And this idea of relative and absolute was it told me, you don’t have to give all that up. You don’t have to suddenly think like, oh, starving children. That’s not a problem. The world’s perfect, right? No, it’s not from this view.

Henry Shukman 00:39:40  Yes.

Eric Zimmer 00:39:40  But there’s another view. But most of us live 99.9% in the relative and almost none in that other. And what Zen training does or what, you know, going into the Dao more deeply and studying or taking the way app with you is it allows us to get a little bit more time. In that other view.

Henry Shukman 00:40:01  You put it beautifully. Yeah. There’s there’s a metaphor that’s in an early Chinese Buddhist document of the path of practice being like a cart track, and the cart track has two wheel ruts, you know, one for either wheel. And one of those ruts is the path of gradual development that is basically on the relative side. It’s like, you know, which we need to work on, just like you say, both in terms of our life and even when it comes to practice, we actually need to work on healing our healing our stuff, cleaning up, you know, what do they say? Waking up, but also growing up and cleaning up. You know, we got to do that work. And then the other wheel, right, is actually this absolute side that’s always already here. So you can’t really you don’t exactly get to it. That’s why I think last time we were talking about. Can I go and find it? Well, not really, because it’s already here.

Henry Shukman 00:41:00  Not only is it already here. It’s what you already are as well. You know you already are that. So you can’t really be looking for it. You’re. You are it, you know. But but to have both sides be manifesting in our practice, you know, we can work on the more relative side in practice and in life as we do. But if we’re on the meditative path, we’ll start to get little flickers of that absolute side, you know, and it can show up in a variety of ways. It’s just be it can just be a weirdo. Kindness that I didn’t I didn’t. Didn’t seem to make sense. And it can be even at times I got a lot of troubles and challenges that I’m really trying to work my way through. But I do my morning sit and it just cumulatively, I might suddenly get a moment standing at the water cooler, looking out the window, or getting into my car when suddenly this weird spell of volcanoes just sort of lands on me out of nowhere.

Henry Shukman 00:42:00  And it’s. And it’s beautiful. And it can go deeper as well, where, you know, suddenly I feel I’ll get a flash that in some way that’s hard to express, actually, but I feel it very strongly. I’m not separate from this world. I’m truly part of it. Not as an idea, but as a felt experience. And that can be very powerful. And really, you know, sometimes it’ll have us weeping with the beauty of it and, you know, the kind of revelatory love of belonging in a way. You said it so nicely, actually, you know, that, we how did you put it? The world belongs to me. But. Yeah, but also we belong to the world. Exactly. Yeah. So that that absolute side is a kind of, Man, it’s it’s such a beautiful thing to get to know more. It changes our perspective. And I totally agree with you. But it’s not about denying the relative side. It’s expanding our perspective and our and us, you know, in a sense of love and belonging that we can live with.

Henry Shukman 00:43:10  You know, and again, the middle way would be like, how do I ride both. You know.

Eric Zimmer 00:43:32  What I’d love to do next is have you give us a koan. We’ve talked about what they are. We’ve talked about what they can do. If you stay on the way. Your app, you’ll you’ll get to them, right? You’ll you’ll actually get to, do koans with you, and I think you’ll be modest about this, but in general, a lot, a lot. A lot of people would think you are one of the modern masters teaching the koan. You know, again, I know that you’re humble and you’re not.

Henry Shukman 00:44:06  You’re just you’re in trouble. Then if that’s the case.

Eric Zimmer 00:44:08  You’re going to brush that off. Nonetheless. It’s true. And so, you know, the app will get us to the place where you can. You can try that. But but give us a koan so that people hear one in the same way. We just gave them a verse of the Tao.

Eric Zimmer 00:44:22  Instead of talking about the Dao, we gave them a verse. Now give me a koan or give us a koan.

Henry Shukman 00:44:27  Okay, okay. This is, you know, they come in all shapes and sizes. Okay. So so this one, this is more of a narrative. It’s I’ll just cut to the chase of it. There’s a, there’s a young brilliant scholar called Darshan and he’s, you know, this is China, late eighth century. So he’s, he’s versed in Buddhism and he’s probably versed in Daoism as well, you know, and he’s got it down. He’s particularly big on this particular suture called the diamond suture. He knows it back to front. And he’s been he’s been studying hard, practicing hard. And he believes that you have to go through endless training in order to have a flicker of awakening to this stuff we’re talking about. And he hears about this. He’s he’s not yet a Zen guy. He he’s and he hears about this other school of Buddhism, the Zen school that’s saying, no, you just need to look into your own heart and you’ll find awakening is already there.

Henry Shukman 00:45:29  And he’s thinking, rubbish, they’re wrong. And he loads up this sort of barrow with scrolls and scriptures and commentaries, goes down to meet some Zen masters. And and the first one he meets, he starts having a conversation with him, and it’s in this monastery. And the guy is called Long Tan, which means, Dragon Lake. Actually, it’s the name of the master. He lives near a lake known as Dragon Lake. So that’s what it’s called. And they start talking late into the night, and it goes on and on. And he’s asking lots of questions of this master, and he’s really trying to trip him up and challenge him with all the stuff he knows from his scholarly studies. And eventually the master says long term, says it’s late. It’s late. It’s time we go to bed. And and Darshan sort of pushes aside the blanket hanging, hanging over the door. And it’s pitch black. And he doesn’t know his way around this monastery. He comes back and says, it’s pitch black outside and long time the master lighter paper lantern for him, which is an ordinary, you know, illumination device, like a candle in those days or something like that.

Henry Shukman 00:46:42  He lights it for him and he holds it out. And Diane is reaching to take this little lamp. And just as he’s reaching for it long term, blows it out. He blows out the lamp. And in that instant, Dyson has a profound awakening. And he he. The story is, you know, he’s trembling and weeping and sweating and. Shaking and bows to to this mushroom and says. I’ll never doubt your words again. You know. He’s suddenly seen something he’d never seen before. So. Okay, so that’s that’s the happy story, you know, the next day, Dyson gathers all his scriptures and burns them. And he says, you know it. You could you could master all the all the scholarly works in the world. It’s just like a hair in a vast space, that’s all. It amounts to a scholarly Understanding. So this is a perfect example of the difference between our ordinary sort of human understanding, you know, relative understanding which you can get very refined. But one moment of direct experience of the absolute and it puts it in such a different perspective.

Henry Shukman 00:48:01  So we sit with just that moment. He’s reaching for the lamp and the teacher blows out the lamp. That’s actually the koan. It’s just that. So as a meditator, we would sit, you know, get into our quiet, calm space. The meditation, however it’s showing up. We let ourselves be as we are soft body, loose body slowing down. And we’re starting to just settle in to being present. And then we drop the little story in. The master blew out the light, the master blew out the lamp. And you know, Darshan has probably seen a lamp blown out 10,000 times. But this is the first time he sees it in a most intimate way. In a way, he’s never seen it before. And so we just kind of rest with it, and we just let it gently work in our subconscious, in our unconscious. You know, we might sit with it on and off for weeks, letting it just kind of steep in us, and we just sort of see what happens.

Henry Shukman 00:49:13  We might get little moments that are that was a little unusual. What was that? That birdsong seemed inordinately close or intimate, you know, or wow, that sunlight is suddenly so beautiful. Just little glimmers and shivers of actually another way of being in the world, just subtly touching us, you know. And so, in other words, we don’t need to have the mind blowing awakening Experience that Deshaun had, but we can get little echoes of it. You know and and and it’s all there in just that moment. The teacher blew out the lamp is right there you know. So that’s a that’s an example of a of a koan, you know, and how we would, how we would actually sit with it and let it work on us. You know.

Eric Zimmer 00:50:08  Beautiful. That’s a that’s a great one. I’ve, I was sharing with you. I did, I got through a hundred koans. And when I say get through, what that means is your teacher gives you a koan. You go do what you suggested, which is you sit with it, and then you come back to your teacher.

Eric Zimmer 00:50:24  And something in Zen that’s called DocuSign, and you present your response. And I think that word present is is fairly accurate. Yes, you present and very often what you will get for a while is, you know, if your teacher is kind like mine was, I think you need to sit with that a little bit longer. I think less kind is no right. It’s just just a simple no. Or maybe. Maybe somebody whacks you with a stick, I don’t know. But but yeah, that’s that’s kind of the, the process.

Henry Shukman 00:51:01  Right. That’s what we do in the traditional, you know, student teacher context. But we can also just sit with them on our own. There’s no you know, they’re public property. And Cohen actually means a public case and so on the way people do actually write in and tell us about experiences they’ve had. And we always respond to everything that comes in. But, you know, they’re they’re very valuable just to, to, to to nourish our own sitting just like that, just by themselves.

Henry Shukman 00:51:33  You know, if we don’t have access to a teacher, you know, it works that way too.

Eric Zimmer 00:51:37  Beautiful. I’m going to switch directions a little bit and play a little game here. I’m not known for games, although for Something About You brings out the the, the the trickster in me. I remember when we were in, New Mexico last year, I read a passage from a book you wrote like 40 years ago that was very Zen. And you were like, I wrote that. So something about you makes me want to do things like this. So what I’m going to do is this I interviewed recently, a favorite of mine who is a old sort of new, old and new friend of yours, David White.

Eric Zimmer 00:52:15  Yes. And David has this wonderful book called consolations two and Consolations. One was the same thing. He picks a word and he writes about it. And he’s a beautiful, beautiful, poetic writer. He’s a poet mainly. And the last word in the book is Zen.

Eric Zimmer 00:52:32  So I’m going to read something he wrote about Zen and just let you then say whatever you want Afterwards. Okay.

Henry Shukman 00:52:39  Okay. Lovely. By the way, I actually got an advance copy. He just banged out that essay, and he sent it straight to me. I bet before the book came out, we had great conversations about it.

Eric Zimmer 00:52:49  Yeah. He described to me you guys were friends a long time ago in England. And he said that he at that time was teaching you about Zen. And then he described it as. Then Henry got in a Lamborghini and went tearing past me. And now he’s the Zen master. All right. This is what he wrote. Zen is surprising under its subterfuge. Zen’s biggest surprise is that it seems to have more confidence in the incoherent life we first brought to it than the one we are trying to replace it with.

Henry Shukman 00:53:29  That’s beautiful. Yeah. It’s one of the sort of, one of the little phrases that has come to be better known about Zen is not knowing.

Henry Shukman 00:53:39  Not knowing. There was a Korean Zen teacher who always taught. His book is called only don’t know, only don’t know. Just let go of the confidence that we have in ourselves having the whole picture do. We’re very you know, we can’t help it. We we we’re very convinced that we’ve got the whole picture of what this life is and how we navigate it and what this world is that we’re moving through. And Zen says, can we just even a little bit let go of the certainty that we have the whole picture? What is it like to make that little surrender? Maybe, I don’t know, the whole picture. And in that little fracture, that little crevice of uncertainty, of surrender, There’s a tenderness, there’s a warmth. There’s a promise that this very world as we know it, with all its troubles and challenges, could actually be our very own healing. It’s like there’s a great koan. The whole world is medicine. The whole world is your healing, you know. And what kind of sense does that make? Well, it’s like there’s a possibility coming back to what we were talking about earlier, of discovering that you belong to the world, that you’re really, truly of the world, and the sense of separateness from the world that we all, you know, kind of naturally, automatically almost live with.

Henry Shukman 00:55:25  You know, that is fair enough. That’s the relative side. And there’s another side to the absolute side where we’re simply not separate. But in our world of certainty about our situation, it’s harder for that side to show itself. So the what? I forget David’s language, exactly, but that inchoate confusion that we come in with that might be closer to the not knowing, to the release of my preconceptions and my assumptions that my preconceptions are correct. You know, sometimes I feel it’s like we’re walking on a cement floor, you know, walking through life on a on a bed. A foundation of certainty about the way things are and what koans want to do. What Zen wants to do is, put a little earthquake under us, a little upheaval under us, and suddenly we might find that that solid foundation And isn’t solid. And instead of it being horrifying, it’s marvelous. It can. Well, it can be quite a shock, you know, as well, but it’s a beautiful shock. You know that great teacher Rinpoche, Tibetan teacher, you know, he said.

Henry Shukman 00:56:52  One glimpse of emptiness is so horrifying that compassion naturally arises. And then he added, no one glimpse of emptiness is so marvellous that compassion naturally arises. Yeah.

Eric Zimmer 00:57:07  I think that is a beautiful place for us to wrap up. Henri, you, without meaning to actually cued what we’re going to do in the post-show conversation, which is I want to talk about emptiness. It’s a concept in Zen, in Buddhism, and it’s in the Dao a lot, too. And it’s a confusing one for a lot of people. So you and I and the post-show conversation are going to jump into that. Listeners, if you’d like access to that post-show show conversation, as well as a special episode that I make just for you. That’s called Teaching Song and a poem where I share a poem I love, a song I love, and an idea that’s on my mind. And you want to support the show, go to one. You feed, join and become part of our community. Henry. Thank you again. It is always such a pleasure.

Henry Shukman 00:57:51  It’s been a delight for me. Thank you very much for having me. I’m really honored.

Eric Zimmer 00:57:55  Thank you so much for listening to the show. If you found this conversation helpful, inspiring, or thought-provoking, I’d love for you to share it with a friend. Sharing from one person to another is the lifeblood of what we do. We don’t have a big budget, and I’m certainly not a celebrity, but we have something even better. And that’s you just hit the share button on your podcast app, or send a quick text with the episode link to someone who might enjoy it. Your support means the world, and together we can spread wisdom one episode at a time. Thank you for being part of the One You Feed community.

Filed Under: Featured, Podcast Episode

Embrace the Chaos: Finding Clarity Through Meditation with Henry Shukman (Part 1)

June 3, 2025 Leave a Comment

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In this episode, Henry Shukman discusses how to embrace the chaos and find clarity through meditation while exploring themes of self-development and self-love. Henry emphasizes the balance between effort and acceptance in spiritual practice, highlighting the interplay between sudden insights (satori) and gradual progress. He also discuss the importance of understanding one’s motivation for meditation and how a clear “why” can sustain long-term practice. The episode encourages listeners to embrace all aspects of themselves and appreciate the journey of personal growth.

Discover a Deeper Path in Meditation – Looking for more than just another meditation app? The Way, created by Zen teacher Henry Shukman, offers a single, step-by-step journey designed to take you deeper—one session at a time. Get started today with 30 free sessions here: www.oneyoufeed.net/theway

Key Takeaways:

  • The transformative power of meditation in personal growth.
  • The balance between effort and acceptance in spiritual practice.
  • The relationship between sudden insights (satori) and gradual development in meditation.
  • The importance of understanding one’s motivation and purpose in maintaining a meditation practice.
  • The role of structure in facilitating spiritual growth and practice.
  • The significance of embracing all aspects of oneself, including less desirable traits.
  • The dualities present in spiritual practice, such as self-improvement versus self-acceptance.
  • The concept of “wu wei” or effortless effort in meditation and life.
  • The value of recognizing life as a gift, even amidst challenges.
  • The interplay between various meditation traditions and their contributions to a well-rounded practice


Henry Shukman is a poet, author, and meditation teacher who has guided thousands of students from around the world through mindfulness and awakening practices. A Zen master in the Sanbo Zen lineage and the spiritual director emeritus at Mountain Cloud Zen Center in Santa Fe, New Mexico, Shukman is a cofounder of The Way meditation app and founder of the Original Love meditation program and has taught meditation at Google and Harvard Business School. He has written award-winning and bestselling books of poetry and fiction, he has taught poetry at the Institute of American Indian Arts, and his poems have appeared in The New Yorker and the Guardian.

Connect with Henry Shukman:  Website | Instagram

If you enjoyed this conversation with Henry Shukman, check out these other episodes:

How to Embrace Original Love on the Path to Awakening with Henry Shukman

How to Find and Follow a Healing Path with Henry Shukman

Effortless Mindfulness with Loch Kelly

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Episode Transcript:

Eric Zimmer 00:01:01  After ten solid years of daily meditation, I found myself drifting. My habit didn’t fall off, but my Y did. So in this two part conversation, I turned to someone who’s helped thousands rekindle their inner fire. Zen teacher, poet, and friend Henry Shukman. In part one, we talk about why effort can be the very thing that chases transformation away, how structure can actually liberate, and how to navigate the dance between ambition and acceptance. Henry is the creator of The Way, a unique meditation app that’s designed as a single unfolding journey. There’s no skipping ahead if you’re looking to reconnect with what matters without having to chase it, you’ll find something real here. I’m Erik Zimmer, and this is the one you feed. Hi, Henry. Welcome to the show.

Henry Shukman 00:01:52  Hi, Eric. It’s really great to be with you.

Eric Zimmer 00:01:54  I’m very excited to talk with you. I always love our conversations together. We prepared very little for this one because I remember when I saw you last year in New Mexico, I was there to help you launch your book with a book launch party. You and I went out to dinner the night before, and the experience I had was like of words just falling out of both of our mouths for like, two hours straight with like, no thoughts.

Eric Zimmer 00:02:18  So I was like, all right, I think we’ll be fine. Just trying that that approach again. So I’m really happy to have you on for this two part conversation. And we’re going to be talking about things that are all kind of tied together. You’ve got a wonderful meditation app called The Way we’re going to talk about that. I have a new project around the book, The Daodejing, that we’ll be talking a little bit about, and then we’ll obviously cover Zen, because Zen is what happened when Buddhism from India met Daoism in China, and Zen sort of emerged from that. So I think there’s lots of crossover here, but I think we do need to start the way we always do and give you a chance one more time to answer the parable. So in the parable, there’s a grandparent talking to their grandchild, and they say, in life there are two wolves inside of us that are always at battle. One is a good wolf, which represents things like kindness and bravery and love, and the other is a bad wolf, which represents things like greed and hatred and fear.

Eric Zimmer 00:03:18  And the grandchild stops to think about it for a second. They look up at their grandparent and they say, well, which one wins? And the grandparent says, the one you feed. So I’d like to start off by asking you what that parable means to you in your life and in the work that you do.

Henry Shukman 00:03:33  Yes. Thank you. And it’s really nice to have another chance to reflect on that, you know, and see how it’s changed. I’ll tell you, the thing that resonates most for me at the moment is, you know, in Tibetan Buddhism, they talk about feeding your demons. And I feel now that, basically my, as it were, the good wolf is very, very welcoming of the not so good wolf. That’s the whole thing is like, what is it in me that is totally capable of welcoming what is not so easy in myself and in the world to be welcoming, not in the sense of like letting it have free rein, but of giving it the home its always needed of being that, you know, that warm, welcoming host that can really accommodate all of me and all of this world, you know, and that doesn’t that not that we want the wild wolf, the dangerous wolf, the the the destructive wolf just running havoc, wreaking havoc and running wild.

