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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