Make the Most of Your Life | Jim Collins

What if the reason you feel lost has nothing to do with direction and everything to do with the question you’re asking? Ryan sits down with bestselling author Jim Collins to explore the mindset that defines strong people, why success can mislead you, and what actually makes a life meaningful. Jim Collins is a bestselling author and one of the leading voices on leadership and human performance, known for books like Good to Great, which has sold millions of copies worldwide. His research-driven work explores what separates the truly exceptional from the average, with a focus on how people confront the biggest questions of leadership, purpose, and life. Jim Collins’ new book 👉 What to Make of a Life: Cliffs, Fog, Fire and the Self-Knowledge Imperative is out now! Grab a copy here📚 Pick up a copy of Good to Great by Jim Collins at The Painted Porch | https://www.thepaintedporch.com/🎥 VIDEO EPISODES | Watch the video episodes on The Daily Stoic YouTube channel: https://www.youtube.com/@DailyStoic/videos✉️ FREE STOIC WISDOM | Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail 📢 Share | ⚙️ Manage Subscription

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Ryan Holiday?

  Welcome to the Daily Stoic Podcast, designed to help bring those four key Stoic virtues, courage, discipline, justice, and wisdom into the real world.

• 0:15Ryan Holiday?

  Hey, it's Ryan. Welcome to another episode of the Daily Stoic Podcast. Okay, so I had a surreal experience a couple of weeks ago. I get this Instagram DM, a text over the weekend. It says, hey, I'm a producer for Harpo. That's Oprah's company. But would you have a minute? I want to ask you a question. I said, okay, this is a thing I'll do on the weekend. So I did. I reached out and it was a producer for Oprah Winfrey's show and podcast. And they wanted to know, she had just read my book, The Obstacle is Away, if I would fly out to Maui to talk about it for this episode she was doing. And I said, of course. I dragged the family along because any excuse to go to Hawaii is one I'm going to take. You take this long road up to her house there in Maui. Very nervous, talking to the producer beforehand. And I said, you know, are you guys recording a bunch of these? She said, yes, we batch these episodes.

• 1:00Ryan Holiday?

  And actually, we just recorded it a few minutes ago with Jim Collins. Do you know who that is? And I said, of course, I know who Jim Collins is. I love his books, Good to Great, of course, How the Mighty Fall. And I actually, I said, I have a copy of the galley of his new book on my desk, which I didn't bring on this trip because I didn't have room in my suitcase. But I need to read it because I'm about to interview him. So we had just missed each other. The way they staggered the guests is they never had us overlap. It's like he was in the green room, went to the episode. And then as soon as he went to the episode, I went to the green room. We never got to see each other. But when I got home, I leached behind my desk there in the office and pulled down the manuscript. And it turned out there was a lovely note in it. This is from January 23rd, 2026. It said, Ryan, I'm so looking forward to engaging with you

• 1:43Ryan Holiday?

  in spirited conversation about what you read in these pages. His new book is called What to Make of a Life, Cliff, Fog, Fire, and the Self-Knowledge Imperative. He says, a spirited conversation about what you read in these pages. This is the best work of my life to date, and it transformed me in the process of 12 years, 10 years of research and two years of writing. I will be super curious how reading it might also change how you look at life in joy. Jim. It did. It did change how I look at life. It is a lovely book. I've always been a huge fan of his and was very excited to get to sit down to talk with him. So I am bringing you part one of my conversation now with the great Jim Collins, one of the bestselling

• 2:25Ryan Holiday?

  business writers of all time. He's worked with every CEO and company you can imagine. And most importantly, and this is where we start the episode, he is famous for coining something known as the Stockdale Paradox about the Stoic philosopher slash fighter pilot, Admiral James Stockdale on page 83 in Good to Great. In a way, a little bit of a tangent, interruption. It doesn't seem like it would be in this book about why some companies make the leap and others don't. But it's become this really famous thing and it introduced Stockdale to a huge audience and it's a fascinating look at sort of Stoic philosophy and the Hanoi Hilton. So that's where we kick off this conversation and then we get into a bunch of other stuff after that. But I'll just get into it here as me talking with the great Jim Collins.

• 3:11Ryan Holiday?

  I was fascinated with this book and particularly the list of people at the beginning because a bunch of these people are heroes of mine, people I've read about, people I've studied, people I've tried to base my life on. But there was one, one missing that I wanted to ask you about first. I know he's not a character in this book, but he is a character in this book. I wanted to ask you first and foremost, because it's where our work overlaps, about your time with Admiral Stockdale.

• 3:41Speaker 01

  Oh, yes. Yeah. What would you like to know?

• 3:45Ryan Holiday?

  Well, take us back to that afternoon you spent together on the Stanford campus.

