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Was just at the gym today and
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We are coming up on the 10 year anniversary of the Daily Stoic book Daily Stoic website which also means we're coming up on the 10 year anniversary of the Daily Stoic Shopify store. We've been using Shopify since the very
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beginning with Daily Stoke.
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We sold a print I think first and then shortly thereafter we came out with the Memento Mori coin and we've used Shopify because we love it. We even expanded it out to the bookstore when we opened the bookstore, I guess this would have been in 2020, 2021. So been using Shopify forever because Shopify is the best and the biggest commerce platform there is. It's behind millions of businesses all around the world. 10% of all e commerce in the US is with Shopify. It helps you tackle inventory, payments, analytics and more. You don't have to have multiple websites. You don't have to figure out who hosts or you know all this stuff. Shopify is everything all in one place making your life easier and your business operate smoother. They've also got great customer service. Start your business today with the industry's best business partner, Shopify and start hearing with Shopify today. Sign up for your $1 a month trial at shopify.com stoic go to shopify.com
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stoic
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welcome to the Daily Stoic podcast designed to Help bring those four key stoic virtues, courage, discipline, justice, and wisdom
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into the real world.
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Hey, it's Ryan. Welcome to another episode of the Daily Stoke podcast. Okay, so I had a surreal experience a couple of weeks ago. I get this Instagram dm, a text over the weekend says, hey, I'm a producer for Harpo. That's Oprah's company. Would you have a minute? I want to ask you a question. I said, okay, this is a. 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 Obstacles Away, if I would fly out 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. I'm 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. And actually we just recorded it a few minutes ago with Jim Collins.
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Do you know who that is?
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And I said, of course I know who Jim Collins is. I love his books.
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Good to Great.
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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 is like he was in the green room, went to do 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 reached 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 23, 2026, said Ryan.
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I'm so looking forward to engaging with
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you in spirited conversation about what 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
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years of research, and two years of writing.
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I will be super curious how reading it might also change how you look at life. Enjoy Jim. And 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. 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 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 in 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's me talking with the great Jim Collins. 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 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.
D
Oh, yes. Yeah. What would you like to know?
A
Well, take us back to that afternoon you spent together on the Stanford campus.
D
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 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 book. And what I loved about the book was it was alternating chapters of her experience and his experience going through those difficult years, because they're both on a journey. 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 kind of Palo Alto foothills and the fog coming in over them on a wonderful day. And I was reading this book and as 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 as the hardest thing is that I'm reading it knowing that in a few days he and I are 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 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. 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 your Release date is December 31, 1972 or something. You have no idea how long this will last, what form it will take. 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 kind of a funny moment that happened early. He asked me, so what do you teach over at the business school? And I started to describe my approach to building a 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, me for a moment and he goes, you're not teaching business, you're teaching philosophy. And it was a classic Jim Stockdale moment.
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Yes.
D
So anyways, we're walking and I said, admiral Stockdale, I have to ask you, how did you not capitulate to despair? 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 there was a moment. I don't even know if I put this part in good to great. There's 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.
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Right.
D
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 across a big chunk of the Stanford campus. And I was just processing what he said, and he was just comfortable and in quiet, in silence. And then as we got close to the faculty club where we were going to have lunch, I said, admiral Stockdale, I'm curious who didn't make it out as strong as you? And he said, well, it's easy. It was the optimists. And I was like, well, I'm confused, given what you'd 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 Christmas, and Christmas would come and it would go, and 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 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 there are reasons why it's in good to great, even though it's 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 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 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 somebody is confronting, say, a disease situation that's touched my life, my wife's life, where you're 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 we got a lot to go through, and 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 course of a relatively short period of time, the way you come at life is, like, permanently altered. And that was my Admiral Stockdale day.
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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 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 might take that to me, 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 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. 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 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 it's not gonna happen for him, and it's not until the Navy sends him to Stanford, where He's getting 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 in your book you talk about the mentor professor that you had at Stanford and how these teachers can change your life. But on their last meeting, Rhinelander, famous, introduces him to Epictetus, the Stoic philosopher. And it's Epictetus who he thinks about in the Hanoi Hilton. And Epictetus's main teaching is this idea that we don't control what happens. We control how we respond to what happens. 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 wrote this, 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.
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But this.
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This destiny tapping him on the shoulder moment, but for many years, decades even, he doesn't know that. And he's struggling and resenting and fighting and frustrating, and yet all the while, he is being prepared for the moment that you ended up profiling. In the book where he is tested and he is asked whether he's got the stuff or not, and he manages
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to answer, well, yeah, and he comes out with that wonderful thing of his. I know how I would do. Right?
