Why Most Smart People Become Stupid - Ryan Holiday

Go see Chris live in America - https://chriswilliamson.live Ryan Holiday is a podcaster, marketer and an author. If intelligence were enough, the smartest among us would also be the wisest. Yet time and again, they stumble over life’s simplest lessons. Wisdom isn’t about knowing more; it’s about seeing deeper. So how do we shed the illusion of being ‘smart,’ and actually grow into wisdom? Expect to learn what Ryan learned from his near-death experience, what most people get wrong about wisdom, how daily habits compound into wisdom across a lifetime, what Ryan learned from studying the Wright Brothers, why in a culture of shortcuts and “life hacks,” how Ryan convinces people that wisdom is worth the long, uncomfortable path, what a Stoic would say about when you’ve lost yourself in life, why humility is such a crucial ingredient for wisdom, and much more… - 0:00 Why We Need to Push Outside Our Comfort Zone 5:13 Banning Books Isn't Ethical 16:42 Does Learning Keeps Us Humble? 27:48 The Value of Learning from Others 33:42 The Status Quo is There For a Reason 50:33 Start the Work Now - Your Wisdom Will Thank You 57:55 The Power of Remembering Who You Used to Be 01:03:45 How Stockdale Remained Unbroken 01:13:53 How Ryan Celebrates His Wins 01:20:03 Stoicism Regulates Your Life 01:25:13 Intelligence vs. Equanimity 01:29:16 What Makes Smart People Look Stupid? 01:41:46 How to Have Courage of Your Conviction 01:46:59 What are the Costs of Being Wise? 01:48:38 Where to Find Ryan - Get access to every episode 10 hours before YouTube by subscribing for free on Spotify - https://spoti.fi/2LSimPn or Apple Podcasts - https://apple.co/2MNqIgw Get my free Reading List of 100 life-changing books here - https://chriswillx.com/books/ Try my productivity energy drink Neutonic here - https://neutonic.com/modernwisdom - Get in touch in the comments below or head to... Instagram: https://www.instagram.com/chriswillx Twitter: https://www.twitter.com/chriswillx Email: https://chriswillx.com/contact/

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

• 0:00Chris Williamson?

  How did the live shows go? The last time we were talking.

• 0:02Ryan Holiday?

  Oh.

• 0:03Chris Williamson?

  We were discussing your upcoming live shows.

• 0:05Ryan Holiday?

  Yeah, I think it was, I was doing two in Australia and you gave me this advice. You were like, well, you told me that you'd done it with no notes. And usually like when you do talks at events, like they, they don't want you to just go up and give a speech. They want like a presentation, but these were, this was different. So yeah, I had to figure out how to do it with no, no notes, which was, um, it was interesting. Like it's good to pick arbitrary challenges and take something that you're good at. You've done a lot of times and just figure out a way to do it the hard way.

• 0:35Chris Williamson?

  Yeah, what's new?

• 0:36Ryan Holiday?

  Yeah. And so I had to sort of reinvent it from scratch. It was challenging, but good. It's actually funny in Mark Schuhr's meditations, he talks about practicing, holding the reins with your non-dominant hand. And so just like, what, what's the way that you're comfortable doing it? What's the way you normally do it? And then how do you force yourself to do it? Not the way that you like to do it. And to force yourself to do it in front of, the way you're not comfortable doing it in front of 2,000 people.

• 1:04Chris Williamson?

  Huge fucking audience.

• 1:05Ryan Holiday?

  Is it, is a, you know, it's a whole thing.

• 1:07Chris Williamson?

  Difficulty plus.

• 1:08Ryan Holiday?

  Yeah.

• 1:09Chris Williamson?

  I've always thought about doing a podcast episode with a guest that somebody had organized for me.

• 1:15Ryan Holiday?

  Yes.

• 1:15Chris Williamson?

  And sat down opposite me and I didn't know who it was.

• 1:17Ryan Holiday?

  Yes.

• 1:18Chris Williamson?

  And I had to try and do an episode without breaking the fourth wall that I didn't know who they were. And see if I could excavate what the fuck is going on here? Who is this psychologist, athlete, coach, trainer, like you, motherfucker? And, uh, and do it without like destroying the episode. I always thought that would be like a fun challenge.

• 1:37Ryan Holiday?

  Well, and, and the reason you challenge yourself artificially is that life doesn't really care about your plans.

• 1:44Chris Williamson?

  It's played by your rules.

• 1:45Ryan Holiday?