• 3:50Speaker 01

  Yeah. So it was actually really an amazing experience for me and one of those moments in life that you can just kind of see your whole lens on life shift in a matter of minutes. And what happened was kind of the real sort of background of the story is that I was teaching my course on entrepreneurship and small business across the street from the Hoover Institute. I was over at the Stanford Business School and one of my- Students wrote his paper for my class on Admiral Stockdale and had gotten to know him through that. And then that led to the opportunity to have a wonderful meeting

• 4:32Speaker 01

  and conversation and lunch and a walk with Admiral Stockdale. And a couple of interesting things, even before I had that afternoon, I first of all, sat down and read. And I read his book, which he wrote in alternating chapters with his wife, called In Love and War. And for those who don't fully know the story of Admiral Stockdale, he was shot down in, I believe, 1967. He was the highest ranking naval officer in the Hanoi Hilton prisoner of war camp. He spent about seven years in the camp. And then one of the things that came out of it was this, this book. And what I loved about the book was it was

• 5:11Speaker 01

  alternating chapters of, of her experience and his experience going through those difficult years.

• 5:19Ryan Holiday?

  Because they're both on a journey.

• 5:20Speaker 01

  Both on a journey, right? And not knowing the end of the story. And I think what really, I remember very vividly sitting there in, I had this wonderful little office. It was kind of up on the third floor of the business school. And I could actually see the, the kind of Palo Alto foothills and the fog coming in over them on a, on a wonderful day. And I was reading this book and as I, I was in this marvelous setting and I found myself starting to get depressed as I read it. And I was trying to figure out like, why am I feeling depressed? Why is this feeling overwhelming to me? And I realized that what really struck me is the hardest thing is that I'm reading it knowing that in a few days, he and I are

• 6:02Speaker 01

  going to meet. We're going to be on the beautiful Stanford campus. We're going to have lunch together. I know he gets out of the prison camp. I know the sort of the end of that portion of the story of his life. And as I was reading about him in the camp and enduring, you know, periodic torture and isolation and all the things that they went through, all of a sudden, it was this thought of When he was there, he didn't know. He didn't know if this would be the end of his life. Right? I mean, he didn't know for certain if he would get out. It's not like when you come into the Hanoi Hilton, they give you, well, your release date is December 31, 1972 or something. You have no idea, right? And how long this will last, what format it will take.

• 6:44Speaker 01

  And it was the unknown of it, the uncertainty of it, the not knowing the end of it that struck me as really hard. So I met up with Admiral Stockdale. And I remember, actually, there was a kind of a funny moment that happened early. He asked me, so what do you teach over to the business school? And I sort of described my approach to building the class and wanting to challenge my students to think much more about kind of the role of building a company in their life and things like this. And he looks at me for a moment and he goes, you're not teaching business, you're teaching philosophy. It was a classic Jim Stockdale moment. Yes. So anyways, we're walking and I said, Admiral Stockdale, I have to ask you, how did you not capitulate to despair?

• 7:27Speaker 01

  I know the end of the story, but you didn't know. And he said, well, I never capitulated to despair because I never wavered in my faith that I would not only get out eventually, but I would turn it into a defining event of my life that in retrospect I would not trade. And that there was a moment, I don't even know if I put this part in Good to Great. There's this also this point where he said, you realize, Jim, I'm kind of the lucky one in this, between the two of us. Because I know how I would do, and you probably never will. Right.

• 8:10Speaker 01

  And so I took that in and we walked for a long, long time. There was a long silence. One of the things that really struck me about Admiral Stockdale that day was his incredible comfort with really long silence. We walked for probably, you know, across a big chunk of the Stanford campus. And I was just processing what he said and he was just comfortable and quiet. In silence. And then as we got close to the faculty club where we were going to have lunch, I said, I'm curious, who didn't make it out as strong as you? And he said, well, it's easy. It was the optimist. And I was like, I'm confused, given what you said before. And he said, well, let me help you understand what I mean by that. It's those who said, we're going to be out by

• 8:54Speaker 01

  Christmas. And, and Christmas would come and it would go. And then we're going to be out by Easter. We're going to be out by Thanksgiving. We're going to be out by Christmas again. And it would come and go. And they died of a broken heart. And, and this was when this kind of fusing of these two views came together that later, I ended up calling the Stockdale paradox in good to great. And the reasons why it's in good to great, even though it's, you know, studying companies, because a lot of the leaders I studied embodied some version of what I call the Stockdale paradox, which is this ability on the one hand, to have kind of an unwavering

• 9:29Speaker 01

  faith in the end result. But at the same time, having this really disciplined ability to confront the brutal facts of your current reality of your existence as they actually are. We're not out of here by Christmas. We don't know how long this will be. And, and that just came together for me as a frame. And interestingly, I have found the Stockdale paradox incredibly powerful in multiple times, particularly, for example, if, if somebody is confronting, say, a disease situation, you know, that's touched my life, my wife's life, you know, where you're, you're

• 10:12Speaker 01

  wrestling with the uncertainties of what disease might mean. And kind of again, embracing the Stockdale paradox of some sense of unwavering faith, we can get to the other side. But the brutal facts are, you know, we've got a lot to go through. And this may, it might be a long time before I'm out of this. I'm not going to be out by April, or December, or whatever. And other aspects of life, when you're going through something that's just Out of your control, that Stockdale paradox has for me been an enormously powerful frame. So it's like you have one of those great teachers you meet for a moment. And in the, and in the course of a relatively short period of time,

• 10:53Speaker 01

  the way you come at life is like permanently altered. And that was my Admiral Stockdale day.