Henry Shukman 00:04:42  But by actually loving it and giving it, in a sense, the love it’s always needed, really, it becomes a source of goodness itself, you know, and it it opens us up more. That’s where I’m at, really, with it. It’s gotta love it.

Eric Zimmer 00:04:58  Yeah. I was reflecting on something the other day that’s sort of similar to this, and I was reflecting on my relationship to certain parts of myself or internal voices, etc., that, that are just they’ve been around a long time. I don’t really have a whole lot of expectation that they’re going to completely disappear, but I relate to them so differently. And I like that idea of like, I more or less can well, you know, I figured that I finally figured that sort of balance out. I’m not saying all the time and I’m perfect, but I’ve I’ve gotten better at saying like, okay, I’m not going to fight you. Come on in. But you don’t have the run of the house either, right? Like we got certain rules here.

Eric Zimmer 00:05:41  And within there you can. You’re welcome. And and I heard people say this for a long time that your experience doesn’t necessarily change. It’s how you relate to your experience that changes.

Henry Shukman 00:05:51  I totally agree, and I think that’s that’s, you know, a big part of this path of meditative development. You know, that I’ve been on for, wow, an awfully long time. Yeah. You know, but it’s really it’s really is about that. And, and because we actually at certain phases in a meditation journey, we might think we’re going to just get to the mountaintop and rest there, you know, just being bliss the rest of our lives. But that’s not a full human life. You know, in my view, you know, so actually having but having, being able to be with all of life, you know, and more and more open and all of life, you know, both within and without, you know, both inside us and outside us, that’s really the richness. And indeed it means being able to relate to it differently in order to have that kind of openness.

Henry Shukman 00:06:46  Yeah, totally.

Eric Zimmer 00:06:47  Yeah. I remember Adi Ashanti once saying something? I think it was in one of our conversations, but it could have been elsewhere, I don’t know. He was talking about freedom. And we talk about, you know, freedom and liberation and the spiritual path and all of that. But he said, it’s not freedom from things. It’s freedom to experience things. And that was a that that really landed with me. I was like, oh, this isn’t freedom from sorrow. This isn’t freedom from difficulty. It’s that I can feel free to actually feel those things, allow them to be, not fight them.

Henry Shukman 00:07:23  Yes.

Eric Zimmer 00:07:24  And be with more of my experience.

Henry Shukman 00:07:27  Exactly. I’d say, what I see in in many people that I’ve, you know, I’ve been privileged to help guide a little bit on their, on their own paths. You know, there can be these watershed moments, these thresholds that, that we can cross where, you know, some cluster of attachments, you know, that have been Being binding us and making us relate to the world and experience in certain ways.

Henry Shukman 00:07:54  They can fall away and experience stays the same. Exactly like I was saying. But but the the way we respond is so different. We’re free now to respond to them our own way. And we’re not being we’re not being sort of tethered by the attachments that we’ve, we’ve, we’ve taken for granted and in many cases not even recognized we had because they’re so ingrained in us and so conditioned in us, you know. Yeah. So that’s a great way to put it. Yeah.

Eric Zimmer 00:08:26  So this raises a question I would like to talk about your meditation app the way I think it’s incredible, by the way. It is so good. And one of its defining features is that there is one path through and you cannot skip ahead. You, you you just have to go at one by one by one. And you were telling me ahead of time that it’s three. You have it’s a three year journey. And that you thought that was kind of how long it would it took to sort of set the baseline.

Eric Zimmer 00:09:01  And this got me thinking about a debate that happens in, in spiritual circles sometimes between sort of the epiphany, the satori, the instant enlightenment, and then this really long, gradual path. And I, you know, I’ve just got done, turned a book into my publisher that right now the title is how a Little Becomes a Lot. So it’s about this gradual path. And yet Zen does prioritize to some degree, these satori moments, these flashes of insight. And I’d love to talk about how those two seem like they’re different, but on a deeper level, they’re actually not. Or at least it seems to me they’re not. But I’d love to hear your thoughts on that.

Henry Shukman 00:09:48  Yeah, yeah, yeah, that’s a great that’s a great point. I mean, here’s here’s one way that it’s it’s been talked about traditionally is like, if you haven’t got the gradual slow little bit every day, the little, the little by little part, then if or when some major shift or even even minor shift, you know, but a shift happens.

Henry Shukman 00:10:14  It’s as if it’s like a beautiful seed that’s landed, but it needs good soil to growing, you know, and that gradual cultivation is is essential. And the way I see it these days is something like this. Like there are there are many people, I think who and there’s traditions, you know, that they’re really only interested in the gradual cultivation and that’s that’s just fine. And, you know, gradually, gradually, Actually, you know, one whole branches. Then the Soto side of Zen, you know, they they talk about Soto as the farmer. They’re gently, you know, they’re tilling the soil, they’re pulling weeds. They’re really caring for the the plot. They’re like a farmer just tending to it, you know, day by day, you know, and that’s that’s great. And gradually the invasive weeds get sort of weeded out, and the beautiful flowers and crops that we can eat and stuff, the nourishing stuff starts to grow and that that can be just lovely. But on the other hand, there are traditions that really are all about, hey, just realize what it’s what it’s all about.

Henry Shukman 00:11:27  Realize what’s really happening. Non-dual traditions like advice to Vedanta and other side of Zen. Zen, you know, puts more emphasis on that, you know, and that would be sudden discovery of a reality and awareness. A nameless, unnameable, a door. You know a way, you know. That’s actually always here. And can’t not be here. But somehow fundamental to all of experience. Perhaps to all of existence. But you can’t really get to it. Gradually. Because it’s a shift in perspective. It’s a sort of it’s a sudden seeing things. Not differently in that they change. But differently in that the vantage from which anything, everything is perceived has changed. Such that we’ve touched into something that’s always been here. That, you know, we could get into some of the things that this doesn’t do. Time. It doesn’t do space. It lets space happen. It lets time happen. But it itself isn’t sort of caught by them. You know, that has to be a sudden shift because you can’t really cross the ravine in two steps.

Henry Shukman 00:12:39  It’s just a sudden sort of leap. You know, a sudden shift in how we’ve seen. But if that isn’t, then landing in a life where we’ve got this steady practice, it can be a flash in the pan that doesn’t actually get integrated and doesn’t change how we live, you know? So it’s critical, I think, to at the very least, we want the gradual side. But the gradual side can be so enlivened and defied. You know.

Eric Zimmer 00:13:11  That’s a great word. We got 800 episodes plus. I don’t know if anybody’s ever used that word. Defied. Okay. Carry on.

Henry Shukman 00:13:21  It’s a good one. You know, we can suddenly, you know, make this discovery about our the nature of our existence, the nature of our life that we hadn’t somehow noticed before, even though it’s always been here. And it will have the possibility of actually changing our lives for the better, you know. So that’s I think personally I think it’s it’s really good that we know about that as a possibility.

Henry Shukman 00:13:48  You know, this sudden shift to the non-dual. But we don’t want to be chasing it too much because it’ll it’ll recede if we’re pursuing it, you know. but it’s okay to be aware that it’s a possibility. Meanwhile, we just do our steady practice, you know, and. Yeah, if that call it a flash of lightning, call it a seed, call it a fertilizer, whatever it is, if it drops in, fantastic, you know, and it will sooner or later, because it’s always here.

Eric Zimmer 00:14:19  Yeah, I think about it in a, in a couple of different ways also and, and a few analogies that you use. Right. Like you can’t jump the ravine in into jumps as you said, but you got to be near the edge of the ravine to jump it. Right? Which is what I think often gets missed in the just, you know, just wake up now idea, right? Is that the people who tend to wake up I’m not saying it happens all the time.

Eric Zimmer 00:14:45  You had an you had an experience that came out of the blue when you were a young man. And to your point, it didn’t really have a chance to land in any sort of fertile soil at the time. So it can happen. But for most people, it seems to be that they’re kind of at the edge of the ravine. They’ve worked to get there. And then I also sometimes think about it like a sort of like a baseball analogy. Right. Which is like you could say to a kid, like, all you got to do is put the bat on the you got a major league pitcher throwing it, you and all you got to do is put the bat on the ball and it’ll go out of the park. But more often than not, that kid might end up with like a, you know, a traumatic brain injury versus a home run because he’s he hasn’t practiced. And so and then the last thing I’ll say on this topic is, I’ve joked before that if you put the 24 year old version of me in my brain right now.

Eric Zimmer 00:15:38  He would think he was enlightened. He would. Because the shift would be so dramatic to him. Yeah. And so I think that’s the other thing that sometimes can happen to us on the gradual path is, yes, we have shifted. We’ve had big shifts. We just haven’t noticed them in the same way because they came about gradually, whereas the moments we’re talking about are very sudden and dramatic.

Henry Shukman 00:16:02  Yes. Yeah. I love that analogy, that idea actually, of bringing in, you know, I think of my own younger self, you know, 17 year old or something, putting him inside this experience. Now, he would be astonished by the peace, the quiet, the ease, the energy, the sort of smooth, not frantic. Yeah. You know, it’s a really it’s a really nice point. And I totally agree. So we’ve got to be we’ve got to be careful about, you know, how change happens, that it can be very subtle and gradual and powerful nonetheless. Yeah, and sometimes it can be.

Henry Shukman 00:16:40  Yeah. Blazing revelatory epiphany. Yeah. And that, you know. Of course. Well, that’ll really impress us, you know. Like, wow. This is really. Man, I didn’t know this was possible to see things so differently. And it’s. I feel like I’ve understood everything now and, you know, but actually that also has to be backed by such long integration and, and and all of that. So it’s, it’s really just I believe great to be kind of open to both.

Eric Zimmer 00:17:09  Yeah I agree. So I’d like to talk for a second about why to engage in a meditative or spiritual practice. I think it’s gotten to the point in our culture, and certainly people who would listen to this show where most people would say, well, I should be meditating. And that’s not a very useful framework anymore, right? Should be is not not really motivating. And this is actually relevant to me because after a decade or so, I mean, I’ve been meditating on and off for 30 years, but after a decade of really solid practice, I’ve noticed my practice get very wobbly.

Eric Zimmer 00:17:48  And I know all the stuff about getting a habit back on track, right? Like, it’s what I teach. It’s kind of my bread and butter. And what I’ve realized recently is that’s not the problem. The problem is back to motivation. And motivation has gotten a little bit of a bad word in the behavior change habit space because you don’t want to. They say you don’t want to rely on motivation, which is true. If we use motivation to mean whether I feel like or not feeling like doing something in the moment, but on its deeper level, motivation is why. And so I’ve thought we might talk about why practice? Because I think I need that refresher after having a really clear why on it. I think it’s gotten obscured for me.

Henry Shukman 00:18:37  Yeah. Yeah, that’s that’s beautiful. Thank you. I you know, it’s it’s a really good thing to come back to, I think quite regularly is why am I doing this if I have got a whatever I might be doing long term, why am I doing it? You know, a couple of reflections pop up right away.

Henry Shukman 00:18:55  I mean, the first actually is to the point about some kind of ebb and flow in enthusiasm for it and commitment to it. I think that’s a given. There’s just going to be more enthusiasm and motivation and there’s going to be less. I feel that too. You know, I get times when, oh, wow, I kind of just I want to be a different me that doesn’t meditate for a little bit, you know, just give me a little break, you know, and and to be able to accommodate that without having to stop would be my formula, you know. Like, how do I accept you? Quite rightly. I kind of had ten years of this. I need a I need. I need a little breather. I’m just not so into it right now. How do we accommodate that while not stopping? But to get to that, we’ve also got to have established why we’re doing it in the first place, what the longer term picture is. And I would say that on that side, there’s there’s a couple of different things also that come up.

Henry Shukman 00:19:57  One is the basic idea in Buddhism and probably, I would guess, most spiritual traditions, if not all spiritual traditions. And it’s really actually the heart of your your podcast name is that, you know, we need some training. We humans just need a bit of training because we can be quite destructive if we don’t have it. You know, all the research on the ancient evolutionary wiring that we still carry for being able to dehumanize other people. We can be very compassionate in a circle of concern, and that circle of concern can be made to have a really hard border. And the people that are outside it, they’re not only undeserving of our compassion, they’re undeserving of our wrath and our hatred and our aggression and our violence. A lot of research points into that is not really cultural. It’s human. That dehumanizing potential that we have, it’s part of our makeup, and it can be so damaging and destructive. And of all the creatures that have been dangerous to human beings over the last million or 2 million years, none has been so dangerous as human beings.

Henry Shukman 00:21:18  Right? You know, it’s all very well to feel good and say, no, I’m immune from my. Actually, we carry wiring that can be turned on. That dehumanizes other human beings. So what can we do to diminish the power of that to get a handle on, you know, if it’s developing? How do I manage that and not have it turn into vengeful destructiveness? You know, that’s part of it, to recognize there’s stuff in me that needs training. You know, and I always think, you know, I remember learning this in, in anthropology when I studied it, that indigenous cultures generally are kind of better at understanding and regulating and taming the negative side of us. They don’t just think, let’s propitiate the good. There’s a great God out there. Let’s propitiate him or her or whatever. No, there’s actually there’s other forces that aren’t so good. Let’s also propitiate them. You know, and that’s really wise to be. Again, coming back to that feed your demons thing to to not be just splitting off the dark side and say it doesn’t exist or, you know, we’re not interested in that.

Henry Shukman 00:22:32  Much better to be interested in it, to be aware of it and to be, you know, recognizing the shadow in young terminology and working with it. Otherwise it can be destructive. So that’s a whole training side. Right. And I, I just think that meditation is, you know, there’s many other ways of course, but meditation is a really good way for that because it’s cheap and it’s easy to do. You don’t need a lot of equipment, you know, you basically just need a chair or cushion, you know, and you need not a lot of time really. You know, even 20 minutes a day is going to I mean, I think even five minutes a day, if you’ve never done it before, will change things for you. You know, it’s good on that scale. But also, aside from that, the sort of training and taming kind of side. There’s this, you know, there’s this big matter of us being so engaged in our busy lives, in our activities and they may be great ones.

Henry Shukman 00:23:29  You know, they may be projects that we love, relationships we love, and all the rest of the good, good stuff. Or they may be not so good, but either way, we’re so invested in, you know, our outward lives that we miss. I mean, I talk about myself as well, you know, it’s so easy to miss this really important underlying fact of being alive, being able to just recognize the gift. Yes, it of course it has lots of challenges, but the gift of having this experience called life and to be able to unwrap that gift and receive it, yes, with its difficulties as well. But I mean, it’s incomparable from my point of view. You know, there’s no gift possibly greater than it, but if we never recognize it, it’s kind of a shame.

Eric Zimmer 00:24:50  I heard you say something along those lines somewhere else, which is, you know, it’s about being able to really receive the gifts of life. And that’s that’s quite something, as you’re saying, to like, really put a point on that, because I don’t know that most of us would experience life as a gift.

Ad insert point 24:59, 

Eric Zimmer 00:25:13  And to your point, this is not like Pollyanna, like everything’s always great kind of thing. But there is a there is an experience of being alive and if we can receive the gift of it is a really powerful and transformative thing. I’ve also heard you talk about meditation as a way of accessing an underlying well-being that’s not contingent on circumstances, and we’ll talk about the Dow in a little bit. But the the I was exposed to both Zen and Daoism around the same time in high school. I don’t think I understood a lot of it, but I but I somehow intuited that what you’re saying there. Right. I intuited that this was a system of being okay, having some degree of okay ness in a world that many times did not feel okay to me as a 17 year old. And I think I that that made it great sense to me because I was like, well, it’s obvious to me. Bad things happen in the world and they happen to everybody like it was pretty. You don’t have to be paying too close of attention to get that.

Eric Zimmer 00:26:25  You know, maybe I was more attuned to it than your average 17 year old, but that idea that there could be a way of being okay, even when things from a surface level weren’t okay, I think is what got me into all of this and probably keeps me in it.

Henry Shukman 00:26:44  That’s absolutely beautiful, actually. You put it so beautifully. I think that’s that’s in a way, that’s the heart of what I was trying to get at with that. Second, why for meditation is exactly that, that that we can we can greatly cultivate and develop our access to a fundamental. Okay, you know, which which it might sound like something I’ve got to create, I’ve got to develop a way of being okay regardless of conditions. But I think I think you’ve you’ve already just been nodding to this, that in the idea of the Dao and of the way, as it’s often translated in the Buddhist world, same concept basically, is that actually it’s always already here. So it’s not something that we develop, but we might develop our access to it.

Henry Shukman 00:27:38  You know, we might get more open to it. We might get might get more skilled at sensing it. So, so I always think like, yeah, I mean, you’ve heard me talk like this before, but I sort of think there’s two sides of meditation practice. One is kind of more conditional. It is developing ourselves and getting more mindful, getting more able to hold, you know, our difficult emotions, our stress or anxiety, our sorrow and grief and loss and fears and, you know, and also our joys when they come, you know, being getting better at sort of appreciating them and being with them. That can happen, but at the same time. On another hand really? It’s it’s actually more about uncovering an openness. It’s hard to say this because I can think of many times in my own life when I would never possibly believe this, but in a sense, even in the worst of conditions, it’s still present, you know? And I think of one Zen teacher, Blanche Hartman.

Henry Shukman 00:28:42  And she was in the in the late 60s. You know, she was she was in a, an anti-Vietnam riot. And she was right at somehow got pushed right to the front line, actually up against the riot shield of the riot police who were banging on their shields, yelling and screaming. And she found herself suddenly right in front of one of these policemen, you know, yelling in her face, beating his riot shield, pushing against her. And she’s jammed there at the front. And, you know, there’s a very intensely difficult, you know, situation that could have been highly traumatic. Somehow at that moment, she just got this flash. There’s no separation between me and him and and there’s no separation because we’re all part of one unfolding. We’re part of one reality that I don’t normally see. And now I’m. I’m seeing it. And so that, you know, that was a satori moment, you know, that was. Yeah, was an important step on her Zen path at Kensho, you know, and it happened in very difficult circumstances, you know, and I’m very moved by it really that we, we have that offered to us and we have that capacity as humans to, to taste a fundamental wellness of well-being.

Henry Shukman 00:30:10  Yeah. And I sometimes call it love, you know, because it is like a love to discover that level of belonging, you know, regardless of conditions. And but I also think it’s really important that we don’t sort of neglect conditions. We need to work on the conditions as well. You know.