  So I, I had a talk I was supposed to do in Kentucky, like a couple of weeks ago. And so I was supposed to fly in. I had all day and then I would do the talk at night. And then, you know, I get to the airport at nine and it's like 30 minutes delayed, 30 minutes delayed, 30 minutes. It's starting to get crazy and some incredibly complicated, very expensive travel adjustments later. I land and I'm in the car like it's, I'm already late. So they've pushed it. They've, they've been stalling. Everyone's there. Everyone's there and I'm the last speaker and I'm, I'm, you know, I'm texting them and, and I go, okay, like I just landed. Uh, I'm, I'm 12 minutes away. I will be there. Uh, I will run up and go on and, and they, they go, "Okay, that's awesome. We're waiting for you. Where are your slides?"

• 2:30Ryan Holiday?

  And I go, "What do you mean?" Like I, I know for a fact they came in yesterday. Um, so you should definitely have them, but I'm like, here they are again. I'm like texting. Here, here's the link to the, there's the drop back links to the slides again. And they're like, "Okay, awesome." And then, uh, so, you know, they get there. Seven minutes to go. Yeah, seven. They, I opened the door, uh, the car and I'm, you know, running upstairs. I'm carrying my suitcase up, up to the thing I'm getting there. And, and then as they're miking me up, they go, "And you don't have slides, right?" It's like, is no one talking to each other? Like, now I know for a fact that you've had the slides for at least seven minutes, you know?

• 3:08Ryan Holiday?

  So, so, uh, and, and there's like a band on stage performing, uh, uh, that's stalling. Cause it's like, it's an unusual. The guy goes, "Okay, so, um, uh, the band's gonna play the first 20 seconds of Two Minutes to Midnight by Iron Maiden, and then you're up." And I go, "Okay, so we got that." Like we had a live band performing, uh, like a song that I like, but no slides. And then the guy's like, "I'll try to figure out the slides." And I go, "In the next 20 seconds? What are you talking about?" I was like, "This is, you know, this is done, man." Uh, I, I was like, "I'll just, you know." But I walk and so I start to talk and, and I'm, you know, now I've got, you know, 45 minutes of time to fill with no slides.

• 3:53Ryan Holiday?

  And you can't just do the talk you were gonna give without slides because it's, you can't be like, normally there'd be a slide. Every other minute. Yeah, exactly. And so I'm like, "What am I gonna talk about for 45 minutes?" I'm starting and then the guy's like, Trying to talk to me via the screen, you know, he's like slides are

• 4:12Chris Williamson?

  Comfort monitor.

• 4:13Ryan Holiday?

  Yeah, he's like slides, slides incoming should be about 10 minutes, you know, and it's like, this is too late, man. But, but, you know, I was able to just give some version of the talk that I've now given several times.

• 4:26Chris Williamson?

  But new, or maybe some new shit came out.

• 4:28Ryan Holiday?

  Yeah, of course. But, but, but the interesting thing is like, you think, to me, the lesson in these things is always like, you think you need it to go a certain way, you think you want it to go a certain way. And then when you were forced to do it the way that you didn't want to do it, not only do you find something out about yourself, but, but you, you actually find that the thing you were preparing not to, for it not to happen, actually isn't that bad. And it might be better in some ways. So, you know, but like you, technical difficulties are a part of any industry in life. And so if you, if you, if you, if you need it to go a certain way, you're very vulnerable. If you're good with it going effectively anyway, then you'll be all right.

• 5:13Chris Williamson?

  Yeah. What happened with that Naval Academy speech?

• 5:19Ryan Holiday?

  There's a, that was slightly different technical difficulties. So, you know, normally you send your, like, so for the last four years, I've been speaking every year to the incoming class of the Naval Academy. It's called plebes summer. So these are like the brightest kids in the country, future naval officers, so they're going to run submarines and fly F16s and command aircraft carriers. I mean, future presidents, future admirals, future heads of the CIA.

• 5:46Chris Williamson?

  Real world Top Gun shit.

• 5:47Ryan Holiday?

  These are the, these are the best, you know, most promising people in the world, actually, because the Naval Academy sometimes has like students from other countries on these sort of guest programs. So every season, every year for the last four years, I've been doing this series of lectures on the cardinal virtues of courage, discipline, justice, wisdom. So I've done courage, done discipline, I've done justice, and then I'm supposed to do wisdom this year. And So you send your slides in before, not for approval, but for technical reasons. Like you don't, you don't show up with your computer because, you know, they don't have the plug or you send them in advance. So I sent them in, you know, the night before as I had for every

• 6:26Ryan Holiday?

  subsequent talk and have had previously received zero notes because that's not what we were doing. And then I get a call, you know, I get up, I go for a run, I'm walking through the talk and I get a call from someone at the academy and they go, hey, so there's this thing in the talk that we would like you not to talk about. And of course, I knew exactly what they were referring to because I had spent a lot of time thinking about what I was going to talk about. And one of the things I felt sort of duty bound to address was they had just removed several hundred titles from the Naval Academy Library. As part of this order from the president that was supposedly about addressing,

• 7:10Ryan Holiday?

  you know, DEI and wokeness or whatever, they had removed books that talked about those themes from the library.