• 10:59Ryan Holiday?

  Well, I have goosebumps and I want to tell you a little bit of a story. I'll tell you why I thought of him so much as I was reading your book. So, so Stockdale goes to the Naval Academy in 1943. And as his father drops him off there, his father says, I want you to be the best man in the hall. Like, I want you to be the best graduate out of the Naval Academy there is. So you, you might take that to mean number one in your class, the first to make Admiral, the first to do X, Y, and Z. And it's really interesting because he struggles for the, the next 20 years. And I don't mean struggle in terms of failure, but he's not number one in his class. He doesn't make the football team.

• 11:40Ryan Holiday?

  You know, one of his classmates wins the Medal of Honor in Korea and he doesn't get a chance to serve in Korea. He misses out on all these plum assignments. One of the characters in your book is John Glenn. You know, John Glenn and him and Stockdale are both at test fighter pilot school together. And John Glenn becomes the famous one and Stockdale doesn't. I, I was just reading a newspaper article. When Stockdale is promoted to commander in his hometown newspaper and it says, Stockdale is famously a classmate of John Glenn. So he's in the shadow of all these other famous people. He keeps missing his moment, right? And he thinks that, that it's, it's not going to happen for him.

• 12:24Ryan Holiday?

  And it's not until the, the Navy sends him to Stanford where he gets, he's getting his, his, his degree in international relations or economics or something like this, that he bumps into a teacher like you're talking about, one of those teachers that changes your life. And a professor there named Philip Rhinelander takes him under his wing. I know you, in your book, you talk about the, the mentor. Professor that you had at Stanford and how these these teachers can change our life. But on their last meeting, Rhine Lander famously introduces him to Epictetus, the Stoic philosopher. And it's it's Epictetus who he thinks about in in the Hanoi Hilton. And and Epictetus's main teaching is this idea that, you know, we don't control what happens, we control how we respond to what happens.

• 13:09Ryan Holiday?

  Like, we don't control whether we get out, but we control who we are while we're in the prison. And ultimately, we control whether we make a good showing of ourselves. And so I think, you know, you you wrote this lovely book about, you know, how do you create a meaningful, purposeful life that matters? Not necessarily a life filled with plaudits and success, although that can be part of it, but but a good life. And and Stockdale strikes me as such a compelling example of someone who destiny actually does have this incredible opportunity in store for him, if you want to call it an opportunity. But this this destiny tapping him on the shoulder moment. But for for many years, decades even, he doesn't, he doesn't know that.

• 13:52Ryan Holiday?

  And and and he's struggling and resenting and fighting and frustrating. And yet, all the while, he is being prepared for the moment that you you ended up profiling in the book, where where he is tested and he does, he he is asked whether he's got the stuff or not. And and he manages to answer well.

• 14:13Speaker 01

  Yeah, and he comes out with that wonderful thing of his, I know how I would do.

• 14:17Ryan Holiday?

  Right?

• 14:17Speaker 01

  Yes. And he liked what he saw. I mean, he said, he had no question for the rest of his life because he did it.

• 14:26Ryan Holiday?

  What's best, like being the best man in the hall? When we're young, we so often think is the most money, the best job, the highest rank. You know, the we think of these sort of material or these objective performance metrics. But I think as you go, and some of the the most fascinating people in the book, particularly that that football player who goes on to become a judge, you realize, you realize that actually there's a whole other set of metrics that you're not even thinking about measuring yourself, that that in the end, those are the important ones.

• 14:58Speaker 01

  Yeah, I think, you know, so it's actually worth noting just here as we get into the conversation. The people that are in this book are largely folks who we would, you know, look at as icons and luminaries. John Glenn, or Toni Morrison, or Robert Plant and Jimmy Page, or Gerald R. Ford and Jimmy Carter. Or, you know, these people, Benjamin Franklin and Roger Sherman, and Barbara McClintock and Grace Hopper. And these, these, these people who in their worlds had such a huge impact. But I only have people of that stature in the book because that's where the data is. And I really wanted to study really how they wrestle with the question of constructing and reconstructing a life

• 15:42Speaker 01

  and answering the question multiple times of what to make of a life. But if you're going to study people, you have to have people where you have lots of information, including some contemporaneous information. I want to go back and I want to find articles on what Alice Paul was saying about what she was doing even before she was fully in the fight for suffrage. And so you can find these articles when she comes back from England in the, you know, early 1910s. And there's these, you can see how she's talking about it when she actually disembarks. And, but you can only do that with people whose lives allow you to do that. So I, to me, this is about, it's about life. It's not about their success, it's not about their fame.