Eric Zimmer 00:30:28  We’re talking about these what we could think of as dualities. We’ve talked about them a little bit here. We’ve talked about the gradual versus sudden. we just talked about being okay in any kind of condition and yet really caring about conditions. And there’s another one that you point out, and you talk about it when you talk about the fruits of being present and you talk about self-improvement as one outcome of that and self-love is the other. And I just got done writing my book, as I told you. And as it went on, it became clearer to me that that’s a lot of what I was talking about, about how we want to be the books about change, right? We want we change because we want to be better, different, etc. and how valuable and important that is.

Eric Zimmer 00:31:20  But at the same time, there’s an equal tension on that of allowing ourselves to be just as we are in this moment, allowing this moment to be just as it is. And I think that’s the same thing you’re pointing to here about the fruits of being present self-improvement and self-love.

Henry Shukman 00:31:36  Yes. Yes. Yes. That’s a great point, Eric. Exactly. Because on the one hand, there’s there is some self-improvement that we can work on. And even while we’re doing that, with more or less success, there’s also opening up to more self-love. And the paradox is that somehow the self-love accepting ourselves as we are can actually lead to more change.

Eric Zimmer 00:32:04  Right?

Henry Shukman 00:32:05  Yes. Even though we’re not asking for change, you know. Yeah. You know, if you see what I mean. So when we combine the two some self-development with self-love, the self-love makes the self-development so much easier, you know, and the self-development may open up more self-love or self, we could call it also, I guess self-acceptance, you know.

Henry Shukman 00:32:32  Right. But it could a deep a warm self-acceptance, not a not a kind of neutral. Well, I accept it, but actually really, I accept it. You know, there’s a there’s a tender warmth in there. Yeah. Some sort of some kind of I always think there’s a little bit of surrender. It’s like I, I surrender to the fact that, you know, I am the way I am. It’s I’m not fighting it so that I. Then the love can flow, you know.

Eric Zimmer 00:32:58  Yeah. I find that that balance such a important one in my own life. And I look at it even beyond like self-improvement, like a given example. So I am a guitar player and I play guitar at this point for no possible reason. It’s not going to give me anything else in life except what it gives me, which is to play music. And yet I find myself wanting to get better. And so there’s a part of me that’s like, oh, you shouldn’t. You shouldn’t do.

Eric Zimmer 00:33:31  You shouldn’t want to get better. You should just enjoy it. But then I came back. I come around to. But it feels good to get better, right? Like the actual practice of improving, of mastery. I’m nowhere near mastering anything in that department. But at that point. And so even in there, I find that I’ve got the blend right. There’s the I’m just doing this because I want to do it. And I also want to get better at it. And and for me, the thing I’ve been able to see the guardrail between the two. If there is one at all is the one of frustration. Meaning, if I suddenly am upset or mad or frustrated because I can’t play a certain passage. Okay, I feel pretty certain I’ve crossed the line. For me, my line of okay. Now you’re into the sort of self-improvement that isn’t actually helpful, and it is not very self accepting. But as long as I’m on the other side of that line and I’m still kind of playing, yes, then that desire is is I feel like it’s part of me and I, I want to let it be.

Henry Shukman 00:34:46  Yes. I love that. I think that touches on a little bit. You know what we’re talking earlier about the different relationship to experience. And I was saying, you know, we can have some some of our attachments can, in the course of practice, slacken or release that that would be one of those. There’s like or maybe that this relates to that. You know, the yeah, I do enjoy seeing improvement in my guitar playing, speaking for you. but I haven’t got this attachment lassoed around it like it must. I must be getting better. Then the frustration kicks in. If I don’t, I think you put it. I think it’s beautiful what you’re saying there, Eric, I really do. And I think that’s a kind of in my mind. That’s the sort of that’s like an x ray of healthy, happy, wholesome life that, you know, I’m not too demanding on myself or on life. Yeah. And, you know, and I’m appreciative appreciative of it sort of happening at all.

Henry Shukman 00:35:47  And I love seeing it get get better. Yeah. For me and for others, you know.

Eric Zimmer 00:35:54  Hey, friends, after over a decade of talking with world class teachers and trying just about every meditation app out there, I finally found one that actually takes you somewhere deeper. It’s called The Way. Unlike other apps that might offer a large variety of meditations. The way was designed by Zen master Henry Shukman, and it leads you along a clear, step by step path. Each session builds on the last, gently moving you towards something real. Peace, clarity, even awakening because you’re part of the one you feed community the way is offering you 30 free sessions to get started. Just go to one you feed net. Either way, it is truly the best meditation app I found. And Henry is the best teacher I know and I don’t say that lightly. Thousands of others feel the same. So feed your good wolf and join me on the way by visiting one you feed net. The way I think if we want to reference the Dow here is also this is a is a time to do it.

Eric Zimmer 00:36:59  And we’re talking about your meditation app the way. And then this project that I did with an organization called Rebind, where I created my own interpretation of the Dao from about 15 different sources. And then I teach about it and via AI you have a conversation with me about the Dao. It’d be like sitting down and having a conversation with me about the Dao. One of the things in the Dao that shows up again and again is the concept of wu Wei, or more accurately translated as effortless effort. And I think that’s partially some of what we’re talking about here, too. And it’s paradoxical right on its surface, like, well, it’s effort, but it’s effortless. It’s, you know, so I think but I think it kind of ties right in here.

Henry Shukman 00:37:44  I totally agree. Yeah. And by the way, Eric, I’ve, I’ve you kind of sent me a sort of, you know, a beta or a sort of work in progress of that. And it’s absolutely beautiful. I just love it.

Henry Shukman 00:37:59  And I want to have more time digging around in it, but what I’ve already seen was just marvelous because you’re you’re really very steeped in it. So it’s second nature for you to be talking about it and reflecting on it. And you very quickly clarify concepts that, that that I’ve had some exposure already myself in my life to, to the Dow and the Daodejing. But man, you really were clarifying things even, even I was getting. Oh yeah. Yeah. Lovely. That’s that and that, just that with hearing you talk about it and I threw a few questions at you. I Eric I loved what.

Eric Zimmer 00:38:35  How did he answer?

Henry Shukman 00:38:36  They were great. They were just. Yeah. You you were great. Yeah.

Eric Zimmer 00:38:41  The minute they gave me the thing to test out, like. Because what you can do is you can read the Dow and then you can ask it a question like I did the minute I got it, I was like, all right, I want to make sure this thing can’t go off the rails.

Eric Zimmer 00:38:53  So I’m like, Does Eric Zimmer have a secret love child? Does Eric Zimmer run a termite farm is, you know, just all the crazy questions I could come up with. And it it stays in its lane. It’s like, I’m sorry, I’m not going to speculate on Eric Zimmer’s personal life. So, but it is uncanny to me that this thing answers as I would now. There’s a reason for that, because I probably recorded about 12 hours of me talking about the Dow that got fed into this thing. So there’s a reason it sounds like me. It’s it’s learned a lot about me, but nonetheless, it’s still really fascinating to the whole eye. Thing is I this was my attempt. I’m a big believer like technology never goes backwards, no matter how much we might want it to. And so if AI is here, what are its possible good uses? And I felt like this is one of them, right? The ability to engage with teachers and education that you normally don’t have access to.

Henry Shukman 00:39:54  That’s that’s a fantastic point. Yeah. I wanted to ask you what would be your dream? User of it or your dream reader? You know, would it be because I could imagine little chunks, a little chunk a day, you know, like, I mean, somebody might want to devour the whole thing, but, you know, like with a koan in Zen. Yes. You might just take a nugget and chew with, chew that for a day and then another nugget or something like that. Do you have any thoughts on that?

Eric Zimmer 00:40:24  I do. I mean, I the ideal person would probably just be somebody who’s been interested in the Dao and has maybe even picked it up and been like, what am I reading here? Because it’s a strange book. You know, it’s much more a collection of poems than it is anything else in a certain degree. And in the same way, with poetry, you don’t. I mean, you can just read one poem, then the next poem, then the next poem, then the next poem.

Eric Zimmer 00:40:53  But it’s the slowing down that allows the poem to work on you. And so the way that I’ve engaged with the Dao over the years, and that’s why I chose that book, it’s probably my longest, most true book companion for the last 30 years. Like, it’s probably the book for me that I’ve, you know, gone back to most often over the years. And, and that’s how I use it is I just pick it up and I read a verse.

Henry Shukman 00:41:22  Yeah.

Eric Zimmer 00:41:22  Yeah. Or, you know, you could call it a verse. You could call it a chapter, you could call it a poem, but it’s, you know, it’s anywhere from, like, anywhere from like 30 words to 200 words. I don’t know, something like that. Yeah. and then read it and. Yeah, just kind of sit with it. So I think it can be used as a daily reflection type of thing if you want. It can be used as a I’m struggling with something right now.

Eric Zimmer 00:41:45  Let me pick this thing up and see if it has anything to say to that. and then there is a way, I think, that you can appreciate the, the thing as a whole and what it actually is. But I think that’s probably the best way I would approach it. I approach it like a poem. Yes, because it is so poem. I mean, that’s part of why I wanted to do an interpretation of it. And I use that term clearly not translation, because there are probably I at this point, I have one of the largest collections of Dao translations, probably in the in the country. I’m. That sounds ridiculous, but I’m sure there are some scholarly places that have a lot. But I’ve probably got 15 of them. Or 20 of them. There’s so many of them, and you read them and they can be very different from each other. And so this one was just my version. Yes. It’s not correct. It’s just my version. And I certainly lean on trying to keep the poetic where I can.

Chris Forbes –  00:42:43  The Dao. If you want to check it out for yourself, you can grab the interactive Dao experience Eric built with Rebind at oneyoufeed.net/tao. That’s one you feed.net/tao.  It’s a really interesting way to actually talk with the verses and with Eric as you read.

Henry Shukman 00:43:04  Hey I just had a thought. Did did we get to woo way. You brought it up beautifully a little earlier in our conversation. And I think you, you, you know, you invited a response from me and I’m not sure. Did I ever give a response to the woo way matter, did I do you think I did?

Eric Zimmer 00:43:21  I know, I think we kind of pivoted into the book and what it is. So I’d love to hear your thoughts on wu wei for sure.

Henry Shukman 00:43:29  Yeah. I mean, I think because it’s very central to Zen, this effortless effort. In fact, there’s a great, you know, these just to reference a koan right now that talks about it, talks to it to that topic, by the way, for for people who might not know a Cohen is a little phrase or little dialogue or little Action that’s come out of the biography of some Zen adept.

Henry Shukman 00:43:56  Usually in Tang dynasty China, which was 600 to 900 approximately in China. In some cases they come out of very early Buddhism in India. They’re a kind of an integral part of the sort of lore of Zen, or Chan, as it was called in China. And there’s one of them, a famous Zen teacher called Jiaozhou in Tang dynasty China. He was, when he was a young new student, talking to his master, he he asked him, what is the way? And his teacher was called Nanshan. He said, ordinary mind is the way. Your ordinary life, your ordinary experience, that is the way. And then Jiaozhou, he was said to be 18 at the time, a bright young guy. He said, well, well, should I, should I turn towards it? In other words, should I try to be? Should I be trying to find it? Should I be looking for it? Trying to find it. And his teacher says if you try to find it, you go against it.

Henry Shukman 00:45:02  So? So so then Jojo says, well, what should I do? How will I ever know if I have found it? Found it. And the teacher says it’s not about knowing or not knowing. It’s beyond either having it or not having it, knowing it or not knowing it. And so that’s actually that little dialogue is really nice illustration of woo way. He doesn’t say give up, don’t be here. Don’t be practicing. Don’t be on a path of meditation training. He just says, don’t be trying to find it. Yeah. Because you know if you do, you’re going against it. You’re sort of automatically, in a sense, pushing it away or you’re automatically looking the wrong way if you’re trying to find it. And so I think this almost ties together, like the Wu Way, as an approach to effortless effort. We’re not really trying, but we’re not disregarding either, you know? Right. And it also ties in the enjoying the guitar playing and enjoying getting better.

Eric Zimmer 00:46:06  Yes.

Ad insertion 46:34 

Eric Zimmer 00:46:34  I don’t know how you say this word. I’ve never heard it said. I’ve only seen it written. Sinologist. For somebody who studies ancient China. Do I have that?

Henry Shukman 00:46:41  Yes. I’ve heard it as sinologist.

Eric Zimmer 00:46:43  Sinologist? I’m not even going to pronounce his French name. Bellator is the last name he says. Woo way is a state of perfect knowledge of the reality of the situation, perfect, efficacious, and the realization of a perfect economy of energy. Now, I don’t love the word perfect in there because I don’t, I don’t. I don’t know that such a thing exists, but I love this like it’s, you know, the reality. You pick the most effective approach and the one that uses the least amount of energy.

Henry Shukman 00:47:17  that is beautiful. And I got to say that that went deep into Zen. That that. Yeah, that’s what you said. I’ve, I’ve actually never heard that puts a perfectly in that particular formula. Yeah. But it reminds me of a story of one Zen master who was woo men.

Henry Shukman 00:47:36  Woo men. Waka. He was he was he was asked there was a severe drought in a region of China, and he was invited to come. And what he was actually hired to come and help with this drought situation. And he was supposed to do what a sort of spiritual guy would do at that time, which was kind of chant, certain dance. Yeah, little dance, the rain dance, you know. And he instead he just sat there and the people who made him, you know, brought him all this way to help them, you know, said, what are you doing? You’re just sitting here. And he said, I’m busy not influencing anything. So that’s that’s exactly it. He’s he’s he doesn’t think he’s sort of just idly wasting his time. He’s not doing anything and that is his doing. So it’s also sort of woo way that’s deployment of perfect or minimum energy. Yeah. Total assessment of the situation in his mind anyway. He knows what he’s vibing into, let’s say, or something climatological or whatever.

Henry Shukman 00:48:49  And, It’s the most efficacious thing. It’s like. I don’t know. I know it sounds a little bit. Definitely weird and abstruse, but. But actually, I think he felt he was doing those three things at that time. The efficacy, the, the deployment of energy and the understanding, the knowledge of the situation. You know, it’s all right there just in his being, right?

Eric Zimmer 00:49:16  Yeah. I think there’s this other element of of Wu Wei in a, a more direct way of thinking about it, which is around recognizing that we often make things worse. Listeners have heard me joke before that if I was going to market what I do in its most honest form, it might simply be how to not make things worse, which I’m not sure is a good selling point or not. But when you realize our infinite capacity to make things worse, you actually go, oh, that’s actually kind of a big deal. and so I think of that as we also is recognizing that sometimes the action we’re going to take is going to make things worse.

Eric Zimmer 00:50:02  And in that way, this can be a way of of just holding that back a little bit.

Henry Shukman 00:50:07  Yes. That’s beautiful. I’m reminded of some of the recovery, you know, mottos and slogans like, I’ll never miss an opportunity to keep my mouth shut. And stay in my lane, you know. Yeah, I think I think that’s absolutely right very often. I mean, I tell you, this is one thing that was a big part of my early training in Zen, actually. I remember feeling like somehow, I mean, my life was a mess when I first got into this stuff. You know, I was really depressed, I was anxious, I was doing something that I was I was doing a PhD that was I didn’t want to be doing. And it was really sort of an enormous task. It was beyond me. And I also had really bad eczema that I’d had it right through my childhood, and it sort of came back and, you know, while I was at college and postgraduate and the moment I started meditating, I mean, almost to the day, you know, actually the first thing that happened was I slept a lot, an awful lot for a week, clearing off a kind of sleep debt.

Henry Shukman 00:51:12  but I could I could almost feel life subtly rearranging itself around me. That’s just because I was being still, you know, twice a day for a period of meditation. Gradually I started to see life more clearly. And I could see, man, this is not the right thing for me to be doing. You know, I need to get my emotionality under control and need to get more regulated. It just sort of subtle shifts compared to the obvious big elements in her life. They just started presenting themselves, either happening or needing to be brought about by me in generally in the way of just dialing things down, you know, and dining things back. And so that was a kind of discovery. I would never have named it. I mean, I did, you know, at that time I didn’t even know the term wu Wei. And even if somebody said, hey, you’re getting a little bit of familiarity with effortless effort, I said, what are you talking about? I don’t know what that means.

Henry Shukman 00:52:16  You know, but actually, I can see in reflection it was getting a little more open to that. It was it was coming to a place where it’s not so much the doing that sorts things out. It’s actually a reorientation, you know, Within that changes attitudes, that changes perspective. And then what? What one does then do is actually more efficacious and beneficial.

Eric Zimmer 00:52:51  Beautiful. Beautiful. We’re near the end of time. But what I’d love for you to do, for us now, is talk about effortless effort in the context of meditation. And maybe if you want to reference the way your app, but because I think this is another of those paradoxes that we sit with, like we show up at meditation for some kind of reason. We want to do our best with it. And as you as we’ve sort of explored, sometimes that grasping at the thing chases it away. So how can we apply this woo way to our meditation practice?

Henry Shukman 00:53:31  Yeah, thanks. It’s a great it’s a great question.

Henry Shukman 00:53:34  It’s kind of at the heart of what meditation might be all about, you know? So, I’ll speak a little bit to about the way, actually, because it’s very relevant here. You know, we, we, we were finding in our research before we built this app that of course, we know, you know, millions of people want to meditate, millions of people try. And whatever the number of millions is that have tried, it’s a much smaller number that actually stick with it in a consistent way. And one thing we also found was that a lot of people were finding that the meditation apps were overwhelming in their choice. Yeah, they have tons of micro courses you can do. And how do I know which one I’m supposed to do? You know, some of them have an introductory course and then they throw you, throw you out to find your way through a huge library of content at different teachers. Different. Yeah, different topics, you know, different courses and so on. So we said let’s just let’s just strip away any choice.

Henry Shukman 00:54:37  We’re just going to make it really easy. You don’t have to choose. We’re going to guide you. And the principle of that was kind of taking out the effort of choosing. Yeah. You’re just going to show up. You know, the effort is that you will show up. The effortless is you don’t have to choose. Yeah. And so it’s some you know. So there’s a top there’s a word here that I brought it up earlier I think that is relevant, which is that little piece of surrender. Yeah. That a little piece of trust. I mean, trust and surrender are almost two sides of a coin. You know, I say, okay, okay, okay.

Eric Zimmer 00:55:20  The thing it makes me think of is a phrase that I’ve always loved, which is that structure can liberate, structure liberates, right. That structure. We think of it as confining, but in many, many ways it’s liberating and I think that’s what your app offers. It’s the same thing I would get if I went on a if I go on a week long Zen retreat, a session, right.