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Yes.
D
And he liked what he saw. I mean, is that he had no question for the rest of his life, because he did it.
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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, we think of these sort of material or these objective performance metrics, but I think as you go, and some of the most fascinating people in the book, particularly. Particularly that football player who goes on to become a judge, you realize that actually there's a whole other set of metrics that you're not even thinking about measuring yourself, that in the end, those are the important ones.
D
Yeah, I think 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 look at as icons and and luminaries. John Glenn or Toni Morrison or Robert Plant and Jimmy Page or Gerald R. Ford and Jimmy Carter. These people that Benjamin Franklin and Roger Sherman and Barbara McClintock and Grace Hopper and 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 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 and the early 1910s. And there's these. You can see how she's talking about it when she actually disembarks. But you can only do that with people whose lives allow you to do that. So to me, this is about. It's about life. It's not about their success. It's not about their fame. 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 known for. And so just as we get into this, I really want to set 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 life choices and what we learn from the patterns of those that really were 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 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 would be in a higher quadrant 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 that someone like Admiral Stockdale had, that it just kind of puts all that other stuff off into a bucket of not irrelevance. But it just, like this is so pristine.
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Yes.
D
And I use the word intimidating because it's such a rarefied standard and yet it's not. Not easily seen.
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Yeah. And it's hard to measure, as you're saying. I thought that was one of the interesting things in the beginning of the book where you're talking about how on good to Great or how the mighty fall, you're able to measure pretty objectively whether it's shareholder value or the destruction of shareholder value or longevity or earnings. How you're measuring a life is difficult. And some of these deeper values, the things that, that we immediately recognize as being worth more than these other things, are harder to track. And I think that is what's so fascinating about Stockdale is that towards the end, he ends up achieving both a measure of fame and then, unfortunately, I think, to our shame, a level of infamy because of how that. Not how he handled 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. I guess it's always worth stipulating that that many of the greatest individuals, the people who have lived truly impressive lives, we've just never heard 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. We just got home from a spring
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break trip, 12 hours of driving, we're pulling into the driveway, and we're like, oh, man, what are we going to have for dinner tonight? What are we going to have dinner for tomorrow? Because we don't have time to go to the grocery store. But then we remembered we had a
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Bugs it's spring here in Texas and
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D
Up. 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 a life after that. And I look at, you know, whether it be famous people like Robert Plant 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, 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 a choice early, which is that in the opening chapter, my first pair of people, I thought 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, including they were amazingly good illustrations of what the first key chapter after the intro chapter lays out. But also, not a lot of people know Barbara McClintock. And so when you meet her. So if you met, say, Jimmy Carter and Gerald Ford in chapter one or somebody kind of much more sort of visible roles, you'd have a preconception as to who and what they are. 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, she's one of the figures that is the most seminal in all of history. But you could then engage with them as human beings, not their Persona as human beings. And you'll notice that a number of the more well known people I sort of stacked towards the end of the book because I wanted people to meet them as people rather than Personas.
A
Yeah, people wrestling with the same stuff that people have always had to wrestle with, which is, what do you do next? What actually matters? How do you bounce back from adversity? How do you get to the fog?
C
Totally.
A
I mean, one of the other characters I loved in the book and happened to be a classmate of Stockdale's at the Naval Academy was Jimmy Carter. And the idea that his cliff was not being pressed president is such a fascinating thing. And he actually was a great president and did a lot of great things and held the office well. But the idea that actually his greatness came after he was no longer President strikes me as a pretty sort of powerful call to all of us that you think your best years are behind you or you think your best shot is behind you. But actually, that's a choice you get to make.
D
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 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.
A
Big thumbs down.
D
Yeah, big thumbs down at the end of your first term. Sorry, here's your pink slip. You've been fired by the American people. And of course, Carter had. They had been political adversaries, because in the 76 election, it was Ford versus Carter. And Carter, he was stunned and shocked that he was not going to have a second term. I think he was 56, if I recall the year correctly. 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, it's just fascinating. Kind of the first thing that happened when they returned to Plains is he's like, let's go up. And they began, like, remodeling the upstairs attic of the house. It was just, I gotta lose myself in doing this.
A
And 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.