• 16:26Speaker 01

  And one of the most interesting things to me is how a number of the people in our study went from very visible walks of life to at another time of life, they chose a much more private side of their lives as well. And that some of the most impressive parts of their lives were the things that they weren't necessarily the most, the most known for. And so just as we get into this, I really want to set the, the frame for our conversation for anybody who's listening, which is you and I are interested in the questions of how people wrestle with the questions of living and of life. And that's what I was looking at. It's not the questions of how they became successful and famous. And it is their

• 17:08Speaker 01

  Life choices and what we learn from the patterns of those that really were of of real interest to me. And then I go back to Stockdale, which is that not that many people knew about Stockdale. I think more did after writing about him in Good to Great. But I have had the great joy of and privilege of meeting a whole lot of amazing people over the course of my journey so far. There are very few that stand in my mind as when you talk about those that would be kind of in the category of the best, right? That that would be in a higher quadrant

• 17:48Speaker 01

  than Admiral Stockdale. And it has nothing to do with the success or fame or stature of anybody. It has to do with when you see the just intimidating level of character.

• 18:02Ryan Holiday?

  Yeah.

• 18:03Speaker 01

  That someone like Admiral Stockdale had, that it just it just kind of puts all that other stuff off into a bucket of not irrelevance, but it just like this is so pristine.

• 18:18Ryan Holiday?

  Yes.

• 18:19Speaker 01

  And I and I use the word intimidating because it's such a rarefied standard. And yet it's not easily seen.

• 18:26Ryan Holiday?

  Yeah, and it's it's hard to it's hard to measure, as you're saying. I thought that was one of the interesting things in in the beginning of the book where you're talking about how, you know, on on Good to Great or or how the mighty fall, you know, you're able to to measure pretty objectively, you know, whether it's shareholder value or the destruction of shareholder value or longevity or, you know, or earnings, how you're measuring a life is difficult, right? And and some of these sort of deeper values, the the things that that we immediately recognize as being worth more than these other things are harder to track. And and I think that is what's so fascinating about Stockdale is that towards the end, he he ends up achieving both a measure of fame and then and then unfortunately, I think to

• 19:10Ryan Holiday?

  our shame, a level of infamy because of how that that not how he handled the president, the vice presidential run and then how we as a society. reacted to it, but his was a quieter form of greatness that is always a struggle as a writer, because you know, you, you want to, as you said, you, you have to have the documentation. But also, as you're picking stories, who you're going to write about and who you're not going to write about, there's an extra level of resonance when the people have heard of those people, right? Like, the reader has a natural inclination to, to want to read about famous men and women. And so I guess it's always worth stipulating that, that many of the greatest individuals, the people who've lived truly impressive lives, we've just never heard

• 19:50Ryan Holiday?

  of. And just because when we're analyzing what that looks like, there's a certain publication bias to it. These are, these are just representatives who are in some ways not representative of most people.

• 20:14Speaker 01

  You know, actually, let me just pick up on that for a moment, because I, I thought about this when I was actually writing the book about the sequencing of which pairs of people would, would come at different points in the book. And, and it really ties to what you're describing. And, you know, as you know, the, the basic method was looking at pairs of lives of people on a similar trajectory, and then they share a similar cliff event, which is a place where your life is really hit with an event that forces choices, big choices often about what comes next. And maybe your life as you knew it before is over and you have to reconstruct the life after that. And I look at, you know, whether it be famous people like Robert Plant

• 20:55Speaker 01

  and Jimmy Page with the end of Led Zeppelin, or Alice Paul and Lucy Burns with having achieved suffrage and facing the question of, you know, what's the rest of their lives? But, you know, as I was, as I was picking, I could have picked any pair of people for any chapter. So each concept in the book, all the pairs, all the people in them reflected the concept of that. But I had to pick which pair I would highlight for any given chapter. And I made it, I made a choice early, which is that in the opening chapter, my first pair of people, I thought really Really hard, who should be the opening pair for people? And I picked Barbara McClintock and Grace Hopper. And the reason I did that, one of the reasons I did that, there were multiple reasons,

• 21:38Speaker 01

  including there were amazingly good illustrations of what the first chapter, first key chapter after the intro chapter lays out. But also, not a lot of people know Barbara McClintock.

• 21:51Ryan Holiday?

  Yeah.

• 21:51Speaker 01

  Right? And so when you meet her, so if you met, say, Jimmy Carter and Gerald Ford in chapter one, or, you know, somebody, you know, much, you know, kind of much more sort of visible roles, you'd have a preconception as to who and what they are.

• 22:06Ryan Holiday?

  Yeah.

• 22:06Speaker 01

  But because you've likely never really encountered Barbara McClintock, and not that many people, even Grace Hopper in computer science before, you can engage with them as people because you're meeting them as people for the first time. You're not meeting their persona because Barbara McClintock doesn't really have a larger-than-life persona for most of us. And Grace Hopper, unfortunately, hopefully she'll have more of one because I think in the world of computer science, he's one of the figures that is the most seminal in all of history. But you could then engage with them as human beings, right? Not their persona as human beings. And I, you'll notice that a number of the more well-known people, I sort of stacked towards the end of the book.

• 22:50Speaker 01

  Because I wanted people to meet them as people.