Eric Zimmer 00:55:40  One of the things that is great about it for me is if when I to the extent that I can, I just relax into the form. I don’t have to decide anything. I just do that. You’re supposed to do this, then you do this, then you do this, then you do that. And I’m not saying that’s what I would want for my entire life to have all my choices made for me. But in certain areas, it’s a lovely thing to just have those choices make. And I think this is one of them.

Henry Shukman 00:56:09  Yes. Thank you. That’s that’s exactly right. I could totally, totally resonate with the sesshin experience, those Zen retreats where. Yeah, every minute basically, you know, you just surrender to it and it carries you if you just surrender. So this is a little bit like that in slow motion, stretched out by, you know, little activity day by day. It’s also, It’s also the, you know, that you can leave it to us, so to speak, to, to have set out a path that’s going to take you through all the primary things that you can.

Henry Shukman 00:56:45  You really it’s best to know and have some familiarity with and have some. Yeah. Skill with in a meditation training. You know, one of the things is that there’s a lot of a lot of these there’s a lot of different traditions and, and typically they’re strong in a certain area, those traditions, you know, but actually there are several key areas that I believe you need to practice in meditation, or at least have some awareness of and openness to in order to have it be maximally helpful in your life. And I’ve trained primarily for sure in Zen, but also in Theravada and and in modern mindfulness and and Transcendental meditation. Some advisor as well. So I kind of I, I feel that I’ve got a fairly well rounded grounding in the possibilities. And so we lead you through a sort of a program really that is introducing it a different concepts, different skills, different experiences. So you’re going to get, you know, by by by releasing into the program, you know, letting it take you, you know, you will be cultivating that ground we talked about at the start for sure.

Henry Shukman 00:58:05  And you’ll also be inviting certain openness to fertilization, you know, unexpected ways. And the woo way is letting that happen, you know, doing it, but you let it happen.

Eric Zimmer 00:58:18  Yep. And I think, you know, shows like the one you feed, provide a service to the world. Obviously, I love what I do, and I do it for a reason. and we make certain things more difficult. And one of the things that shows, like the one you feed in, the fact that there’s a lot of other ones just like it, is that you can be exposed to every spiritual, psychological, philosophical tradition under the sun. Lovely. Except when it comes to having a path to follow, in which case you can get very confused. I get myself confused. It’s why I years ago decided to to really focus in on Zen because I was just like, well, I’m going to do this. I could do that. Why should I do this? What I just lost. You know, and so having a path I think is enormously, enormously valuable.

Eric Zimmer 00:59:08  And your app does that. We’re at the end of our time for this session. We’re going to have another conversation. And in that conversation, I want to come back to the way, because despite having been meditating for 30 years, taken all kinds of meditation courses, I. a couple of weeks into your app had I was you said something that I had never heard said in this way and it opened a big door for me. So in the next conversation, we’re going to talk about what that door is. but for now, Henry, thank you so much. It’s always a pleasure.

Henry Shukman 00:59:44  Eric, I’m just thrilled. Delighted and honored to to get this time with you. Thank you so much.

Eric Zimmer 00:59:50  Thank you so much for listening to the show. If you found this conversation helpful, inspiring, or thought provoking, I’d love for you to share it with a friend. Share it from one person to another is the lifeblood of what we do. We don’t have a big budget, and I’m certainly not a celebrity.

Eric Zimmer 01:00:07  But we have something even better. And that’s you just hit the share button on your podcast app, or send a quick text with the episode link to someone who might enjoy it. Your support means the world, and together we can spread wisdom. One episode at a time. Thank you for being part of the one You Feed community.

Filed Under: Featured, Podcast Episode

Navigating Fear and Hope: the Everyday Courage That Shapes Our Lives with Ryan Holiday

May 30, 2025 Leave a Comment

Navigating Fear and Hope
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In this episode, Ryan Holiday explores navigating fear and hope and the everyday courage that shapes our lives. He unpacks how to confront our fears and how we need to do so, over and over. With great stories and insights, we are reminded that we don’t have to be fearless, we just have to begin.

Key Takeaways:

  • The concept of courage and its significance in everyday life.
  • The relationship between courage and fear, including how to confront fears.
  • The importance of personal agency and making choices that shape our lives.
  • The role of vulnerability in fostering connection and understanding.
  • Historical and contemporary examples of courage and heroism.
  • The four cardinal virtues: courage, temperance, justice, and wisdom.
  • The idea that courage is not just for heroes but is present in daily decisions.
  • The impact of sharing struggles and experiences on personal and collective healing.
  • The notion that hope requires courage, especially in the face of adversity.
  • The importance of taking action and making decisions to overcome analysis paralysis.

Ryan Holiday is one of the world’s bestselling living philosophers. His books, including The Obstacle Is the Way, Ego Is the Enemy, The Daily Stoic, and the #1 New York Times bestseller Stillness Is the Key, appear in more than forty languages and have sold over 10 million copies. He lives outside Austin with his wife and two boys … and a small herd of cows and donkeys and goats. His bookstore, The Painted Porch, sits on historic Main Street in Bastrop, Texas. His latest book is Courage is Calling

Ryan Holiday:  Website | Instagram

If you enjoyed this conversation with Ryan Holiday, check out these other episodes:

Why Community and Courage Matter More Than Ever with Laura McKowen

How to Overcome Cynicism and Embrace Hope with Jamil Zaki


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Episode Transcript:

Automatically Transcribed With Podsqueeze

Ryan Holiday 00:00:00  Really what courage is, is the idea that I can change things, whether it’s this tiny situation or it’s some globally complex situation.

Chris Forbes 00:00:17  Welcome to the one you feed. Throughout time, great thinkers have recognized the importance of the thoughts we have. Quotes like garbage in, garbage out or you are what you think ring true. And yet, for many of us, our thoughts don’t strengthen or empower us. We tend toward negativity, self-pity, jealousy, or fear. We see what we don’t have instead of what we do. We think things that hold us back and dampen our spirit. But it’s not just about thinking our actions matter. It takes conscious, consistent, and creative effort to make a life worth living. This podcast is about how other people keep themselves moving in the right direction, how they feed their good wolf.

Eric Zimmer 00:01:02  Every day we stand at a crossroads. One path is comfort. The other is courage. But courage isn’t just for heroes on battlefields. It’s in boardrooms, classrooms and kitchen tables. It’s the decision to speak up, to start over.

Eric Zimmer 00:01:20  To keep hoping. My guest today is Ryan Holiday, author of Courage Is Calling and one of the most influential voices in modern stoicism. We talk about fear, how to confront it, and how to act bravely not just once, but over and over. From the Stoics to Steinbeck, from whistleblowers to warriors. Ryan brings stories and insights that remind us you don’t have to be fearless. You just have to begin. I’m Erik Zimmer, and this is the one you feed. Hi, Ryan. Welcome to the show.

Ryan Holiday 00:01:54  Yeah, thanks for having me.

Eric Zimmer 00:01:55  It is a pleasure to have you on. We are going to be discussing your latest book in a moment, but let’s start like we always do with the parable. There’s a grandfather who’s talking with his grandson, and he says, in life there are two wolves inside of us that are always at battle. One is a good wolf, which represents things like kindness and bravery and love, and the other is a bad wolf, which represents things like greed and hatred and fear.

Eric Zimmer 00:02:20  And the grandson stops, thinks about it for a second, and he looks up at his grandfather and he says, well, grandfather. Which one wins? And the grandfather says, the one you feed. So I’d like to start off by asking you what that parable means to you and your life. And in the work that you do.

Ryan Holiday 00:02:35  Yeah. That’s interesting. I talk about this in a couple different of my books. There’s a wonderful quote from Martin Luther King where he says that there’s a North and a South in all of us, meaning, you know, sort of a good and an evil, and that these sort of forces are always at a kind of civil war with each other. And I think this idea that we have a higher self and a lower self. There’s the part of us that knows what’s right and the part of us that doesn’t do what’s right. You know, the sort of part of us that is good habits and the part of us this bad habits. And the idea that you’re ever going to sort of perfectly be one or the other is probably unlikely.

Ryan Holiday 00:03:14  But I do think you give one more power than the other, which to me is sort of what that parable is about. You know, sort of day to day, which one has more control, who’s winning sort of more often than not is kind of how I think about it that pertains, you know, to the idea in the new book, Two of Courage. I don’t think courage is this thing that you sort of magically, perpetually are. It’s something that sort of day in and day out, situation by situation. You either choose or don’t choose. And the fact that you’ve chosen it before doesn’t mean that you’ll keep it forever. And the fact that you’ve screwed up and fallen short in the past also doesn’t mean that you can’t make a better choice now.

Eric Zimmer 00:03:59  Yeah, in your books in general, I see a lot of you looking at historical figures as ways of really seeing how other people have stayed with the analogy fed their good wolf to to sort of remind us, because I think, you know, it seems like there’s two parts to this.

Eric Zimmer 00:04:17  One is even orienting to what does that mean? What does it mean to feed my good wolf? Or what does it mean to live a good life or a life of virtue? Then there’s the actually doing it.

Ryan Holiday 00:04:26  Yeah. Although I would also point out that I do try to look also at examples of where the Bad Wolf has won out. Again, to further the analogy. I try to do both inspiring stories and cautionary tales. Yeah. The idea being, we can sort of learn from the experiences of others, the costs and the benefits of those decisions, and that they might stick with us when we are faced with choices or temptations or difficult situations. I think we tend to learn by story. We certainly remember stories, and they sort of help us explain what we’re going through in the present moment. So I tend to look, as you said, for stories that sort of remind us either of what we’re capable of, positive or negative, and what the potential consequences of that could be either way.

Eric Zimmer 00:05:14  Yep. So we’re going to get into your book in more detail. It’s called Courage is Calling. Fortune favors the brave. But before we go deep into courage, I’m going to ask you to sort of set it up because this is the first in a four part series. Yes, of different virtues. So say a little bit about what the different virtues are and why did you choose them.

Ryan Holiday 00:05:35  So in both ancient philosophy as well as in Christianity. And then we see some similar renderings of it in eastern philosophy as well. There’s this idea of the four cardinal virtues. Cardinal doesn’t actually have a religious connotation. It comes from the Latin word caritas, which means hinge. But the idea that there’s sort of four pivotal virtues that the good life depends on, and those four virtues in Stoicism and Christianity are courage, temperance, justice, and wisdom. So this book is the first book in a series on those four virtues, courage being, I think, if not the most important, virtue, certainly the virtue that all the other virtues require almost from the outset.

Ryan Holiday 00:06:19  Okay. I can give you a quick definition of courage, or a quick definition of justice, or a quick definition of wisdom or temperance. But what does that actually look like in the real world? How does one apply it? How have people applied it, and how might we learn from them that that’s sort of what I’m trying to do in this book, as I do with all the other books. I usually pick a theme, as you said, and then sort of illustrate it with stories that are memorable and inspiring and, and sort of allow us to get into the particulars of. Okay. When you mean courage, you mean not show fear. No, it’s more complicated than that. So we’re trying to explore what courage looks like in reality.

Eric Zimmer 00:06:55  And I’m going to ask you to define courage in a minute. But I want to start where you end the book to a certain degree, which is with basically the end of one of my favorite books of all time, which is East of Eden by John Steinbeck, which I’ve read every couple of years for, I don’t know, 30 years now.

Eric Zimmer 00:07:15  And so I was wondering if you could just, you know, share with us kind of what you how you end the book around sort of the pivotal idea that ends East of Eden.

Ryan Holiday 00:07:26  Yeah. So at the end of East of Eden and actually Steinbeck talks about this at length. He has this wonderful book called The Journal of a novel, where he’s he’s sort of writing to himself as he’s working on the novel, and you see him sort of struggling with these themes, but he ends up talking to his editor about this, but he has this sort of breakthrough that the commandments are not, thou shalt not. Which sounds like you’re not allowed to do these things. And he says, actually the rendering is closer to. Thou may not or thou should not. Right. Meaning that we have a choice. And that the choice is everything in the choice is as you said, if you only had one wolf inside you. And it was the good wolf for the bad wolf. Well, then you wouldn’t really have any responsibility or accountability for who you were.

Ryan Holiday 00:08:18  Day to day, if you were a good person. That would be great, but it wouldn’t be really much of a credit to you because you were simply born that way. If you were a bad person, you really couldn’t be held accountable for that either, because it’s not your fault. It’d be like being short or tall. It’s not on you. It’s not a reflection of you. And so this idea that we have the individual choice, the basis of free will to choose to follow the ideas, to choose virtue, to choose which wolf we feed is, in fact, everything. I close the book with that story, but I open the book with a similar story that has no religious connotation, which is the so-called choice of Hercules. Hercules is said to come to a crossroads at either side of the crossroads. There are two goddesses. One goddess is the goddess of virtue. One is the goddess of vice. Vice says, look, you can have everything you want. It’s going to be fun.

Ryan Holiday 00:09:12  It’s going to be easy. It’s going to be wonderful. You’ll never have to care about anything again. And then the virtue, the goddess of virtue, says, I can’t make that promise. She says, it’s going to be hard. It’s going to be sacrifice. It’s going to be difficulty. It’s going to challenge you. But she says it will make you great. It won’t be easy, but the challenge will be everything. And so this choice that Hercules makes is obviously said to be the sort of founding of his mythological greatness. And so the idea that we have this choice, that it’s up to us, to me, is the essence of what we’re talking about.

Eric Zimmer 00:09:48  Yeah, I couldn’t agree more. So let’s go into courage. Talk a little bit about to start. How do you define courage?

Ryan Holiday 00:09:55  Well, I struggled with this at the beginning because there’s said to be two types of courage. There’s moral courage and there’s physical courage. And then it’s like, do I want to focus on physical courage or moral courage? What’s more interesting? How do they pertain to each other? How are they different? And then I really as I thought about it more and more, I realized that, well, what do they have in common? What are their similarities? What’s their connection? And I realized that at the core, all forms of courage are about risk.

Ryan Holiday 00:10:23  It’s basically, did you put your ass on the line? Like, did you physically step up and run into a burning building? Did you, you know, follow orders under fire? That would be physical courage, of course. But what is a whistleblower? What is a truth teller? You know, what is an artist who pushes the boundaries of what we accept. Well, why do we admire that? Why does that count as courage? They’re not risking their lives, of course, but they’re risking their livelihood. They’re risking their reputation. They’re risking being looked at strangely or criticized. So, you know, they’re still putting their ass on the line. They might not die, but they could die of some form of social death. And so the idea at the core of courage, to me, is the willingness to risk and to put yourself out there.

Eric Zimmer 00:11:16  Yeah. You say that courage is the management of and the triumph over fear. It’s the decision in a moment of peril or day in and day out, to take ownership, to assert agency over a situation, over yourself, over the fate that someone else has resigned themselves to.

Eric Zimmer 00:11:32  I just love that idea. And the other thing you say, I think is so important around this is that inherent in this is the belief that an individual can make a difference.

Ryan Holiday 00:11:40  Yes. You know, we talk about this idea. It’s sort of now fallen out of fashion, the great man of history theory. And I don’t think it’s fallen out of fashion because it’s sexist. It’s the idea that, like, an individual can change the course of human history. There’s, first off, a certain amount of courage just in that belief. But it’s easier to sort of look at the idea that it’s all hopeless, that it’s all complicated, that it’s all too big for an individual to possibly affect. And so I think really what courage is, is the idea that I can change things, whether it’s this tiny situation or some globally complex situation. There’s a great expression. One again, these are all little sexists. So I’m not the coiner of the phrases, but there’s another one that’s like one man with courage makes a majority, meaning that almost all things start as a person who is alone.

Ryan Holiday 00:12:34  But it’s through their courage, it’s through their commitments, through the actions that they take because of that courage that they are able to make that thing a reality. They bring people to them where they bring people along with them. That’s what courage is about.

Eric Zimmer 00:12:51  The way you’ve structured the book is you start off by really talking about what gets in the way of courage for most of us, which is fear. So let’s take a step or two back, at least as far as the order of the book, and talk about what are some of the things that get in our way as far as fear?

Ryan Holiday 00:13:10  Yeah. So fear gets in the way. But what is fear? Fear is a bunch of specific fears, right? Fear of what other people will think. Fear of the consequences. Fear of standing out. Fear of looking stupid. Right? Fear of any number of things. But I think the irony is, often it’s not even those things we’re afraid of. We just have this vague fear, right? This sort of undescribed, unspecified, vague sense that it’s not worth it.

Ryan Holiday 00:13:40  Or it’ll be hard or it’ll be difficult. And so when we think of fear, I think one of the first things we want to do is just like, well, what am I actually afraid of here? Right. You know, you’re jumping off a high dove. What are you afraid of? Well, you’re probably afraid of dying, right? Well, like, let’s actually think about whether that’s physically possible here. That doesn’t mean it’s magically going to be easy, but you can sort of logically get to a place where, you know, okay, the fear I have is irrational. So if I push past it, I’ll be fine. Now it’s really just a matter of do I have the willpower to push past it? I think about this when I dropped out of college. You know, I was really scared. It was like I was 19 years old. I had no life experience. I had no sense of how the world actually worked. So I was afraid, basically, that if this didn’t work out, I would end up under a bridge somewhere, right? Like, I was afraid that by leaving college, I was cutting the only safety net that possibly existed between me and homelessness.

Ryan Holiday 00:14:45  Right? Which was, of course, fundamentally irrational. And so it was really helpful to have someone in my life. I had a mentor who was like, Ryan. I got sick for a year in college. I remember he told me this. He’s like, I got sick for a year in college. I had to take a year off, and I was in the hospital the entire time. And he was like, do you know how often this has ever come up in my life since that? I was gone for a year of college. It took five years instead of four years. He’s like, it’s literally not once come up, he’s like, this happens all the time. People leave and they have to come back. People leave and they never come back. But he’s like, it’s not what you think it is. It’s not as irrevocable as your fears are telling you that it is. And it was like, oh, okay, that makes sense. So then I decided to do it and that was the other part.

Ryan Holiday 00:15:30  So I went and did it. I remember I walked into the registrar’s office and I said something like, you know, I’m here to drop out of college and they were like, that’s not even one of the options. They’re like. You can take a semester off, but your credits are good for ten years. And so this thing that I’ve been so afraid of, actually, I had a ten year like, undo button that I could press at any time. And so it’s really important that one that we break things down. And then the benefit of breaking them down and proceeding, whether it’s jumping off a high average, dropping out of college, is now the next time there was one of those decisions in my life, I was much more savvy and aware that it wasn’t as scary as I thought it would be, and that there’s almost always a way out.

