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Wise Habits Reminders

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

May 30, 2025 Leave a Comment (Edit)

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.

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