• 22:53Ryan Holiday?

  Yeah.

• 22:53Speaker 01

  Rather than personas.

• 22:55Ryan Holiday?

  Yeah, people wrestling with the same stuff that, that people have always had to wrestle with, which is, you know, what do you do next? What actually matters? How do you bounce back from adversity?

• 23:07Speaker 01

  How do you get through the fog?

• 23:09Ryan Holiday?

  Totally. I mean, one of, one of the other characters I loved in the book and happened to be a classmate of Stockdale's at the Naval Academy was, was Jimmy Carter. And the idea that, that his cliff was not being president is such a fascinating thing that, that,

• 23:24Speaker 01

  Yeah.

• 23:24Ryan Holiday?

  That, and, and he actually was a great, a great president and did a lot of great things and, and held the office well. But the idea that actually his greatness came...

• 23:36Ryan Holiday?

  After he was no longer president strikes me as a pretty sort of powerful call to all of us that you think you think your your best years are behind you, or you think your best shot is behind you. But actually, that's a that's a choice you get to make.

• 23:53Speaker 01

  I think it's a wonderful pair to bring up Gerald Ford and Jimmy Carter, Gerald R. Ford. And Carter, of course, is they were they were matched. The cliff I picked for them was they each got fired by the American people. I mean, it's one thing to get fired. It's another to get fired by millions of your fellow citizens.

• 24:14Ryan Holiday?

  Yeah, big thumbs down.

• 24:15Speaker 01

  Yeah, big thumbs down. At the end of your first term, you're, you know, sorry, you're, you're, here's your pink slip. You've been fired by the American people. And of course, Carter had, they had, they had been political adversaries, because in the 76 election, they were, it was Ford versus Carter. And, you know, Carter, he was stunned and shocked that he was not going to have a second term.

• 24:39Ryan Holiday?

  Yeah.

• 24:39Speaker 01

  I think he was 56, if I recall the the year correctly. He, he all of a sudden was in this flummox mode of, well, this is too early to retire, but I have no idea what to do. He didn't have a plan. He didn't really know what was going to come next. In fact, this is fascinating, kind of the first thing that happened when they returned to planes is he's like, uh, uh, let's go up and and they began like remodeling the upstairs attic of the house. You know, it was just like, I gotta lose myself in doing this. And

• 25:08Ryan Holiday?

  I think he was even in debt, right? Like, I think the business was in turmoil. Like, he actually left the presidency in worse shape than he entered it.

• 25:16Speaker 01

  Absolutely. He had put his assets into a blind trust, and some other people had kind of taken care of the the family business. And when he got, you know, and then he focused on being president, and then all of a sudden, they discover not only were they out of the White House, they had a massive debt that they had to work through. And so they had a financial cliff as well to work through coming out of it. And he wasn't at all sure what he wanted to do. And then he had this that marvelous moment of kind of coming up with the idea that, well, as president, so many ways, the best ways he was most really encoded to really, really operate was in brokering these things like bringing together

• 26:00Speaker 01

  people for Middle East negotiations and so forth, Camp David Accords. And, and he And what he did was he said, I want to continue doing that. And but there isn't a place for that. And it's the idea of the Carter Center becoming a place rather than just being a state library, a place that could keep that activity alive, which then. So if you think about it, he was 56. If my memory is right, he lived to be 100. Yes. And think about everything that that happened after that period of being 56. It could have just been the end, but it was actually in many ways, really just the beginning of what really added up to the long arc of Carter's role in the world.

• 26:44Speaker 01

  One of my favorite, though, things in the book is I think that the acts of, I don't know if I'd call them heroism, but just acts of wonderful standards is actually something that was a kind of a more personal and private act that he and Gerald Ford shared. And one of the things I most loved writing was at the end of the chapter where I write about the two of them, you probably remember this story. One of the things I loved is how these two adversaries became friends. Yeah. Really close friends. And they worked together on initiatives and issues and they did joint at things at the Carter Center and so forth. And they they really grew to love each other as friends.

• 27:29Speaker 01

  And both of them had this incredible sense of dedication to to the country, to service, to the responsibilities that they held dear. And late in life, Gerald R. Ford calls his friend Jimmy Carter and says, I think we should render one small additional service to our nation, essentially, that we should agree to do. And if whichever one of us passes first, the other one agrees to give the eulogy. And Ford passed first and Carter gave this eulogy. And what I love about that is that it was this kind of very personal act of demonstrating,

• 28:14Speaker 01

  of still accepting a responsibility, choosing a responsibility, not making a big deal out of it. It was just an act. And yet, when I came across it in the research, I was just so struck by the sheer beauty of what is actually a small act, which is in many ways, a very big act.

• 28:37Ryan Holiday?

  Yeah, I think it comes down to decency. My favorite Carter story happens at the Naval Academy. Both Stockdale and Carter overlap with this young midshipman named Wes Brown, who was basically the Jackie Robinson of the US Naval Academy, the first black graduate of the Naval Academy. And there'd been other black men who'd been accepted, but then they'd been driven out of the academy by the racism and this sort of campaign to keep them out of the Navy. And as you know, there was an intense hazing at the Naval Academy or plebeia. And so as this young man is going through the hazing process that is designed to drive him out, Carter hears it from his room. And the two of them had been running on the cross-country team together.