Eric Zimmer 00:16:20  Yeah, that’s so good. I was just working on recording a short cast thing for Blinkist this morning, and we were talking about that exact point of like, hey, get specific about your fears.

Eric Zimmer 00:16:30  Like, really move out of the vagueness. You know, like, everybody will think I’m an idiot. And it’s is more like, well, there’ll be three people there, so three people will think I’m an idiot, right? Like, you know, get specific.

Ryan Holiday 00:16:41  And how many of them are even paying attention and give a shit, right? And so you’re, you realize like, often you’re like imposter syndrome, right? That’s a real fear a lot of people have. Well, what if they really investigate and they find out that I’m not as good as I think or whatever? And it’s like they’re not thinking about you at all. They don’t care, you know, like they are consumed with their own problems. Your obsession with yourself is making you think this is a bigger deal than it actually is.

Eric Zimmer 00:17:08  Totally, totally. Yeah. And then that second part of that that you said really is like, okay, well, if my fear comes true, how will I respond? I love the word.

Eric Zimmer 00:17:17  It’s not irrevocable. And I think that’s so important is to recognize, like, I mean, some decisions are irrevocable, but the vast majority of them are not. And you can change. I mean, when I left my full time job to start doing this podcast and the coaching and stuff full time, you know, I just had to spend a little bit of time and think, well, if this doesn’t work, here’s the 13 different fallback plans I could have. Right. The risk. Am I taking a risk? Sure. But like to your point, it’s not like this either works or I’m homeless. It’s like, well, this either works or I get another job. Like, it’s not the end of the world.

Ryan Holiday 00:17:51  Yes. There’s consequences. Right. We’re not saying like, don’t be afraid. There’s zero consequences. There’s consequences. But it’s the vagueness, the indescribable ness of those consequences that makes them loom much larger than they actually are. There’s a story I tell in the book about Ulysses S Grant.

Ryan Holiday 00:18:10  This goes to your point about, you know, sort of how many people are watching. He’s crossing the plains of Texas as a young soldier, and he hears these wolves like, and he thinks it’s like hundreds of wolves. He thinks they’re about to be devoured by this rabid pack of wolves to go to. The idea of this show and the guy he’s with is a tad more experienced, and he says something like, you know, Grant, how many wolves do you think there are? And Grant doesn’t want to sound like a like a wuss. And so he says, I don’t know, 20. And he was like, that was like half what I actually thought there were. You know, he thought there were so many rules. The guy here is, is he just sort of smiles. They finally come upon the wolves and there’s two of them. There’s two wolves. And what he realizes is and he says, I never forgot this for the rest of my political and military life. He said, there’s always fewer of them when they are counted.

Ryan Holiday 00:18:58  Right. So you take your fears, you take your risks. You think about the worst case scenario. Then you actually go like, okay, I’m going to inspect this. I’m going to like really look at it. You know, you’re like, well, I don’t want to say this. I might piss people off. And your idea of people is like a stadium, right? Or like but there’s actually like 15 of them, right? I think about this every time I say something that’s maybe a little political or a little controversial. You’re like, oh, people aren’t going to like this, but like people, it turns out to be like seven weirdos. Who sends you poorly, you know, poorly written emails that make you go like, how is this person reading my stuff anyway? I’m not sure they’re literate, right? Like, you realize that, like the people that you were worried about, you actually don’t care about and are far fewer in number than you would have if you had had to guess they’re actually were totally.

Eric Zimmer 00:19:56  I mean, I work with a lot of people who are trying to build their business and step out online a little bit, and they’re just like, I’m just worried that I’m going to get all these people hating on me. I said, no, no, no. Your biggest worry in the beginning is that nobody is going to pay any attention to what you’re doing. You don’t have to worry about the haters for a while, right? And then to your point, in seven and a half years of doing this, the number of people who’ve said anything to me, that’s really awful. I mean, it’s just so few.

Ryan Holiday 00:20:23  Yeah. And so what we often do is we make these things bigger than they actually are, so then we don’t have to do them right. If you’re like, well, I don’t want to piss people off, so I’m not going to do it or I don’t want to be laughed at, then we don’t have to do it right. It’s like the excuse to not put yourself out there.

Ryan Holiday 00:20:40  You’re looking for someone to give you permission to not do it.

Eric Zimmer 00:20:43  Yeah. There’s something you said near the end of the section on fear that I loved, and I’m just going to read it because I think it speaks to a different kind of fear. That’s really important, though. But you said we’re afraid to open up. We’re scared to share. We don’t want anyone to know how we’re feeling inside. And so all of us feel more alone. You know what pain is caused by the inability or the unwillingness to sort of share our difficulties, our fear, you know, the things that are going on inside us. And I just loved that idea of, you know, when we don’t do that, more of us feel alone.

Ryan Holiday 00:21:17  Yeah. Because I’m specifically talking about stoicism, which, you know, is a philosophy that a lot of people associate with having no emotions. That’s sort of the big stereotype of stoicism. In fact, that’s like what the word stoic means in English. Like the sort of lowercase stoic means like emotionless, invulnerable robot.

Ryan Holiday 00:21:41  And so I wanted to talk specifically about that, that like, hey, courage is not just, you know, charging into the fray under fire. Courage is also saying, like, you think about the soldier who does do that, right? But then the soldier who comes home and has trouble adjusting, or maybe they’re addicted to something, or maybe they’re depressed, or maybe they’re even contemplating suicide. I wanted to talk about the courage to say, hey, I’m struggling. I’m having a hard time. I need help because this is almost a scarier thing for brave people to do, right, to put yourself out there in that way. And so the idea of being vulnerable, as Brené Brown talks about this much better than I do. But the idea of being vulnerable is often the scariest thing in the world for people.

Eric Zimmer 00:22:58  It’s interesting. I’ve shared this before. Back when I had years and years and years in sort of a corporate world, although a lot of them were startups. But, you know, it was still sort of a business world.

Eric Zimmer 00:23:08  But the more that I sort of shared who I was, I shared my addiction history, I shared my depression issues, you know, the things that happened in my life, not in a like I’m talking about me all the time way, but just was a little bit more open about that. It was amazing. Over the years, the number of people that would come back to me and then say, oh, you know, this is going on because all of a sudden it was safe. Or to use your word, they’re not alone. Yeah. They recognize like, oh, okay, other people feel this way and it’s okay to talk about it here.

Ryan Holiday 00:23:38  We talked about this. Right. So it’s like, let’s say everyone’s scared of doing something. Maybe it’s a political stand. It’s standing up to a bully. You know, it’s, responding to an emergency. One man with courage makes a majority, right? One person says, no, we have to do something, and then they go do it.

Ryan Holiday 00:23:54  And the other one says, yeah, they’re right. Let’s go do something. But this is also true for mental health issues. This is also true for emotions. This is also true for doubts about something. Right. So the person who says, hey, I am having trouble with this. Like you think about what the MeToo movement actually was, right? It starts as women on Facebook saying, hey, something like this happens to me too, right? So put aside some of the political implications of the movement, put aside excesses or problems or cases that you agree with or disagree with the idea of women saying, hey, I was afraid to talk about this, but now that other people are are open to talking about it, I’m going to say, me too. That’s what the power of Courage is really about. And again, this is such important moral courage. First off, there’s an element of physical courage that we probably shouldn’t under state as well. But this is the decision to talk about a thing that why weren’t they talking about it before? It was uncomfortable.

Ryan Holiday 00:24:59  They thought they would be judged for it. They thought there might be professional consequences for it. They thought they might get a reputation because of it. Right. So the decision to put your ass on the line and say, screw all of that, it’s important for me to say this. It makes a difference for me to say this. I’ve been inspired by the other people who said it, and I am going to say something that is courage and it helps not just yourself, but other people.

Eric Zimmer 00:25:25  Yeah, that’s a beautiful example of it. So let’s now move into the courage section of the book. And the book is set up in that fear section, the courage section. And there’s there’s little essays under them. Yeah. You know, lots of different ones that tell stories from history and make points. So I thought I’d just grab a couple of them out of there and let you, let you talk about them. And then maybe you could pick 1 or 2 that you most want to talk about.

Eric Zimmer 00:25:51  But one of them that I liked was just start somewhere. Do something.

Ryan Holiday 00:25:56  Yeah. You know, I’m actually going through this right now. I’m working on this other book, and I’m struggling a little bit. It was going well, and then I got distracted and it’s anyways trying to remember that. Does it have to be perfect, particularly the first draft? I have to be willing for parts of it not to be good, and I just have to start. If I sit around and I wait for it to be easy. It’ll never happen if I wait for the perfect opening or opportunity. It’s never going to happen. If I want what I’m doing now to be as good as what I’ve done before, what I did even earlier on this project, again, I’m going to be sort of stymied or stuck. So I just have to start. And so today I was like, you know what? What’s the littlest thing that I could work on? I was like, you know what? I’ve got all this sort of loose research that I haven’t found a place for.

Ryan Holiday 00:26:43  I’m just going to start organizing that and hopefully that will sort of knock something loose, which it did. Yesterday was sort of a mediocre day. Today was kind of a mediocre day. But tomorrow I now suddenly, because I did this work, have pretty clear marching orders for what I need to work on tomorrow. So just start somewhere. You don’t have to magically do some huge, heroic, impressive thing. You just have to make a little bit of progress.

Eric Zimmer 00:27:12  I don’t want to divert the conversation too far from the topic of your book, but I’ve got to ask a question about how do you organize all your research? Because you are really good at pulling lots of different pieces together. And I am always fascinated by the authors that do that really well, how they organize it.

Ryan Holiday 00:27:34  So for me, I’m always reading these are books behind me, and as I’m reading, I’m like, okay. For instance, I’m writing a chapter on Churchill and is somewhat reckless financial habits. That’s what I was thinking about.

Ryan Holiday 00:27:44  So this is a book I read called No More Champagne about Churchill and his finances. And then these are all the pages that I’ve marked that I thought were interesting. And then I usually record them on notecards, and then the note cards are usually the building blocks of the book. So I have a big box, all the different, as you said, the book’s three parts. Then there’s chapters in each part. Those notecards get slotted in in their respective parts, and those are the building blocks for each specific chapter in each book.

Eric Zimmer 00:28:15  Makes total sense. So you’re doing it sort of paper based. Old fashioned way?

Ryan Holiday 00:28:20  Yes, definitely. And it’s not a perfect system. There’s like a thing I know I wrote down and it has a guy’s name on it. A baseball player that I want to write about, and I can’t find it. And I don’t know how I’m possibly going to find it. So it’s not a perfect system, but for the most part, it gives me everything that I need.

Eric Zimmer 00:28:37  Makes sense. Okay. Thank you for that. I just was fascinated to know. So back on to courage. A couple of these we’ve already hit. We’ve talked about how courage is contagious. You know, how one person being courageous spread. So that was one I was going to hit. We kind of talked a little bit about preparation makes you brave. so let’s move on to be the decider.

Ryan Holiday 00:28:58  Okay. The thing that’s scariest is making a decision, right? As long as you don’t decide, it can be anything. It can be everything. You won’t be held accountable. Right. The decision is when we pull the trigger and that that holds us back. So I was just, you know, just really talking about the power and the courage required to make decisions. Because if you don’t decide, sure, things will stay sort of in one spot, but by definition, you’re also not going to be making progress. It’s easy to endlessly debate things. It’s easy to endlessly research and consider them.

Ryan Holiday 00:29:39  It’s easy to ask for unlimited amounts of advice, but at some point you got to pull the trigger. You got to go. And that’s what that chapter is about.

Eric Zimmer 00:29:50  Yeah, you quote an expression in there that I think is great, which is whatever. You’re not changing, you’re choosing. It’s corollary is, you know, not making a decision. Is it kind of a decision unto itself. But I actually like this phrase better. What you’re not changing. You’re choosing which is really good. And then I can’t remember what was in the book or something else you wrote. I think you led me to it, but it was a a William James quote. There is no more miserable human being than the one in whom nothing is habitual but indecision. So true. Having been there, I know how miserable that is.

Ryan Holiday 00:30:24  Yeah, to me that’s the importance and the power of routine. That’s the importance and power of sort of setting your ground rules. And for those who don’t do that, they face every day as an endless stream of unlimited decisions.

Eric Zimmer 00:30:41  Totally. I mean, with coaching clients, one of the first things we’ll work on is we have got to decide ahead of time, yes, what we’re doing. Because if you don’t, as you just said, you will spend a lot of your precious energy trying to figure out, well, when am I going to do it? What should I do? When am I going to do it so that when it comes time to do it, you already have sucked out half your resources or more, and thus it’s really hard to do when you know exactly what you’re doing, when then you could take all that energy and just sort of channel it, like do it.

Ryan Holiday 00:31:12  Totally. Yes, if you set the rules for yourself. And this is kind of where the virtues come in to play. Also, if you’re like, hey, I’m a person who defaults towards courage, then when a scary situation comes up, you’re like, this is what I do, this is who I am. If you’re like, I don’t really know what I believe.

Ryan Holiday 00:31:30  I don’t really know what I stand for. I don’t really know what’s important to me. Then you’re also winging it. And that’s when you go, but this will cost me money. but this could be hard, right? But, this seems fun, right? And so setting the sort of rules for yourself help you in those stressful, difficult situations.

Eric Zimmer 00:31:48  A lot of your work is about values, you know, what are the values that we have? Do you have any particular ways that you like of sort of determining personal values and getting clearer on what they are? There’s a lot of different systems out there. There’s a lot of ways to do it, but I’m just kind of curious, as somebody who’s pretty firmly ensconced in thinking about values, if you have any thoughts on, you know, for people who are like, well, I’m not really sure what my values are.

Ryan Holiday 00:32:15  I mean, what I love about stoicism in particular, and I brought up earlier that sort of stoicism and Christianity are aligned on these four virtues.

Ryan Holiday 00:32:22  What I like about the stoic case for those virtues is there’s no sort of metaphysical, supernatural explanation for them. I’m not faulting anyone who chooses it, but if you don’t believe that the idea is divine, it’s like, well, sort of, why should I do it right? So Christianity always has this sort of benefit of like, well, this is what God says, right? And stoicism, I think, is making the argument not, hey, if you live in opposition to the four virtues, you will go to hell. I think the Stoics are arguing your life will be held right. Your life will suck. You might be rich, you might be powerful, you might be famous. But that will bring you very little joy, very little happiness, very little meaning. And in fact, probably bring you the opposite of those things. Right? And so that’s really what I love about stoicism. It’s making sort of a logical, self-interested case for virtue and value.

Eric Zimmer 00:33:16  Now, are these four virtues that you talked about courage, temperance, justice and wisdom.

Eric Zimmer 00:33:21  Are those considered sort of the four core ones, you know? Is that sort of throughout stoicism or certain Stoics or. I’m just kind of curious how ensconced those four are, and then how many branches off of those four? Perhaps there are.

Ryan Holiday 00:33:35  Those are the core fundamental values of stoicism. And I think you would argue that every other thing that the Stoics talk about or believe could be ascribed to one of those virtues. So. So someone goes, well, what about love? Is that a virtue? And it’s like, yes, it is. But love, I think, fits under justice how you treat people, your connections to other people, so on and so forth. So I think those four virtues are all encompassing as far as values go. And it’s also important to remember that the four virtues don’t work in isolation from each other. So courage in pursuit of injustice to the Stoics is not impressive. In fact, it’s, you know, a vice, not a virtue. And wisdom is the virtue that helps us discover when and where the other virtues apply.

Ryan Holiday 00:34:25  Right? So these virtues can be configured in an unlimited amount of combinations that can give you clarity or guidance in each and every situation.

Eric Zimmer 00:34:58  Before we dive back into the conversation, let me ask you something. What’s one thing that has been holding you back lately? You know that it’s there. You’ve tried to push past it, but somehow it keeps getting in the way. You’re not alone in this, and I’ve identified six major saboteurs of self control things like autopilot behavior, self-doubt, emotional escapism that quietly derail our best intentions. But here’s the good news you can outsmart them. And I’ve put together a free guide to help you spot these hidden obstacles and give you simple, actionable strategies that you can use to regain control. Download the free guide now. At one, you feed a book and take the first step towards getting back on track. A question that I’ve seen posed a couple times that I thought was an interesting question, and I’ve got kind of my thoughts on it, but I’m curious what yours were.

Eric Zimmer 00:35:54  Is that from a surface level? Buddhism and stoicism seem to have a lot in common. There’s a lot of overlap there. I’m curious if you have a sense of where you think there might be differences?

Ryan Holiday 00:36:06  Yeah, that’s a good question. I mean, I think what I particularly love about stoicism is its engagement in the world, where I tend to find with Buddhism, and both in the Buddhist texts, there is kind of a disengagement from the world. To me, the image of the Buddhist is the monk, and the image to me of the stoic is like the emperor or the general, or the person in the midst of the busy world. Like stoicism is founded in the Athenian Agora, the busiest marketplace in Athens. That’s not where I associate. I mean, there were Buddhist samurai. And Confucius, for instance, is a political advisor. So in the eastern tradition, there’s certainly some level of engagement. But I do think I see stoicism much more a philosophy of the world of the self, as opposed to so much of the detachment that we sometimes see in the eastern texts.

Eric Zimmer 00:37:03  Yeah, that makes sense. I would agree, and I think a lot of what’s happening in Western Buddhism is I think there’s a lot of correction oriented around that idea, where actually I think that’s not what is necessarily in a lot of the Buddhist core teachings. But you’re right, there is an idea of of withdrawing from the world. But there certainly is also a lot of talk about compassion and action. And I think that’s one of the things that Western Buddhism is doing right, I think is is correcting for some of that and saying, look, yeah, these things are great to develop this wisdom and this capacity for reflection and all that. But to what end? You know, not a metaphysical idea that like, oh, well, if I awaken all being simultaneously awakened, like know like is the wisdom that I’m developing, the compassion I’m developing, is it showing up in the world in a useful way?

Ryan Holiday 00:37:56  Yeah. Seneca was talking about the Epicureans, not the Buddhist, but I think it’s a similar point.

Ryan Holiday 00:38:02  You know, he says the difference between the Stoics and the Epicureans is that the Epicurean says, I will not be involved in public life unless it’s unavoidable. And then the stoic says, I will be involved in public life unless it is impossible. Right. And I think that’s a distinction the stoic defaults to. I’m a philosopher. Plus I am a insert profession, important public role, etc. and I sort of tend to see the Buddhist as the. Well, I’m a I’m a philosopher. And yes, occasionally you have to do x, y and z.