• 7:18Chris Williamson?

  Okay.

• 7:18Ryan Holiday?

  So you could say you have a problem with the policies, right? And the president is allowed to decide, you know, how the academy is going to be run. But you can't remove books from an elite university because you don't like what's in the books. That's a very different thing.

• 7:37Chris Williamson?

  Well, it's an interesting point there. Was it Meghan Phelps Roper that did the witch trials of J.K. Rowling? So this was the inverse of that situation. That was one book, one series of books, Harry Potter.

• 7:49Ryan Holiday?

  Yeah.

• 7:50Chris Williamson?

  Originally in the 90s and 2000s by right wing.

• 7:55Ryan Holiday?

  Yeah.

• 7:55Chris Williamson?

  Fundamentalist Christians, they campaigned to have them banned from schools because they already that it was witchcraft. And then two decades later, the left wing progressive people are trying to get it banned because they think that J.K. Rowling is a transphobe. And what you're talking about here is this is the other way around. This is right wing in the modern world, trying to get rid of books that they don't like.

• 8:15Ryan Holiday?

  Well, and, and, and this is why we don't ban books because it's stupid. And it, it's incredibly inconsistent, right? Like the Bible is a very banned book. So, so they're, they're removing it. Because these books have these objectionable themes. But of course, Mein Kampf is still in the, is still in the academy library. And, you know, so here you are removing a book that's talking about like minorities that died in the Holocaust or minorities that served in the troop. Like when you, when you have ChatGPT pull up a list of books that it thinks might be objectionable, and then you just rip them out of a library, you're in very dangerous territory.

• 8:55Ryan Holiday?

  And so I was gonna speak about this in, in, uh, because it pertains to something I've been writing and talking about there, which is that Admiral James Stockdale is one of the most famous graduates of the academy, one of the most famous modern practitioners of Stoic philosophy. After he graduates from the academy, the Navy sends him to Stanford where he gets a, a post grad degree and he studies quite a bit of philosophy there. And his favorite course while he's at Stanford, this is in 62 or 63, is he takes a course on Marxist thought and they only read the primary Marxist texts. So not like commentary on Marx, not neo Marxism, but like Marx himself and Lenin.

• 9:37Ryan Holiday?

  And they read and they, they spend an entire semester talking about what the Marxists, Marxists thought. And you might go, well, what does a Navy fighter pilot need to learn about Marx? Well, when he ends up in a Marxist prison camp in North Vietnam, is subjected to years of brainwashing and torture and propaganda, it actually comes in extremely handy. And he would talk about how he was able to go back and forth with his captors. And then in many cases, he knew Marxism better than they did. And that this was a defense mechanism, right? And it's actually funny as the Stoics talk about this too, which of course I was gonna talk about in the talk. The Stoics, Seneca talks about reading like a spy in the enemy's camp. The idea is you, I'm gonna stop.

• 10:22Ryan Holiday?

  No. Oh, no, no, I just heard this. Oh, good. Good. So the, the idea is that you, you wanna know what your opponents think. And in this case, we're not even talking about opponents because we're talking about, you know, the memoirs of Maya Angelou that are getting removed from the, the, the library of a, again, a university on par with Harvard or Yale or West Point. So I was gonna talk about why this is, this is why we can't be afraid of ideas. And in fact, we have to engage with ideas that we disagree with and dislike.

• 10:53Ryan Holiday?

  Well, you can imagine the people that are removing, once the leadership of the academy had put themselves in the position of not challenging the order and, you know, sort of removing the books without protest, they're now in a tricky situation of like, can we allow criticism of this decision, right? This is what happens when you, and of course Stockdale talks about this too. He talks about when you start to make compromises with extortionists, you have to make more and more compromises and then pretty soon you're not just removing one or two books because it's controversial, but then you're revoking invitations to speak from people who are criticizing that idea. And it escalated.

• 11:32Ryan Holiday?

  So, so they, they, they asked me to remove it and it's like, I can't, I felt, and I don't know if I could have made this decision early on in my life, but I talked to these kids who are gonna, again, in the future be entrusted with nuclear weapons and immensely powerful bits of machinery and budgets of the billions and billions of dollars, that I can't give them a lecture about courage, I can't give them a lecture about discipline, I can't give them a lecture about ethics and doing the right thing. And then when someone says, hey, if you want to keep talking here, we'd like you not to speak about the things that we're trying to sweep under the rug. And so I said, you know, I can't do that.

• 12:13Ryan Holiday?

  And so, of course, the invitation was revoked and then so was the subsequent invitation. The interesting thing about, to me, was I, I said, you know, I think you think this will avoid controversy, but it's only going to do the opposite. Not only is it going to do the opposite because like this is a public, like not, this is a, a publicized event that is now ended, you know, 10 minutes before it's supposed to go on, but, you know, part of the, like I was speaking, the-

• 12:48Ryan Holiday?