• 29:20Ryan Holiday?

  And Carter, from the deep south, sort of walks out of his room and walks up to Wes Brown and throws his arm over his shoulder and says, you know, hang in there. Don't let them get to you. And this act of sort of crossing this racial barrier and the decision to sort of root for someone else who, you know, he could have easily turned his eyes away or closed his heart off to was this sort of moment of grace and decency. That again, when you think about what you want to make of your life, do you want to look back and go, hey, you know, this person was a billionaire, this person started this, this person did this? Or do you want them to point to stories like that, that your political rival could

• 30:02Ryan Holiday?

  reach across the aisle and ask you to deliver their eulogy? Or, you know, that you supported someone who's being discriminated against? Or do you want them to, you know, sort of be bragging about your net worth at the end?

• 30:15Speaker 01

  And you know, actually, that brings me to a question that I'd like to ask you, if you don't mind, through your lens of having you really made yourself a student in the great Stoics, in the way that they thought, and how their timeless ways of thinking and living are very relevant in any era, and certainly our own. And congratulations on that. I think it's a marvelous, a marvelous vein to make a real contribution. So one of the things that I, that happened for me in writing the book, is there are ways in which I ended up sort of changing my views on things, a lot. I have a whole

• 30:59Speaker 01

  table in chapter 13, you may have, you know, where it's like, on one side is I used to believe, and then after 12 years of research, now I believe. And I could see my lens on the world changing. It's about 15 layers deep of these ways in which I ended up looking at things very different. And one of the ways that my thinking changed, my perspective changed, was on this question of legacy. Because, you know, people think a lot about, like, what's my legacy? How will I be remembered after I'm gone? And so forth. And what I was really struck by in, as I studied the lives in this work, over, and most of them have passed away, so I've been able, was able to look at them all the way up to the

• 31:38Speaker 01

  end, is how absent the concern about legacy was in the way they spoke and wrote and kind of went about their lives. And it's not that they didn't create a legacy. I mean, there's a legacy in Toni Morrison's books. There would be a legacy in the music of the great musicians that are in there. There's the legacy of whatever impact a president might have had, or of Franklin and Sherman and their legacy in founding of the nation, or right there, Alice Paul and Lucy Burns with the legacy of what happened with women's suffrage. So I thought there were legacies, but their focus on it was, seemed to be pretty

• 32:19Speaker 01

  absent. And what they were focused on was that they had their encodings, their gifts of what they could do in the world to be themselves. And one day, those would expire when they die.

• 32:32Ryan Holiday?

  Yeah.

• 32:33Speaker 01

  And, and so job one was to keep choosing things that would express those. If they, and, and many of them kept choosing things they felt responsible for today, right? Right in front of them and executing on that. And then one day the clock ran out, right? And they were done. And so I found myself, I used to, to think about this question a little bit. I remember people who started asking me, so Jim, what do you want your legacy to be? And I shared it with Joanne and, and Joanne was like, well, yeah, that's, that's a self centric question. Number one, and number two, you won't be here to enjoy it anyway. It's a number three, why would you spend any time on that when you have so much left to do? And, and then as I studied the people and the research, that's exactly how they went about things.

• 33:16Speaker 01

  They really, and I shifted. And so I no longer think, I think that this concern about legacy is like a danger almost. Cause it takes you off of what's right in front of you that you have left to, to do. And whatever happens after you're here is like kind of not really relevant in terms of how people think about you and so forth. And I'm curious through a Stoics lens, how you would think about it. Cause I used to think it was important. Now I don't think it's very important at all. What, what do you think?

• 33:46Ryan Holiday?

  It, it's something the Stoics talk a lot about. One of the fundamental ironies of, of Marcus Aurelius's meditations is you're reading a book that is still a bestseller. 2000 years after it was written by one of the most famous people and, and powerful and beloved and admired people of all time. And what he's talking about over and over again is how worthless legacy is. You know, he says, um, he says, uh, people who long for posthumous fame, forget that they won't be around to enjoy it. You know, he says, you know, this Alexander the Great and his mule driver, you know, the same thing happened to both of them in the end.

• 34:21Ryan Holiday?

  And, and then one of my favorite passages is he lists all these famous people from the recent and not recent past in his time. So, you know, he lists Vespasian, who was an emperor, like three or four emperors before him and a handful of others. You know, their, their main advisors and their powerful generals. And he goes like, how unfamiliar these names are already, right? And how quickly even the biggest, most powerful people are forgotten. And I think that's, you know, I came, I came to good to great a little late. It had probably already been out several years by the time I read it. And so I thought, I had an interesting experience going, wait, wait, is, is, is Circuit City in here? You know, like you, I forget what, which book, which companies are in the book.

• 35:06Ryan Holiday?