Eric Zimmer 00:38:41  Yep. So let’s move back to the book and I want to hit on the idea. The last part of the book is around heroism and talk about the difference between, say, heroism and courage.

Ryan Holiday 00:38:58  So obviously fear holds us back. Courage is therefore rare. But there is something beyond courage. One of the examples I’ve come to explain this is that there’s like Michael Jordan walking away from professional basketball at the height of his greatness. Took immense courage.

Ryan Holiday 00:39:16  Would have been scary. It was real cost to it. Lots of people told him it was a bad idea. He had to go be bad at baseball in front of millions of people. He had to go from being the greatest to like a minor league baseball player, right? That took incredible courage. Now, is that heroic? Well, probably not. I mean, it doesn’t really help anyone. It doesn’t, like, make the world a better place. Same with Michael Jordan on that sort of flu game. Comes back from the flu. It’s courageous. Takes immense amount of endurance. You know, it’s not like solving world hunger or something, right? I contrast that with Maya Moore, who I think two, almost three seasons ago now walks away from, you know, an equally dominant career in the WNBA to work full time at freeing a man wrongly convicted, who was sentenced to life in prison. So the courage to walk away for oneself takes courage. The decision to walk away for something greater than oneself is heroic.

Ryan Holiday 00:40:19  And so what we decide to commit to, what our courage is in service of, is the sort of next and ultimate sort of level to think about and consider.

Eric Zimmer 00:40:31  Yeah. You say courage is not an independent. Good heroes have a reason. And you also say the difference between raw courage and heroic lies in the who. Who is it for? It’s a beautiful idea. So what are some of your favorite things you’d like to share around? Heroism. I’ve got a few here, but I’m going to let you lead for a second.

Ryan Holiday 00:40:50  Well, I open that part of the book with the story of the 300 Spartans at Thermopylae. And, you know, obviously it’s made for some great movies, but it’s also, I just think, one of the most indelible examples of selflessness and sacrifice in the history of Western civilization. These 300 Spartans. There was more because they were supported by some auxiliary troops. But basically, like a few thousand Greek soldiers went out and fought a Persian army that may have numbered as many as 1 million.

Ryan Holiday 00:41:22  And they did it, obviously knowing they would lose. I mean, nobody marches out against those kind of odds, convinced, like, oh, we’re really going to win this thing, right? So why did they go? Because they knew that this sort of shaky Greek alliance needed time to come together. There were people who thought the Persian threat was overstated. They thought it didn’t matter. They thought like, you know, we were better off handling this individually. And these 300 Spartans go out and make the ultimate sacrifice to bind these nations together to make a statement to show, first off, that it’s possible for the Greeks to fight and do real damage, but that a unified Greece is the only viable option. And, you know, you just read about these 300 guys. Every single one of them had children. And in fact, that was the point. The 300 Spartans were chosen specifically because they had children, because they believed that they wouldn’t let those children down, and that they were also protecting the younger soldiers who hadn’t had time to start families yet.

Ryan Holiday 00:42:32  So it’s just this, you know, magnificent story of human greatness, I feel of in this brief moment, they become more than just 300 people. They become legends, you know, they become transcendent.

Eric Zimmer 00:42:46  Yeah. In one of the sections called Going Beyond the Call, you talk about the Spartans again and you say the the opposite of fear, the true virtue Contrasted with that vice was not fearlessness. The opposite of fear is love. Love for one another. Love for ideas. Love for your country. Love for the vulnerable and the weak. Love for the next generation. Love for all. And you’re saying like that’s what was really underlying. What they did was love.

Ryan Holiday 00:43:12  It obviously wasn’t for their benefit that they were going out to fight this battle, because they weren’t coming home, and they knew that it was a selfless gift. For other people, I think about as America withdrew from Afghanistan, you think of these 12 servicemen and women who walked out for days on end into these crowds to load people up onto airplanes knowing that, you know, something could go wrong at any moment.

Ryan Holiday 00:43:39  And tragically, it did. And 12 of them lost their lives, but they also, in the process, were integral participants in one of the greatest humanitarian rescue efforts in human history. and they are not the recipients of the benefits of that risk. So. You know, if I decide to write a book that’s transgressive, there’s a danger to that. But if it succeeds, you know, I reap the rewards of that, right? Financially, reputationally, etc.. When you look at sort of truly heroic people, what makes it so impressive is that there was no real hope for them, at least of the benefits of that sacrifice.

Eric Zimmer 00:44:26  You tell a story in the section about The Audacity of Hope, about John Lewis. Do you want to share that one?

Ryan Holiday 00:44:33  That’s another one. I mean, you think about what John Lewis goes through in his life. I think he’s arrested 50 times. He’s beaten more than 50 times. He’s nearly killed several occasions. If there was ever a person who had reasonable justification for giving up on human beings, giving up on white people.

Ryan Holiday 00:44:54  Just giving up on people in general. It was John Lewis and yet who sort of continually was there with hope and forgiveness and optimism and commitment to change belief that change was possible. You think about, in a weird way, the courage that it takes to remain hopeful when people are showing you time and time again that they’re probably not worthy of that kind of belief. To be a black American in 1950 or 1960, and to believe that America was decent and good and would eventually, inevitably make progress in these areas. I mean, there was not a lot of evidence for that, right? I mean, there’s that expression when people show you who they are, believe them. Like we were showing over and over and over again, like sort of who we were. And so to have a belief, to have hope, to have the belief in yourself that you could actually affect change and make that real. I mean, that’s just one of the most magnificent things I could possibly imagine.

Eric Zimmer 00:46:06  Yeah, you say just about one of the craziest, bravest things you can do in this damned world of ours is to keep hoping, because there are so many reasons not to.

Eric Zimmer 00:46:14  That is so true. It is seems like such a, on one hand, crazy thing to do, but so critically important.

Ryan Holiday 00:46:22  Yeah, I mean, we’re not talking about sort of vague hope. Oh, this will take care of itself, right? This isn’t like, oh, I don’t need to do anything. It’ll work out. That’s not how it goes. But it’s the courage to believe that one has the ability to make a difference, to push the ball forward in some way. And I think also that on a long enough timeline, progress can be made.

Eric Zimmer 00:46:42  Yeah, I think it’s that holding those two ideas at the same time. Right. Like, yeah, things are really messed up. There’s all kinds of problems and it can get better. It’s really seen both of those. If you only see one of those, you either end up hopeless or you end up naively optimistic. But when you hold both of them, that’s a constructive and practical realism.

Ryan Holiday 00:47:04  Yeah. There’s a James Baldwin quote that I love.

Ryan Holiday 00:47:06  I’m pretty sure it’s in the book. He says not everything that’s faced can be changed, but nothing can be changed unless it is faced. Right. So sticking your head in the sand, pretending everything’s fine. Being afraid to look at it or deal with it. Obviously that keeps things the way that they are. That’s not to say that just because you’re brave enough to say, I’m going to try to do this, that the bill will pass, that the company will succeed, that the person will, you know, be willing to hear what you’re saying and, you know, go to rehab or, or whatever. But if you’re not willing to try, it’s definitely not going to happen.

Eric Zimmer 00:47:45  Yeah, I think that’s very spot on. Let’s end with you just sharing a little bit about your bookstore. You opened a bookstore right as the pandemic opened, and I’d be curious to hear a little bit about that story, but I’d be also curious to hear how has it been going? Say, since you’ve sort of talked about that in a couple different places.

Eric Zimmer 00:48:06  I’m kind of curious. The latest update, but for people who don’t have the first update, why don’t you give us that part?

Ryan Holiday 00:48:11  Well, it’s actually worse than you said, because I was I had just started the process. I had just paid for the location for which I was hoping to open a bookstore at the beginning of the pandemic. So then, you know, looking at things in the cold light of March 2020 and April 2020 and May 2020, as it literally looked like the world was falling apart and it wasn’t even possible to be open as a bookstore, right? My wife and I had to sort of sit there and go, are we sure we want to do this? Did we just light our life savings on fire? You know, but we stuck with it. We took our time. We really thought about what we wanted to do, why we wanted to do it, why we thought it was important and we pushed through. It opened in earlier this year and actually, so far it’s doing great.

Ryan Holiday 00:48:57  I mean, you never know with these things, but I think now, like, what if I had, you know, thrown in the towel in March? What if I’d cut my losses? It might have been cheaper in some ways. But when I watch people walk through the bookstore, as I did before I came up here to record this, it’s like, oh, this is what’s on the other side of those decision points. When you go to, I want to do the easy thing. Do I want to do the hard thing? Do I want to push through? Do I want to quit? I don’t think that I could have thought that what it is now and how it’s doing was possible, and I only found out that it was possible by pushing through, by trying. As they say, all growth is a leap in the dark. You have to take that leap. No guarantee it’ll work. It might blow up in your face, or it could surprise you and be even better than you thought.

Eric Zimmer 00:49:42  Yeah. So right now it’s going well then?

Ryan Holiday 00:49:44  Yes. fingers crossed. But yeah, it’s going great. And it was cool to like, launch, you know, my new book through my own bookstore.

Eric Zimmer 00:49:50  I was gonna say to you, did you throw yourself a book launch party at your own bookstore?

Ryan Holiday 00:49:55  No, no, no parties because of the pandemic. But, you know, instead of saying, hey, go buy this book from Amazon, which, of course, I also want people to do. I said, you know, buy this book from my bookstore or just like, hey, we can put my book in the window as a new release. You know, like, how cool is that? So yeah, there’s just been a whole other element to it that’s been really fun.

Eric Zimmer 00:50:17  Before we wrap up, I want you to think about this. Have you ever ended the day feeling like your choices didn’t quite match the person you wanted to be? Maybe it was autopilot mode or self-doubt that made it harder to stick to your goals.

Eric Zimmer 00:50:32  And that’s exactly why I created the Six Saboteurs of Self Control. It’s a free guide to help you recognize the hidden patterns that hold you back and give you simple, effective strategies to break through them. If you’re ready to take back control and start making lasting changes. Download your copy now at one you feed. Let’s make those shifts happen. Starting today when you feed. As someone who has paid attention to the work you’ve done over a few years, I know how deeply you love books you’re reading lists. I always love to get and see, and so I’m happy you’ve got a bookstore that’s really wonderful.

Ryan Holiday 00:51:14  Thank you. Yeah, it’s called The Painted Porch. It’s in this little town called Bastrop, Texas, right outside Austin. And the other thing I think about it just for other people, I’m not saying you should start a bookstore, but if you become successful, if you, you know, have achieved whatever you’ve set out to achieve, if that’s not allowing you to then go do things you’ve always wanted to do, sort of what’s the point, you know? And so I think the cool part about the bookstore is I love books, I love bookstores.

Ryan Holiday 00:51:42  And if I can’t do this now, what sort of is the point of the other things? Right? And so that’s sort of something that’s kind of empowered me along the way.

Eric Zimmer 00:51:51  Yeah. Well, Ryan, thank you so much for coming on the show. I hope the book does great. I hope the bookstore does well and I hope to someday visit it. I need to get down to Austin to visit my brother who lives there. So I’ll come by.

Ryan Holiday 00:52:03  Please do. That would be awesome.

Eric Zimmer 00:52:04  Thanks so much. Appreciate it. Thank you so much for listening to the show. If you found this conversation helpful, inspiring, or thought provoking, I’d love for you to share it with a friend. Sharing from one person to another is the lifeblood of what we do. We don’t have a big budget, and I’m certainly not a celebrity, but we have something even better. And that’s you just hit the share button on your podcast app, or send a quick text with the episode link to someone who might enjoy it.Your support means the world, and together we can spread wisdom. One episode at a time. Thank you for being part of the One You Feed community.

Filed Under: Featured, Podcast Episode

Failure as Fertilizer: Learning to Bloom Again with Debbie Millman

May 27, 2025 Leave a Comment

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In this episode, Debbie Millman explores how we can use failure as fertilizer and learn to bloom again. Debbie’s book and this conversation is about more than just gardening tips or tools, it’s about what happens when we let ourselves be bad at something, especially later in life. Debbie opens up about learning to grow and why failure might be the richest soil we have. Whether you’ve ever felt stuck, afraid to try, or unsure if it’s too late to start.

Key Takeaways:

  • Personal growth and development through gardening
  • Lessons learned from failure and embracing new experiences
  • The metaphor of gardening as a reflection of personal growth
  • The impact of the COVID-19 pandemic on personal endeavors
  • The importance of understanding circumstances that affect growth
  • The balance between effort and environmental conditions in achieving success
  • The significance of being a beginner and confronting fears later in life
  • The role of external support and accountability in personal challenges
  • The interplay between creativity, self-worth, and professional obligations
  • The connection between nature, personal experiences, and emotional well-being

Debbie Millman was named “one of the most creative people in business” by Fast Company, “one of the most influential designers working today” by GDUSA, and a “Woman of Influence” by
Success magazine. She is also an author, educator, designer, and podcast
pioneer. Debbie is the host of the Webby and Signal award-winning podcast Design
Matters, one of the first and longest running podcasts in the world; Chair of the first-ever
Masters in Branding Program at the School of Visual Arts, Editorial Director of
PrintMag.com, and the author of eight books. Debbie is the recipient of a Cooper Hewitt
National Design Award and a Lifetime Achievement award from AIGA, the Professional
Association for Design. She is currently a Harvard Business School Executive Fellow.

Debbie Millman:  Website | Instagram | LinkedIn

If you enjoyed this conversation with Debbie Millman, check out these other episodes:

Fluke or Fate? Embracing Uncertainty to Live a Fuller Life with Brian Klaas

How to Find Zest in Life with Dr. John Kaag

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Episode Transcript:

Eric Zimmer 00:01:12  It’s not every day that someone you think you know, someone urbane, accomplished, cerebral, shows up with mud on their boots and tears in their eyes from doing a pull up.  Debbie Millman, longtime host of Design Matters and acclaimed designer, returns to the show with a quiet surprise a book about gardening. But the garden isn’t about tips or tools. It’s about what happens when we let ourselves be bad at something, especially later in life. In this conversation, Debbie opens up about learning to grow and why failure might be the richest soil we have. Whether you’ve ever felt stuck, afraid to try, or unsure if it’s too late to start. This episode is for you. I’m Eric Zimmer. And this is the one you feed. Hi, Debbie. Welcome to the show.

Debbie Millman 00:02:03  Hi, Eric. Thank you for having me.

Eric Zimmer 00:02:05  I am excited to have you back on. We are going to be discussing your latest book, which is surprising to me about gardening, and we’ll talk about that in a second. But before we do, we’ll start in the way that we always do with the parable. In the parable, there’s a grandparent who’s talking with a grandchild, and they say, in life there are two wolves inside of us that are always at battle.

Eric Zimmer 00:02:27  One is a good wolf, which represents things like kindness and bravery and love, and the other is a bad wolf, which represents things like greed and hatred and fear. And the grandchild stops. Think about it for a second. They look up at their grandparent and they say, well, which one wins? And the grandparent says, the one you feed. So I’d like to start off by asking you what that parable means to you in your life and in the work that you do.

Debbie Millman 00:02:53  Well, as a designer, I think that we’re constantly in a mode of making very deliberate decisions about our work. Solving problems. Making choices about which direction to take. And I think that extends to every aspect of one’s life. I think that we don’t just design things, we design our choices and we design our paths. So the parable really dovetails quite seamlessly into, I think, what it means to be a designer.

Eric Zimmer 00:03:33  I’ve had you on the show before, and you very kindly had me on your show a number of years ago, and that day is carved into my memory as one of my favorite memories.

Eric Zimmer 00:03:45  Tell me why I was in New York City and you interviewed me. No, you’re a big part of it. You’re a big part of why I came to New York City. So I came to New York City and you interviewed me, and I believe I might have also appeared on Jonathan Fields show, but it was a whole day where I did things related to this podcast in its work, and at the time, I was still working a full time job in the software business. But it awakened this thing in me that was like, maybe someday this could be what I do, and now it is. But anyway, I just think back to that day. I remember coming to your studio and everything about it was wonderful. So I want to thank you for that day because I have a terrible memory. But that day really stands out to me. Thank you. That day also introduced me to you in person, at which time I thought, and this is similar to what you say in the book The Garden, about what your wife Roxann, thought about you, which was I was like, she is such a New Yorker, you know, sophisticated and design oriented, and all of these, like, New York type things.

Eric Zimmer 00:04:50  So I when I saw you had a book about a garden, had a little bit of a double take. I was like, oh, hang on a second, like, I’ve got you as this very urbane, sophisticated person. Not that gardeners aren’t sophisticated, but it just sort of surprised me. So when I was reading your book and you mentioned that your wife Roxann had the same reaction when you talked about gardening, it sort of tied all these memories together for me. So talk to me about why a gardening book now?

Debbie Millman 00:05:21  Well, it wasn’t something that I was seeking. but first let me just say thank you. Thank you for having me on the show again. Thank you for caring about my work. And thank you for sharing that memory, because it’s really wonderful. And I’m so glad that we have this connection. Me too. As far as why a gardening book now, it’s primarily because I was asked to write one.

Eric Zimmer 00:05:47  That’ll do it.

Debbie Millman 00:05:49  I was not in any way seeking about gardening, how to garden.

Debbie Millman 00:05:54  Anything about gardening? Honestly, I’ve always, as an adult, tried to cultivate some sort of greenery around me in the various apartments that I’ve lived in. Over the four decades I’ve been in Manhattan. But writing a book on gardening was not in my wheelhouse. Yeah. Yeah. It wasn’t on my bucket list. I had these various somewhat dubious attempts and results in the previous spaces that I tried to cultivate as some outdoor space gardening, and as I mentioned, various apartments since the 90s. But it wasn’t really until I came to Los Angeles during Covid that, no pun intended, that my efforts blossomed. Yeah. Roxann had gotten this house that I’m sitting in right now, two weeks before we started dating, and I had been living in Manhattan for all of my adult life. And so when we first met and started dating, we were long distance commuting to each other. And she has a beautiful house. The back yard when she first moved in was a very typical sort of suburban backyard. Beautiful, beautiful tree, a lot of grass.

Debbie Millman 00:07:11  Boxwoods boxwoods. And because I had always tried to cultivate some outdoor space in the various places that I’ve been living, when I first got here, I asked her if she would mind if I used it up a little bit, you know, with some potted plants and various herbs and things like that. There’s a beautiful garden center a couple of blocks away, so it was super easy, very convenient. And so that’s what I started doing. And it was very rudimentary because it was during Covid. Let me backtrack. Then when Covid hit the world, we decided that I would come to California because I had a lot more. time. We. We had sky. We had a car. It made more sense for us to be somewhere where we could get out a little bit. And so that’s what I did at the time. You know, we had no idea that the world was going to shut down for as long as it did. I remember the then president at the time saying, oh, we’ll be all back together for Easter.