D
Absolutely. He had put his assets into a blind trust, and some other people had kind of taken care of the family business. And when. And he got. 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 that marvelous moment of kind of coming up with the idea that. But while as president, many ways, the best ways he was most really encoded to really, really operate was in brokering these things, like bringing together people for Middle east negotiations and so forth, Camp David Accords. And what he did was he said, I want to continue doing that, but there isn't a place for that. And is 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's right, he lived to be a hundred.
A
Yes.
D
And think about everything 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. One of my favorite, though, things in the book is, I think, 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 things I loved is how these two adversaries became friends, really close friends, and they worked together on initiatives and issues, and they did joint things at the Carter center and so forth. And they really grew to love each other as friends. And both of them had this incredible sense of dedication 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, 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. Act, which is in many ways a very big act.
A
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 U.S. 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 sort of intense hazing at the Naval Academy or plebe year. And so as. As this, this young man is going through the hazing process that is designed to drive him out. You know, Carter hears it from his room, and the two of them had had been running on the cross country team together. And Carter from the Deep south sort of walks out of his room and, and walks up to, to Wes Brown and throws his arm over his shoulder and says, you know, hang in there, don't. Don't let him get to you. And, and this act of sort of crossing this racial barrier and the decision to sort someone else who, you know, he could have easily turned his, his eyes away or closed his heart off to was this sort of moment of, of, of grace and decency that again, when you, 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 reach across the aisle and ask you to deliver their eulogy or, you know, that someone who's being discriminated against, or do you want them to sort of be bragging about your net worth at the end?
D
Actually, that brings me to a question that I'd like to ask you, if you don't mind, through your lens of having really made yourself a student in the great stoics and the way that they thought and how their timeless ways of thinking and living living are very relevant in any era and certainly our own. And congratulations on that. I think it's a marvelous vein to make a real contribution. So one of the things that happened for me in writing the book is the ways in which I ended up sort of changing my views on things a lot. I have a whole table in chapter 13. You, you may have, you know, whereas like on one side, as I used to believe, and then after 12 years of research, now I believe and I could see my lens on the world changing. That'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 then as I studied the lives in this work and most of them have passed away. So I've been able to look at them all the way up to the 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 will be a legacy in, 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 and founding of the nation, or Alice Paul and Lucy Burns with the legacy of what happened with women's suffrage. It's not that there weren't legacies, but their focus on it seemed to be pretty 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.
A
Yeah.
D
And so job one was to keep choosing things that would express those. And many of them kept choosing things they felt responsible for today right in front of them and executing on that. And then one day the clock ran out 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 Joanne was like, well, yeah, that's a self centric question, number one. And number two, you won't be here to enjoy it anyways. And number three, why would you spend any time on that when you have so much left to do? And then as I studied the people and the research, that's exactly how they went about things. They really. And I shifted and so I no longer think, I think that this concern about legacy is like a danger almost because it takes you off of what's right in front of you that you have left 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, because I used to think it was important. Now I don't think it's very important at all. What do you think?
A
It's something the Stoics talk a lot about. One of the fundamental ironies of Marcus Aurelius's Meditations is you're reading a book that is still a bestseller 2,000 years after it was written by one of the most famous people 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, he says 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. And then one of my favorite passages is he lists. 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 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 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? Or, you know, like, you're. I forget what, which book, which companies are in the book, 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 experiences as you can? No, 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. And you detach from results and you detach from recognition and you retach 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 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.
D
You know, it's interesting. I was really struck by how most of the people in the study, and I think there are some things that they did that were just brutally difficult that they did. It's hard to say, well, 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. It wasn't 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 as I love singing.
A
Yes.
D
I just want to sing. Right.
A
Bruce Springsteen has talked about how it's called playing for a reason. And he loves to play music. You know that. That's the joy of it.
D
Yeah. And you never know. That's the other thing. One of the things that was fascinating to me as I just kind of looked at the different lives is often how what they were doing, they had no idea what impact it would have.
B
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D
I think about my two writers, Toni Morrison and Barbara Tuckman. And Barbara Tuckman was off study, you know, she was just fascinated with whatever subject of history she picked up and decided to learn about, right? And then she ends up writing this book, the Guns of August. And one of my favorite little stories in there is about how there are series of sort of chant President Kennedy reads the Guns of August, which is about the start of World War I, 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 I. He happens to be reading Tuckman's Guns of August before the Cuban Missile Crisis, and then ends up applying the lessons of, of those opening days of World War I through her book to say, I don't want ever this thing to be 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 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 whole kind of arc of the history of what happened in those opening days of world one. I'm 100% certain she wasn't thinking and then the President will read it and we'll 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. 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. From them, but it wasn't. They didn't even know that those outcomes would come from them.