  But when you read a classic business book, you realize that even these classic companies don't stay classic that long, that there's this sort of parade of irrelevance that we're all a part of. And so when you meditate on that, does it make, does it make your life's work empty and meaningless? Does it mean you shouldn't try? Should it mean you just, you just have as much pleasure and fun and, and experience as you can? No, I, I think it goes actually to something you talk about in this book, which is that the best thing to do is focus on what you like doing and are good at doing and is meaningful to do for as long as you're able to do it.

• 35:50Ryan Holiday?

  And you detach from results and you detach from recognition and you detach from, you detach from that idea of legacy and you just, you get all the benefits you can from it now as a person who loves what they do and, and believes what they do is having a positive impact. To me, that, that's the legacy that you, you get to enjoy. And then any other legacy is, is, is for the people who come after you.

• 36:18Speaker 01

  You know, it's interesting. I was really struck by how most of the people in the study, and I, I think there are some things that they did that were just brutally difficult that they, that they did.

• 36:30Ryan Holiday?

  Sure.

• 36:30Speaker 01

  And it's hard to say, well, how did they, you know, how did they love some of the really hard things that they did? But for the most part, a lot of what was happening is the intrinsic satisfaction, the intrinsic joy of the actual doing, right? It wasn't the, the romantic idea of I want to be a writer. It was the love of the daily process of writing. Or the romantic, the idea of like, I want to be a surgeon. No, it's the enjoyment of actually preparing for and executing a care for the patient surgery with great surgical conscience, right? It's not so much the idea of I want to be a rock star is I love singing. Yes. I just want to sing, right? And

• 37:12Speaker 01

  And Bruce Springsteen has talked about how it's it's called playing for a reason. And he loves to play music, you know, that that's the joy of it. Yeah. And you never know, that's the other thing of one of the things that was fascinating to me. And in the, as I just kind of looked at the different, different lives is often how what they were doing, they had no idea what impact it would have.

• 37:45Speaker 01

  I think about my two writers, Toni Morrison and Barbara Tuchman. And Barbara Tuchman was off to study, you know, she was just fascinated with, with

• 37:55Speaker 01

  whatever subject of history she picked up and decided to learn about, right? And, and then she ends up writing this book, The Guns of August. And one of my favorite little stories in there is about how, you know, there were a series of sort of chances. President Kennedy reads The Guns of August, which is about the start of World War One and how basically a bunch of forces, when they finally got locked into place, even the most powerful people in the world couldn't untie the knot. And we had the great calamity of World War One. He happens to be reading Tuchman's Guns of August before the Cuban Missile Crisis. And then ends up applying the, the lessons of those opening days of World War One through her book

• 38:37Speaker 01

  to say, I don't want to ever this thing to be the, the missiles of October. We have to leave enough slack in the rope so that Khrushchev and I can find a way to a peaceful outcome here. And eventually they work through the Cuban Missile Crisis. And I find myself thinking, I find myself thinking of, of Barbara Tuchman sitting in her writing space, whatever that was, with her bits and pieces of paper, et cetera, and making sense of the things she saw when she drove around France and putting together the whole kind of arc of the history of what happened in those opening days of World War One. I'm 100% certain she wasn't thinking, and then the president will read it and will avert a nuclear war and we'll all be alive, right? I mean, that's not on her mind at all. She's just writing her book.

• 39:22Speaker 01

  And multiple times, I could see where people were just, they were in whatever they were doing. Sometimes there were these wild outcomes that came from them, but it wasn't, they didn't even know that those outcomes would come from them.

• 39:38Ryan Holiday?

  Right.

• 39:39Speaker 01

  And, and, cause, and the focus was right here, what they were doing. And the outcomes were often enormously unpredictable.

• 39:50Ryan Holiday?

  Yeah. You, you don't influence a president and change the, the, the course of world events by sitting down to write a book to influence the president. You, you influence the president because you love history so much that you put something down that, that, that is of value. Another great example of this is, is the book, The Great Influenza by John M. Berry. He becomes fascinated with the, the Spanish flu and he writes this book about it that George W. Bush reads and creates a pandemic preparedness division inside the White House because of this book. Like you, you have to love the thing so much.

• 40:31Ryan Holiday?

  And I think you, maybe it's, it's Tony Morrison you quote in the book, like the only reason to write something is because you can't not write it. And so you have to, you have to find what that thing is. And then that passion and that commitment and that fascination creates something that is infectious and compelling to others sometimes, not always, but, but also at the very least, even if nobody had read Guns of August, Barbara Tuchman succeeded because she enjoyed writing The Guns of August.

• 41:04Speaker 01

  Yeah, and it's interesting. There's a wonderful line, I think I put in there from Toni Morrison, where she says, "If all the publishers disappeared overnight, I'd still write my books."

• 41:14Ryan Holiday?

  Yes. Which means the fact that it was published was extra on like, like she did it because she enjoyed it and and then all the success was was extra, which I think ties back to Stoicism. Like, this is the idea of like, hey, the part you controlled, you did well. And then you got lucky, right? You got lucky in the in the sense that it lined up. This idea of loving what you do and doing it for that reason. You have the converse in the book, too. You talk about the curse of competence doom loop. Walk me through that.