Debbie Millman 00:08:15  And that was in March. And so I was like, oh, pack for two weeks and I’m sure everything will come back to normal after that. Well, we all know what happened after that. And so I need a lot more, I need a lot more underwear. And so we were here. I had a lot more time. I was working on a book at the time, but also had a lot of other time to do things and decided to expand my efforts in the garden as a way of trying to feel closer to the world. And I was having some luck because of the weather And so I started with the herbs, and then I went to lettuces. And then I got more ambitious and started to plant tomatoes and cucumbers and things that I really loved. And I was documenting that on Instagram, and I was making these little ten panel stories about what I was doing, but it was also very much about what was happening through the eyes of, of somebody. That was also, as the rest of the world was living through Covid and how gardening made me feel more hopeful and a bit more optimistic, and seeing how we could grow and evolve.

Debbie Millman 00:09:32  And the Ted folks who I have good relationship with through my podcast and through speaking there and so forth, reached out when the TEDx conference went completely online that year and asked if I could create some Interstitials between the online talks to break up the the talking and I made some stories about gardening. They asked me if I would make some visual essays that I would narrate and that would be shown throughout the conference. And so I made one about gardening. Fast forward to 2021, and for my 60th birthday, I had decided to take an expedition to Antarctica for two reasons one to see Antarctica, and then also to try and witness the total eclipse of the sun that was happening over Antarctica at the end of 2021. And it was a magnificent expedition, and it was everything I hoped it would be except for the eclipse, which I didn’t see because of cloud cover. And so I wrote all about that and also put it up on my Instagram. And somebody from a wonderful art director and editor saw it on Instagram, and she worked at a farm magazine and reached out and asked if I’d be interested in doing a piece for the magazine, which I did.

Debbie Millman 00:10:57  Fast forward another year as things happen and I get an email unsolicited from an editor at Timber Press, which is part of one of the Big five, Hachette, and she asked me if I’d be interested in doing a book on gardening. Having seen all of these visual stories that I had done, and I thought she was pranking me and like, I’m like a New Yorker, like I don’t write. I’m not a gardener. If you’re interested in my talking about my journey to try to be a gardener and the myriad failures along the way, and what I’ve learned and how I’ve grown and evolved and so forth. Then I’m all in. But if you’re expecting me to be the next Martha Stewart, you have the wrong girl. And so she wrote back and said, that sounds great. A quest to become better at gardening through the lens of visual storytelling would be welcome. And so that’s what I did.

Eric Zimmer 00:11:53  Yeah, and to say that it’s a book about gardening is to sort of describe it and also sort of not write, because there’s no real gardening advice in there unless you take like, move to California because it’s easier than New York to grow things like as advice, which you don’t even directly give.

Eric Zimmer 00:12:11  And like you, it’s a it’s a beautifully designed book that with very few words and not a whole lot of pictures, really conveys some beautiful things. Thank you. And I think it’s a lot like your design work in your podcast, which on the surface it’s sort of about the surface, right? And yet there’s a deep reservoir right underneath it of lots of depth and, and wisdom. And you kind of start off early on by saying that seeds are tiny and densely packed with their entire existence. What does it mean to exist? And you also sort of talk about how the universe itself sort of came out of this seed idea. And I think that’s a beautiful place to sort of start with this idea of something coming from not quite nothing.

Speaker 4 00:13:07  Right.

Eric Zimmer 00:13:08  But almost nothing.

Speaker 4 00:13:10  Yeah.

Eric Zimmer 00:13:11  Talk to me about how that, as an overall idea has been important to you throughout your life.

Debbie Millman 00:13:18  Well, as I was beginning to become more adept at gardening and was not just planting container plants and and things that I bought already born, so to speak, from nursery.

Debbie Millman 00:13:36  I was also planting seeds and to think that any plant, any vegetable, any tree starts from this sort of tiny, compact enclosure that then opens to create an entire universe of sorts is endlessly fascinating to me, and I’m somewhat obsessed, endlessly fascinated. I don’t know the right words here about how we all got here, and I think about it all the time, Eric. I think about it all the time. And in some ways it’s sort of depressing because I’m never going to know.

Speaker 4 00:14:21  We’re so far away.

Debbie Millman 00:14:23  As a species from understanding the mysteries of of how we got here and why we’re here and how it all started. And, you know, added the helium in the hydrogen. Get here in the first place. You know where the carbon come from. There’s so many questions that I have. And yeah, I’m on this quest of trying to understand my purpose here, and what my contribution can be and how I could potentially, if at all, make a difference. And so it all it all ties together the universe and the if we did get here from that, this big bang, this tiny, tiny, densely packed point then expanded to create what we are in such vastness that it’s inconceivable, it’s incomprehensible for us to even be able to envision.

Debbie Millman 00:15:18  Yep. What we’re a part of. And to think that, you know, trees have this grand underlying root system that communicates. And it’s all so beautiful and so abstract and so mysterious, and it all feels so mystical and magical in so many ways that It. For me, it became the ultimate way of trying to express the questions that I have and the tiny little answers that I tend to tell myself.

Eric Zimmer 00:15:56  One of the things that I really thought about a lot as I was reading the book is that you describe your early attempts at just buying plants and putting them outside and them dying and failing. And there’s two narratives, I think, that we we sometimes tend to separate about what doing anything successfully looks like. And one narrative is you just have to keep trying. You know, failure is just a chance to move on. You just if you just keep trying, you’ll succeed. And there’s truth in that. Absolutely right. I mean, you’ve talked about it a lot. There’s a lot of truth in it.

Eric Zimmer 00:16:37  And then at the same time, there’s another element that sometimes the story is, well, yeah, except it’s all about circumstance. And what I think is interesting about the gardening example is that you actually need to bring those two together. You can’t grow anything anywhere. You could keep trying and it’s not going to grow. Right. So it’s not all about just keep trying effort. And yet at the same time it is about iteration. It’s about learning. And it’s about saying, okay, if I want this thing to grow, whatever it is, whether it’s this plant, whether it’s my career, whether it’s my relationship, that there are circumstances, conditions that are more conducive to things growing. And I think that’s one of the big challenges that a lot of people wrestle with. It’s one of the I think the core tension is like, do I just keep going in this direction, or have I learned something that tells me, yes, keep going, but go in that direction. And I feel like your book somehow, to me, just brought that whole question into really clear focus.

Eric Zimmer 00:17:50  I don’t know what my question is now.

Debbie Millman 00:17:53  You sure do.

Eric Zimmer 00:17:56  That’s my reflection. I’ll let you go where you like with it.

Speaker 5 00:18:00  Well.

Debbie Millman 00:18:01  I write about how as I’ve gotten older, it’s a lot more difficult for me. Or it had been more difficult for me to attempt things that I’m not good at. And it’s a bit narcissistic in a way, in a lot of ways to think that if you try anything, you’re going to be good at it. Why should you be if you haven’t been taught, if you haven’t practiced, if you haven’t extended yourself into a realm that is further than what you’re currently aware of. And so asking for help has never been particularly easy for me. Asking for favors has not been particularly easy. And so the idea of trying to learn something new out of a school environment where that’s sort of the accepted norm. And it’s been a long time since I was in a desk, as opposed to behind a podium teaching. It took a while for me to realize that in order to, no pun intended or grow, that I had to ask for some guidance and that watching HGTV wasn’t going to be enough.

Debbie Millman 00:19:18  And so I really needed more deeper learning about the conditions that I was in. And this is a good metaphor for life, I think, and how to how to grow from there, how to get better at what I was attempting to do. And this experience actually helped me find the courage to begin to do other things that I’ve said for as long as I can remember that I really wanted to do, but for some reason had this obstacle path in front of me that felt too daunting to attempt. And it’s opened up that obstacle a little bit to make more attempts at doing things that I never really felt like I had the ability to do. And that’s been liberating in a lot of ways.

Eric Zimmer 00:20:12  Can you share what any of these new attempts have been? Well, you don’t have to if you don’t want to.

Speaker 5 00:20:17  But no, I’m fine with it.

Debbie Millman 00:20:18  I’m on day 481 of learning French on Duolingo.

Eric Zimmer 00:20:22  Nice.

Debbie Millman 00:20:24  You know, it comes a time where you’re like, I can’t keep saying, oh, I wish I knew how to speak another language.

Debbie Millman 00:20:30  I mean, yeah, you either do it or you don’t do it. I just it was tired of hearing myself wishing for this magical ability and thinking that somehow I’d learn it in my sleep. And so I’ve done this now for a year and a half, and I’m not very good. And I’m not a great learner, but I know a lot of words. Yep, yep. That’s been also revelatory. And then the other is getting into shape. And so I’ve been working with a trainer for two years. And so, you know, I’ve got a little bit of muscle happen.

Eric Zimmer 00:21:08  All right.

Debbie Millman 00:21:10  And so those two things are things that I never really envisioned that I’d be able to begin to do in the way that I’m doing it now. With consistency.

Eric Zimmer 00:21:22  I think that ability to do something and not be good at it and still do it is so sort of fundamental. And for some reason, for me, I think that it’s an ability that has gotten better in me as I’ve gotten older, where I think when I was young, I thought that how good I was at various individual things was some reflection on how good I was overall.

Eric Zimmer 00:21:47  And now I’ve realized, like whether I can roller skate or not says nothing at all about who I am as a person or my value. So if I go out and make a complete fool of myself, roller skating, which I assure you is what happens. I mean, the last time I went roller skating, they now have designed these things. They look like walkers on wheels, and I’m out there tottering around with one of them, which was, I mean, my younger self would never have gotten. Like, no way. My older self is like, well, this is kind of mildly humiliating, but I’m just going to keep doing it. But I think that maybe it’s certain things, like I decided early on I was going to be a musician, and I’m not musically talented.

Debbie Millman 00:22:31  Really?

Eric Zimmer 00:22:32  No, I’m not surprised.

Debbie Millman 00:22:34  I’m surprised.

Eric Zimmer 00:22:35  Yeah. I don’t know why I am. I am deeply not natural at it, but I love it deeply. But I’ve just stuck with it for, I don’t know, 35 years now.

Eric Zimmer 00:22:46  And I’m. I’m okay. You know, like my friend Chris is a natural. Like, I’ll spend three months figuring out and learning how to play something that he will then turn around and play in like an hour of time, which is mildly like, yeah, infuriating. And I’m like, you know what? That just doesn’t matter. Yeah, because I’m doing this thing because I love doing it. And I think that with your gardening is such a great example of you just embracing learning how to do something because you simply wanted to do it same way with French or with getting in shape.

Debbie Millman 00:23:20  Getting in shape has been the hardest one for me. Even harder than French I think, because I’m much more comfortable doing anything cerebral, and I’m also more comfortable learning anything on my own in that I can go at my own pace. I don’t have to worry about judgment. Yep. For lots and lots of reasons that we’ve talked about on on your podcast before. I for all of my life, have been very cut off from the physicality of living.

Debbie Millman 00:23:49  Yeah. And I always approach things from a much more cerebral point of view where I can think through things and not necessarily engage physically through things as much. Yeah. And so I was forced to start working with my trainer when I had surgery and needed to do PT, and that’s how I started my relationship with my trainer. He’s also a physical therapist. He’s a PhD in physical therapy, and I was very compliant with what I needed to do. The one physical activity that I did engage in on the daily was walking. I’m a native New Yorker and was always walking through the city and always walking wherever I could go because I enjoy it so much. And I didn’t want to give that up because that is my that was, at the time, my only physical activity besides pacing, you know. And so I started to feel better about myself physically and then decided that I should continue working with him in weight training and so forth. And so that’s what I’ve done. And I’ve even started running. People I tell they’re like, did aliens take over your body? It was.

Eric Zimmer 00:25:10  Yeah.

Debbie Millman 00:25:10  And I’m like, yes, they did a long time ago. Now I’m shooing them away.

Eric Zimmer 00:25:14  Right, right.

Debbie Millman 00:25:15  When I first started with him, because of all the trauma. If I couldn’t do something, Erik, I would start crying involuntarily. Like, it wasn’t like. Oh, boohoo. Poor me. This was involuntary projectile tears Here’s because I was facing so much of my own. I don’t even know what the word is. Bad wolf. You know.

Eric Zimmer 00:25:41  Yeah.

Debbie Millman 00:25:42  Yeah. And so the first time I did a pull up actually cried, but it was not because of my trauma. It was because of my joy that I could actually do something like that. Yeah. And again, it was involuntary. And that’s been one of the most surprising things in my life, actually, I have to say, to be able to be conscious in that way or even allow my subconscious to bubble up in the way that it has. Yeah, has done a lot to help me.

Eric Zimmer 00:26:42  It’s hard to separate natural affinity from avoidance responses sometimes.

Eric Zimmer 00:26:48  Yeah, right. So I think I do have a natural affinity towards the brain. I think that’s part of who I am. And I think I was very disembodied for a lot of my life. And so yeah, physicality is something that I’ve sort of learned and I also, paradoxically, have figured out that it is, for me, the most important mental emotional health tool I have. If you forced me to only have one the rest of my life, which I’m glad I don’t because I need like 27 of them. But if you force me to have one, I would probably say it’s exercise. Really, because there’s something about what it does for me, the way it connects me up inside the way it releases anxiety, the way that it increases energy. It’s just it is for me. Maybe my most important one again. I’m glad I don’t have to choose, but it’s been a really important one for me. And the thing about exercise that I always find fascinating, and listeners have heard me talk about this a lot, but I do find it really interesting is how if something we come to see as so valuable for me every time I’ve ever done it, when I’m done, I’m like, I’m glad I did that.

Eric Zimmer 00:28:02  Like literally every time. Why does it remain hard? You’d think basic reward learning would have me running to the treadmill every day, but I don’t. And I think it’s just because it’s it’s such a significant output of energy that as organisms, we are designed to evaluate that amount of output very closely. You just don’t, you know, you just don’t go running around for no good reason as an organism trying to survive. But I still remain kind of fascinated by that. That dynamic of how I faced it today, I was like, I know I really the best thing for me to do would be to get on the peloton and ride. That’s really hard. So what I’ve learned to do is I just went like, well, okay, you’re preparing for Debbie. Instead of sitting in front of a screen reading, put in your headphones and just at least go walk outside in the sun while you prepare, you know? So those little sort of hacks. Yeah. Help.

Debbie Millman 00:28:58  That’s why I have to keep working with the trainer, Eric, because I’m too weak and lazy to do it on my own.

Debbie Millman 00:29:05  You know, David Foster Wallace talks about what a real leader is in Consider The Lobster, his collection of essays, and he talks about how a real leader is somebody who helps people who are weak and lazy to do things that they would not consider doing on their own. I’m paraphrasing. Yep. But we can weak and lazy were in that I’m not paraphrasing those words and that’s what my trainer does for me. He helps me get over my weakness and my laziness to do better things that I can do on my own. And if I don’t have an appointment with him, I don’t do it. And I’m hoping that I can get to a point where I can. The one area where I think I might is actually with running now, and I don’t know that I’ll ever be a runner. Maybe, maybe I’ll be able to do A5K1 day. But I experienced that runner’s high one time once and that was like, wow. Yeah. I never felt something like that before, but I totally hear you. It’s not like I’m going rah rah, time to run.

Debbie Millman 00:30:21  I mean, I haven’t run since the last time I had a training, session and I’ve been on a book tour, so you can only imagine what that’s been like. Yeah, and I do find it super interesting, this whole idea that you just brought up, because I don’t have any issue starting to make a drawing. I have no issue engaging in anything I really love. Yeah, on my own. I don’t need a trainer to draw. I don’t need a trainer to read. I don’t need a trainer to write. I need an editor. But I don’t need anybody to motivate me. So I do find that I have to think about that a lot. That’s a really, really interesting observation that I need to mull. Yeah. And if you do find the solution to that, please let me know.

Eric Zimmer 00:31:02  Well, for me, the solution has been accepting that like that. That’s normal. Right. That it’s just okay that like making myself do something very physical is always going to take a certain degree of coercion, right? I told you before the call, I just got done writing this book.

Eric Zimmer 00:31:17  I turned it into the publisher about a month ago, and a bunch of the book is about how we actually change. And one of the things that I’d picked up through years of doing the show, but also really got driven home as I did a lot more research for this book is that if you gathered all the behavior change scientists together in the world and you put them in a room. Right. I think the thing they would all agree on is that relying on our own internal engine, what we would commonly call willpower, is generally a bad idea for anything. That is, for whatever reason, for us, difficult to do.

Debbie Millman 00:32:00  Why is that?

Eric Zimmer 00:32:01   Because our environments matter so much, and willpower is a very finicky thing because it’s tied somewhat to mood, right? Because if we think about motivation or willpower in the sense that most of us know it, it has to do with how much we feel like doing something. And if you’ve got a mood system like mine, it is just up and it’s down and it’s up.

Eric Zimmer 00:32:27  There are some people who are a whole lot. Probably like, you know, steady or up at like 80%. I feel good 80% of the time. And for them might be a little bit different. But for people whose mood system is as variable is most people, you can’t rely on just that. So it becomes all about what are the strategies that you, as an individual, need to figure out that will get you across the start line for whatever that thing is? So there may be people listening to this or like, I don’t have a problem going running. I just get up and I just go running. But when I think about sitting down to do something creative, oh my God, it’s like a total block comes up.

Debbie Millman 00:33:06  Okay.

Eric Zimmer 00:33:07  And I would say they’re not lazy. You’re not lazy. It’s different in what we find easy to do. So for you you need to set up a structure. And a trainer is a very wise structure. It’s why fitness classes exist, because people are like, oh, if I sign up to go to the class, I’m more likely to go.

Eric Zimmer 00:33:25  And if I actually go, then I’m more likely to work hard. It’s just it’s wisdom, right? To know, like, oh, I need support, I need help, I need these structures. Whereas for somebody different, they might need to sign up for an art class to do it because they just won’t do it because for them the friction is high related to previous failure or doubts that they’re good at it. And so for all of us, I think that change to me, I always think of just as like a puzzle, like, what are the puzzle pieces that I need to put together that make this thing work and for you? With exercise, you finally got the puzzle pieces lined up, and they’ll probably get underlined again at some point. And you’ll need to go, oh, let me think. Okay. What what pieces do I need to put in here?

Debbie Millman 00:34:09  I think it also has a lot to do with who’s teaching you.

Eric Zimmer 00:34:11  Yes.