A
Right.
D
And the focus was right here, what they were doing. And the outcomes were often enormously unpredictable.
A
Yeah. You don't influence a president and change the course of world events by sitting down to write a book to influence the president. You influence the president because you love history so much that you put something down that is of value. Another great example of this is the book the Great Influenza by John M. Barry. He becomes fascinated with 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, you have to love the thing so much, and I think maybe it's Toni Morrison. You quote in the book, the only reason to write something is because you can't not write it. And so 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 also, at the very least, even if nobody had read Guns of August, Barbara Tuchman succeeded because she enjoyed writing the Guns of August.
D
August, right. 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.
A
Yes. Which means the fact that it was published was extra on she did it because she enjoyed it. And then all the success was extra, which I think ties back to stoicism. This is the idea of, hey, the part you control, you did well. And then you got lucky. Right. You got lucky 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. Yeah.
D
So first of all, kind of zooming way out, kind of to put that in perspective as you know, one of the kind of ways I came to understand the way life works at its best is this idea that there are times when people are kind of in frame and out of frame. And what, for those who might be listening, what that means is the idea that we all have kind of a set of encodings. Ryan, you have different encodings than I have, and they're like a constellation. It's just these capacities we have Within. And then they're awaiting discovery through the experiences of life. So we were talking earlier about Admiral 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.
A
He'd been training for it without knowing it his entire life.
D
Exactly. And then, boom, he's in frame. And he was the perfect leader for that setting. And what I saw is that as the frame of life would shift at different points in your life, 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. 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. Business that didn't really. And then he, through a series of kind of almost accidental steps, ended up being able to get his pilot's license 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 at Royal Crown Cola, where he's an executive. Executives. Almost 10% of his life, but it's 0.2% of his memoir. And so it kind of shows that it's just kind of like a time that it was. Sure, it was fine, but it wasn't like what he was when he was.
A
It's the dog that didn't bark. It's revealing.
D
It really is. Exactly. And then back in frame as a senator and so forth. And being in frame means three things. One, 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, rather than that the purpose of doing what you're encoded for is to make money. Right. The arrow flips. And the third is that it's something that really ignites and feeds the fire with 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 confidence 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 active, out of frame, you're good enough at it, right? You're not necessarily. It's like being at Royal Crown Cola for John Glenn, right? Or taking chemistry classes like John Glenn. He would have become a doctor, you know. And through hard work and discipline and 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 get better at it. You get more opportunities, 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 spend more time becoming better paid at doing something at which you are not really in frame. 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 of 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 were caring for your family, you're supporting your parents, you're, you know, whatever the 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 of is written.
C
Right?
D
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 are in frame and everything clicks. And in the same life you can have multiple cycles of that fate, 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 just isn't, you know, it's okay or it's terrible or it's whatever. It's not the end of the story. It's never the end of the story until it's really the end. Foreign.
F
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Episode: If You’re Lost, You’re Asking the Wrong Question | Jim Collins (PT.1)
Date: April 9, 2026
Host: Ryan Holiday
Guest: Jim Collins
In this engaging conversation, Ryan Holiday sits down with legendary business author Jim Collins to discuss the themes of Collins’ new book, What to Make of a Life: Cliff, Fog, Fire, and the Self-Knowledge Imperative. Their dialogue weaves together Stoic philosophy, history, and business insights as they explore meaningful lives, enduring challenges, the illusion of legacy, and how pivotal life events—what Collins calls “cliffs”—reshape people’s journeys. A special emphasis is placed on figures like Admiral James Stockdale and Jimmy Carter, using their stories to illuminate the deeper metrics of a well-lived life, far beyond external success.
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Timestamps: 41:54–54:14
The conversation is thoughtful, warm, and reflective, rich in anecdotes and history, using a scholarly yet highly accessible tone. Both Collins and Holiday blend personal stories, historical analysis, and philosophical musings with humility and depth.
This episode offers a rich meditation on how to live a meaningful life: by embracing challenges without a guarantee of outcome, focusing on values and process over external measures of success, and continually seeking alignment between our unique abilities and life’s opportunities—even if it means starting over after a personal “cliff.” Both Stoicism and Collins’ research remind listeners that legacy is largely an illusion; what matters is the cultivation of character, resiliency, and the intrinsic rewards of the work that calls you.
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