• 41:49Speaker 01

  Yeah. So, so, so first of all, I'm kind of zooming way out, kind of to put that in in in perspective. As you know, one of the kind of ways I came to understand the way life works at its at its best is this idea that there are times when people are kind of in frame and out of frame. And what what for those who might be listening, what that means is the idea that, you know, we all have kind of a set of encodings, right? And you have different encodings than I have. And and they're like a constellation. It's just that these capacities we have within. And then they're awaiting discovery through the experiences of life. So we were talking earlier about Admiral

• 42:32Speaker 01

  Stockdale, who I, yeah, I think is, you know, when he ended up in the in the Hanoi Hilton, it was like the frame of his life. He was incredibly well encoded for that, for leadership in that situation.

• 42:43Ryan Holiday?

  He'd been training for it without knowing it his entire life.

• 42:46Speaker 01

  Exactly. And then boom, he's in frame. And he was the perfect leader for that setting. And and and what I, you know, saw is that as the frame of life would shift at different points in your life, The the the the frame of your life would only maybe capture a small set of your encodings. And then another shift in your life, a big, bright set of those encodings would come through the window. So we were talking earlier about John Glenn, and there are times of his life where he was kind of out of frame, right? He he was studying chemistry and thinking he might try to become a doctor. That wasn't working very well. Sports didn't work very well. His parents hoped he might come into the family business. That didn't really. And

• 43:27Speaker 01

  then he, through a series of kind of almost accidental steps, ended up being able to get his pilot sites and and learn to fly. And all of a sudden, these encodings came flooding through the window. He's in frame. That comes to an end. And then there's a time when he's out of frame, goes to work at Royal Crown Cola. One of my favorite little details is that it Royal Crown Cola, where he's an executive, is almost 10% of his life, but it's 0.2% of his memoir. And and so it kind of shows that it's just kind of like a time that it was it was sure it was fine, but it wasn't like what he was when he was.

• 44:05Ryan Holiday?

  It's it's the dog that didn't bark. It's revealing.

• 44:08Speaker 01

  It really is. Exactly. And then back in frame as a senator and so forth. And and being in frame means three things. One, a big set of your encodings are coming through the window. Not all of them, because you never find them all. Two, what matters to you is not the money you make from it, but you flip the arrow of money so that the purpose of money is to be able to do what you're encoded for.

• 44:32Ryan Holiday?

  Yes.

• 44:33Speaker 01

  Rather than that the purpose of doing what you're encoded for is to make money, right? The the arrow flips. And the third is that it's something that really ignites and feeds the fire within. It just boom, the fire just goes, just big, bright ignition of fire. And when you have all three of those, you're willing to flip the arrow of money, you're encoded for it, and it really feeds the inner fire. You were really in frame. Okay. So now let's go to the curse of competence doom loop. So the curse of competence doom loop is when you start down a path where through hard work and discipline and where you happen to be working or doing whatever, you're doing something at which you're kind of out of frame. You're, you're good enough at it, right?

• 45:16Speaker 01

  You're not necessarily, it's like being at Royal Crown Cola for, for John Glenn, right? Or taking chemistry classes like John Glenn, he would have become a doctor, you know, and, and through hard work and discipline and, you know, good personal habits and so forth, you can become competent and maybe even successful at it. And what happens then is because you're doing that, you, you get better at it, you get more opportunities to do more of what you don't really love to do and what you're not really encoded for because you're reasonably competent at it. And then you get better paid doing it. And what happens is that you're spend more time becoming better paid at doing something at which you are not really in frame.

• 46:00Speaker 01

  The years go by and then one day you wake up, you're 10, 20 years down the road and you realize that you're in an activity at which you're reasonably well compensated, but you're not really in frame. It doesn't really capture some of the best of your encodings. It doesn't really feed the fire. And the reality is you never really flip the arrow of money because the reason you're doing it is because it makes you the money. And then boom, you are in the curse of competence doom loop. And anybody can end up in it. I have great compassion for people who have this because there can be very noble reasons for why you ended up going down that path. You're caring for your family, you're supporting your parents, you're, you know, whatever the

• 46:40Speaker 01

  reasons might be, but it, the more time you spend there can be harder and harder to escape it to eventually end up really in frame, the way the people in our study did for phases of their life. And there were times that they were out of frame. I think that's one of the really big things about all this is that the die is never fully cast until the entire life is written. Right. And what, what's so powerful about looking across entire lives through these lenses is you can see times when When they're even lost and they're really out of frame and they're really confused and they're absolutely in the fog and then they can end up in a time when they really

• 47:22Speaker 01

  are in frame and everything clicks and in the same life you can have multiple cycles of that phase, of that phasing in and out. And that is actually something that when you go into a time when you feel like I'm out of frame, this is just isn't, you know, it's okay or it's terrible or it's whatever, it's not the end of the story. Yeah. It's never the end of the story until it's really the end.