Debbie Millman 00:34:12  And I think that part of what has made me feel capable or emotionally available to do this is my trainer.

Debbie Millman 00:34:24  You know, he’s so lovely. He’s so patient. He really. I was very clear with him when I started. I’m like, look, I have all these issues. And so I hope that you can be respectful of them. And I have a lot of limitations. And blah, blah, blah, blah blah. And he was like okay. He’s been super respectful always. But he’s also unwilling to let my own limitations, my own self perceived limitations impact my actual abilities. Yep. And I’m not talking about abilities to do any physical activity. I’m talking about my mental health.

Eric Zimmer 00:35:09  Your mental. Before we dive back into the conversation, let me ask you something. What’s one thing that has been holding you back lately? You know that it’s there. You’ve tried to push past it, but somehow it keeps getting in the way. You’re not alone in this. And I’ve identified six major saboteurs of self control. Things like autopilot behavior, self-doubt, emotional escapism that quietly derail our best intentions. But here’s the good news you can outsmart them.

Eric Zimmer 00:35:40  And I’ve put together a free guide to help you spot these hidden obstacles and give you simple, actionable strategies that you can use to regain control. Download the free guide now at one uEFI book and take the first step towards getting back on track. My partner Jenny, who you met when I came to New York. She’s a similar to you in physical things when we met. You know, it’s been almost 11 years ago. At this point, probably she just hated everything that had to do with exercise and movement. It was something she was like, I know I need to do it and I hate it, you know? And she could find periods where she made herself do it. And over time, she has learned, I think, just to appreciate it more. But I remember we took I was like, I really want to learn to play tennis. Like, why don’t we go take tennis lessons together? And the first two tennis lessons, similar to you, ended in tears with her. There was just something about a ball flying at her that just brought up.

Eric Zimmer 00:36:39  Like being scared as a child and like, I hate this. Yeah. You know, and and just the inability to know what to do. And just so I think some of that stuff is really real for us. And again, I think that people face this in different ways. I mean, I know people all the time were like, I really wish I could learn to play guitar. And I’m like, well, of course you can, you know? But you have to be really, really uncomfortable for a while in doing it right, because you’re going to be terrible at it for a little while. I mean, everybody’s terrible at guitar to start. Just because you can’t make those shapes with your fingers, your fingers just aren’t strong enough. But any learning to do anything. And so I think when we look at that and we’re like, okay, there’s this thing that I want to do and I’m having a really hard time doing it. To me is just about okay. What? You know, what’s the strategy that we can come up with? And you sort of snuck in the back door of it by having to have a trainer for your back that also then managed to shepherd you through another door.

Debbie Millman 00:37:33  Right?

Eric Zimmer 00:37:33  Yeah. Which is amazing.

Debbie Millman 00:37:34  I love how you’re helping me better understand myself in this podcast.

Speaker 6 00:37:43  It’s fantastic.

Eric Zimmer 00:37:44  So speaking of podcasts, when I was getting into and preparing for this interview, something happened that as I was doing and I was like, that is amazing. And it is this you have been doing your podcast. You are at the point I am at now. I’ve been doing this podcast a decade. So when I started this podcast, you had already been doing it for a decade before that. And everybody’s always to me like, well, you’re one of the early founders. I’m like, no, not exactly, but holy mackerel, 20 years. Does that fill you with pride. What? How do you feel when you think about 20 years of having these conversations?

Debbie Millman 00:38:23  It makes me very humbled about the nature of time, because that went by in flash.

Eric Zimmer 00:38:31  Yeah.

Debbie Millman 00:38:32  And I remember my first podcast, I was interviewing John Fullbrook, who was then the art director at Simon and Schuster, and I was super nervous.

Debbie Millman 00:38:42  I had my notes in front of me, but I also had, because he’s a book designer, a book jacket designer. I had covers of his books all pasted over my office walls so that I could easily refer to something. I chose John not only because he’s a fantastic designer and a good friend, but because he’s extremely gregarious. And I felt like if I choked, which was a really good possibility he could carry on with. Yep. Thankfully I think I’ve grown in the 20 years but it’s surreal Eric. It’s surreal. And it’s also surreal to see how both AI and the show have evolved and what it means to again, coming back to this pun that I don’t really intend but to to really grow as anything. Yeah. I didn’t grow up thinking I want to be a podcaster when I grow up. There was no such thing. And that this very unusual path that my life took, based on a cold call from an internet radio network. Please edit that out. Like, what if I hadn’t picked up that call?

Eric Zimmer 00:40:03  Isn’t that fascinating?

Debbie Millman 00:40:05  It’s.

Eric Zimmer 00:40:05  I interviewed a guy recently. His name is Brian. I think you say it Klos. And he wrote a book called fluke, and it is a on many levels. Do you know the book or.

Debbie Millman 00:40:14  Yeah, I’m going to read it. It’s a great, great title.

Eric Zimmer 00:40:17  Yeah, it’s all about how life is like you just described. Like. Yeah, you don’t answer that phone. Your whole life is different. You know, he talks about how the city of Kyoto was originally on the slate to be bombed by the US, and it turned out that the war director of the US had gone to Kyoto about 20 years before on a vacation and loved it. So he said, no, let’s not do that one. Like it’s crazy. Like that is life. When you look at it, there’s just all these things that I could have just decided not to do. X and my whole life would look different. And his point is ultimately that if you embrace that, how little we actually control and how little actually happens, like, you know, for a reason that it can be freeing and liberating.

Eric Zimmer 00:41:09  It’s also deeply disconcerting on on some level, too, I think.

Debbie Millman 00:41:13  Yeah. I mean, it takes both the good and the bad things. And puts them in a completely different. You see them through a different lens. And I think that’s also something to honor.

Eric Zimmer 00:41:25  Yeah. It goes a little bit back to what we were talking about earlier with gardening. Right. Like there’s both what you do which matters, what you do matters. And there’s all the elements that you can’t control about growing anything. You can be more strategic, like you cannot plant roses like you once tried to do in a fully shady patio that that’s plant a fern there. Right? There’s strategy. And ultimately, though, you control what you can, but there’s a certain element of it that is just out of your control. You can’t make something grow.

Debbie Millman 00:42:03  That’s for sure. You don’t control nature. Not in the slightest. nature is much bigger and stronger and more capable, and that is a very liberating realization. You can do your best.

Debbie Millman 00:42:17  You can try your best. You can try to provide the best possible conditions, and you have to just leave it at the door.

Eric Zimmer 00:42:48  Another point of intersection with you and I a little bit is that your wife? Roxanne and I both did a project with a company called Rebind II, where you pair a person like Roxanne with a book. She did Age of Innocence. I did the Daodejing and mine is about to come out. I think hers has probably been out for a little while. The Dao is all about that idea of you just have to work with the way nature is, if you try and go against it, you’re going to lose every time.

Debbie Millman 00:43:17  I had a plant that had died and it had been really established. And then over the years, in a previous home that I lived in, and I talked a little bit about this in the book, the rhododendrons in my previous home. And I was devastated to watch them die and wanted to pull them out of the ground after they had died.

Debbie Millman 00:43:40  And it was really hard. I felt like I was fighting with nature. You know, it didn’t want to come out of the ground. And if pulling a plant out of the ground is fierce, you know, so is everything else.

Eric Zimmer 00:43:57  Yeah. I don’t know if you said this in a book itself or elsewhere, but I put it under the notes I have for the book, which is failure is fertilizer. It feeds the next attempt, the deeper insight, the unexpected path. And I love that idea because it doesn’t just say, just again, this idea that we mostly talk about with failures, try, try, try again. But I think that the wisdom there is. Yes. Try again. But as you point, like maybe there needs to be a deeper insight before you try again. Maybe there needs to be a different path. You actually have to be learning. It’s not just keep trying.

Debbie Millman 00:44:34  Right. And I think that it’s really important to be conscious about your failures and not just keep trying.

Debbie Millman 00:44:47  Because if you keep trying to do something the same way without understanding what led to the failure and what you can do to improve the odds of success. I don’t know why anything would be different if you just keep trying in the same way.

Eric Zimmer 00:45:04  Yeah, I think it’s one of those really difficult things about people who are trying to build anything. I’m thinking of it in a business sense, having been in the startup world for a lot of my life. But it’s really hard to know. It’s like, do I just need to keep going in this direction? Because it just takes time and people are slowly coming on? Or is this the wrong idea, the wrong direction? When do I pivot? How have you thought about that in your life? Like, do you have any way of sort of thinking through that, whether as a designer or in any way?

Debbie Millman 00:45:35  I think it depends on who you’re doing things for.

Eric Zimmer 00:45:38  Okay.

Debbie Millman 00:45:39  And the bar that you need to be able to reach in order to do something.

Debbie Millman 00:45:47  If you’re doing something for someone else and you’re getting paid to do it, there’s much less tolerance for failure. And that could include your shareholders. It could include a board. It could include, clients. If you’re doing something for yourself, I think you have a bit more leeway. For example, when I started the podcast, I was working a full time job. I was working as a as a corporate executive, and I was making a good salary, so I wasn’t dependent on this other effort that was really started as a labor of love. I didn’t need to monetize it. I didn’t need to do anything other than really fulfill my own creative dreams and hopes and aspirations. And to a large degree, it’s still the case for me. I’m lucky that I can monetize it in some ways, but I’ve never been dependent on it. And when you take out the dependency equation, it gives you a lot more freedom to experiment or evolve in ways that don’t impact others. If you’re being hired to make something for something else, or for the public or for profit, it does change the way in which I think you approach anything and ever so slowly.

Debbie Millman 00:47:15  You know, now that I’m in my sixth decade, I’ve tried to eliminate the need to fulfill any obligation to the outcome for others purposes. And it’s taken a long time, and I’m very lucky and privileged that I’m in a place right now where I can do that more frequently. Yeah, but that’s also a choice. You know, I’m not as comfortable anymore fulfilling financial obligations. I don’t want to live a life anymore where I’m working to increase the market share of of products that I don’t feel proud of doing. And and I did that for a very long time. Not that I wasn’t proud of them. I mean, I, I am very proud of the work that I’ve done. I just don’t feel the need to redesign any more fast food restaurants, or over-the-counter pharmaceuticals or soft drinks or salty snacks. And again, I’m very lucky that I was very successful doing that. But there comes a time where you have to decide how much more of this work do I want to do in service of that work? And so I feel extremely privileged to be able to take the talents that I manifested and grew and developed over my corporate career, and now applied them to movements and efforts that I feel are helping the world be a little bit safer or a little bit kinder.

Debbie Millman 00:48:48  And that’s the work that I’m trying to dedicate myself to doing now.

Eric Zimmer 00:48:52  Yeah, it’s a really tricky thing. I mean, we started this conversation with me sharing this magical day in New York City, coming to your studio and me being like, God, I wish I could do this full time. And now I get to do it full time. And that comes with a shadow side to it, which is that this thing that started just because I wanted to do it and loved doing it, now provides a living for me and for a couple other people. And so it’s different. And I think for me, the thing that I have to sort of continually sort of do is like, yes, I have to hold that there. It’s it’s real, it’s true. It needs to be. And I also need to turn as much of my attention as I can to what about this matters to me most deeply. And that actually is then what ends up creating the best work. But it’s always a mixed thing.

Eric Zimmer 00:49:45  I wanted to ask you about your career you talk a lot about, and you’ve advised a lot of young people about their careers, and it’s easy to look at your career, maybe many people’s careers, but I can look at your career and I can see it. Okay. It started, you know, down over here to the left. And today it’s up over here to the right in that all the things you just described are true. Like, you are better able to do the work that you want to do. You’ve had some degree of financial success. So if I look at it I go, okay, look. Start it down here to the left. Ends up here to the right. Straight line up. That’s not it. Right. So I was wondering if you would share a little bit about some of the times that you might have felt like, okay, my career was going well, and now all of a sudden it feels like, oh, you know, or any sort of bumps in the road or different things that sort of give us a little bit more of the nature of the up and down that happens in that chart if we zoom in on it.

Debbie Millman 00:50:45  Yeah. I mean, I don’t know anything that is just a straight line up. I can’t even imagine what that would be like. I graduated college in 1983 and moved to Manhattan. I’m a native New Yorker, so it wasn’t that big a jump, you know? And the first 13 years of my career. There was some success there and some highlights, but for the most part it was a lot of despair as I was trying to figure out who I was and what I wanted to be. I graduated with a degree in English Literature, so I wasn’t really prepared for the big time, and at the time, I wasn’t in a place where I either could or wanted to go on for a higher degree. I wanted to live in Manhattan and, you know, be a working girl, so to speak. And because I didn’t have a lot of training or a lot of guidance or any money, it was really, really hard for me. And I was also grappling with a lot of unresolved trauma and was living on my own for the first time in my life.

Debbie Millman 00:51:59  And I often say that I consider that first decade of my career just experiments and rejection and failure and bit of humiliation and then quite serendipitously, ended up in the world of branding. You know, I had some skills in design coming out of college because I worked on the student newspaper, and the editor of the section also had to put the paper together, and that meant designing it. And that’s when I discovered my love of graphic design and began to develop the skills that were required to be a graphic designer. It was still pretty rudimentary, although I had, I think, a good eye and some good ideas. I didn’t at that time have the drafting skills that were required in the 80s. I developed them and and that was a good thing. Again, it was very serendipitous, a fluke that I ended up in branding. And then, as you were talking about earlier, discovered I had a natural ability for it. My brain just understood the psychological underpinnings of wanting to engage with products that made people feel either better about who they were, gave them more social confidence, made them feel like they were part of a bigger tribe, were enjoying a moment that they were engaging with that brand and what that did to our psychological makeup.

Debbie Millman 00:53:23  And though even that entry point was marked with difficulties, I came into an agency that was mostly comprised of young British guys, and I came in as a sort of loudmouth female American that was challenging for the first couple of years. Then I was embraced, mostly because I was doing well, you know, for the company. I was bringing in a lot of business. And so I was then finally embraced. But then, you know, when I was bringing in the business, part of my original offer to join the company was that I would begin to earn equity. I knew that the senior partner was interested one day in selling the company. And so I wanted to be part of that. And initially there was some resistance as. There would be for anybody asking for equity. And I had to to say that if I didn’t get equity and I don’t know where this courage came from, then I’d have to leave the company. And I didn’t want to leave the company because it was the first time in my life that I was really successful and happy doing what I was doing.

Debbie Millman 00:54:25  And at this point, I’m in my mid to late 30s. I didn’t become a partner at Sterling until I was 38, and I was terrified that they’d call my bluff and say, okay, well, sorry, you know, we don’t want to give you shares. and then I did get on an equity path, which became, you know, really important to my life. But I remember that night going home and thinking, oh, my God, what have I done? You know, I made this threat that I would leave this job that I love, that I’m finally good at something, you know, from a professional point of view. And and then thankfully, that worked out. But there were a couple of moments in there where I wasn’t sure it would, and working in new business the way I did is a constant street fight because you’re competing with other agencies. You’re at the whim of what a client might or might not want. I was the chief rainmaker for a long time in the division at Sterling that I was running.

Debbie Millman 00:55:23  You can only imagine what that pressure was like, especially for somebody that is not only competitive, but using their success to boost their self-worth. And that is really challenging because if you aren’t successful at something, if you don’t win a piece of business, that can just decimate whatever little self-esteem you’ve built. And so I had to get off that hamster wheel. But that’s a really long time. And I still grapple with that. Not necessarily in Rainmaker, but just in any area where I have to prove myself.

Eric Zimmer 00:55:55  Yeah, I think that that is something that many of us wrestle with and I think we can get better at, but I don’t know if it ever completely goes away.

Debbie Millman 00:56:03  Yeah. I’ll let you know. I’m still searching for that. That’s my holy grail, Eric. That’s my holy grail. Just to feel good as is.

Eric Zimmer 00:56:12  Well, that is sort of the ultimate way to be. Because, as we’ve said, you sort of can’t necessarily make what is aligned with the way you want it to be.

Eric Zimmer 00:56:24  So a certain ability to be like, okay, this is I’m going to be okay with with what is is the thing many of us are striving for. I suspect that there’s a creature, though, who may be good at this is Maximus Toretto. Blueberry adept in this skill?

Debbie Millman 00:56:44  Well, Maximus Toretto. Blueberry. The little multi-GPU we adopted during Covid is really an example of what it means to live in the moment, to have utterly no self-consciousness consciousness about any of our bodily requirements and is is proof that unconditional love exists. So Max is not my first dog. Max is Roxanne’s first dog, and so it’s wonderful to see all of those realizations birth themselves in her and the realizations and the relationships she has with Max, which is just heart bursting. I can’t even explain it. But the first dog that did that for me was my dog, Duff. And that was 25 years ago. One of the great loves of my life taught me what it meant to feel loved unconditionally and to love unconditionally. And that is one of the great, great gifts to the world that our pets can do for us.

Debbie Millman 00:57:47  And so I love to have my furry, my furry family around me. We have two cats and a dog.

Eric Zimmer 00:57:55  Before we wrap up, I want you to think about this. Have you ever ended the day feeling like your choices didn’t quite match the person you wanted to be? Maybe it was autopilot mode or self-doubt that made it harder to stick to your goals. And that’s exactly why I created the Six Saboteurs of Self Control. It’s a free guide to help you recognize the hidden patterns that hold you back and give you simple, effective strategies to break through them. If you’re ready to take back control and start making lasting changes. Download your copy now at one UFI eBook. Let’s make those shifts happen. Starting today, one you feed e-book. Well, I think that is a beautiful place for us to wrap up with the happy image of Maximus and your wife and your old dog. And I think it ties right back to kind of where we started, which is nature. Dogs are are part of nature, and there’s a special type of connection that comes from being in partnership with nature.

Debbie Millman 00:59:00  Yeah. And also witnessing what grows and what develops and what evolves with or without our participation.

Eric Zimmer 00:59:09  Well, Debbie, thank you so much. It’s always such a pleasure to talk with you. And I appreciate you joining us.

Debbie Millman 00:59:14  Eric. Thank you. Thank you so much for all of your kindness and generosity to me. And thank you for a really nice interview.

Eric Zimmer 00:59:21  Thank you so much for listening to the show. If you found this conversation helpful, inspiring, or thought provoking, I’d love for you to share it with a friend. Sharing from one person to another is the lifeblood of what we do. We don’t have a big budget, and I’m certainly not a celebrity. But we have something even better. And that’s you just hit the share button on your podcast app, or send a quick text with the episode length to someone who might enjoy it. Your support means the world, and together we can spread wisdom. One episode at a time. Thank you for being part of the one You Feed community.

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