  I was speaking at, it was brought there by this center on campus called the Stockdale Center for Ethical Leadership. So the irony of like, let's remove books that we find to be objectionable and then let's not talk about it. And then let's pressure a person from the center of ethical leadership. You know, the ironies are stacking up here. But like, there is this, there is this presumption that people in the military are just like big, tough, strong, you know, robots that you send in to do, but that's, that's what gets countries and the world into trouble. Like the crown jewel of the American military and the Western militaries for centuries

• 13:32Ryan Holiday?

  has been the ability of their leaders to think, to challenge orders and to question, right? This isn't to say that it's anarchy, but like you need independent thinkers or everyone's thinking the same thing and thus not thinking at all. And so like, you are going to want these young men and women at some point, when they're entrusted with leadership and power, to make difficult unpopular decisions that are, you know, maybe not always in their, the interests of their careers. And what this leadership is showing them in this moment is, we might say that, but

• 14:17Ryan Holiday?

  we don't mean it. Right? Like, like imagine you become a multi-star admiral of the Naval Academy, one of the, you know, crowns, and then you're not just a party to removing books from the library, but then you are, like, what, I guess this, this is a theme that I've been writing about for these last couple of years is like, what is the point of power, influence, success, a platform if you don't? Use it. And so it was a strange, real experience. It's only sort of gotten worse. Like the West Point just revoked an invitation and an award they were going to give to Tom Hanks this week because of his political views.

• 15:00Ryan Holiday?

  So we are in this full sway of like the pendulum of cancel culture, snowflake-ism has gone from like this way to this way.

• 15:11Chris Williamson?

  And it's the same thing that's happening just in the opposite direction.

• 15:14Ryan Holiday?

  Yeah, and it's equally stupid in both directions and it doesn't help anyone. And then, you know, it was funny because people kept going like, well, what about this book? And what about this book? You know, this is a bad. And I go, I don't know the names of basically any of the books. Like, I don't give a shit what the names of the books are. I'm actually sure most of the books are bad. Like, the library has hundreds of thousands of titles. It would make sense that, in fact, a large percentage of them are bad. I would agree that most books that are published are bad and stupid and wrong. Like, that's how it works. But a free society, you know, requires the free transmission and publication of ideas. Right?

• 15:59Ryan Holiday?

  And so it's a weird moment in time, to be sure.

• 16:02Chris Williamson?

  You've been in the war zone, it seems.

• 16:04Ryan Holiday?

  Well, no. As I did, maybe an intellectual war zone. I think what's ironic about it is these are people who are going to at some day be sent into a real war zone and we're nervous that they're going to read Maya Angelou or even the most like offensive, stupid, wrong, you know, ass-backwards book and just be like, immediate.

• 16:30Chris Williamson?

  That's my worldview now.

• 16:31Ryan Holiday?

  Yeah, their mind melts. So like, actually, this is when we would want to find that out, you know?

• 16:36Chris Williamson?

  Ah, okay. So read these stupid books, see if your mind has changed, and if so, out you go.

• 16:41Ryan Holiday?

  Yes, exactly.

• 16:42Chris Williamson?

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• 18:11Ryan Holiday?

  It's the hardest to define. I think courage is something we know it when we see it. You know, discipline, pretty straightforward. I think the thing about wisdom is that

• 18:22Ryan Holiday?

  it's not just elusive in terms of its ineffability, like it's hard to define. You know, it's experience, it's knowledge, it's intelligence, it's creativity, it's insight, it's perspective, it's all these things, right? But the interesting thing about wisdom is that it's one of those ones that if you think you have it, you almost certainly don't. And the second you think you have it,

• 18:51Ryan Holiday?

  you find that there is more left for you to learn. So there's something elusive about it in the sense that the horizon is elusive, right? Like you approach it and you feel like you're not making progress. You look behind you and you clearly have made a lot of progress. Look at all the things that you've read. Look at all the things that you've learned. Look at how much smarter you are than you were before. And look how far away the people who were standing with you when you began are. But, but there remains an infinite amount still to know. And so there is something. Inherently humbling about it, the physicist John Wheeler said, you know, as the island of knowledge grows, so does the shoreline of ignorance. I think that's, that is the paradox of wisdom, that the, the more you learn,

• 19:35Ryan Holiday?

  not just are you humbled, in that most, you know, really smart people are actually quite humble. But, but the more you learn, the more you learn about all the things that you still want to learn about.

• 19:48Chris Williamson?

  Hmm. What do most people get wrong when they think about wisdom, where it comes from?

• 19:54Ryan Holiday?

  Well, you know, like there's some, you know, is it, is it, is it like book smarts or street smarts? Like, is it school or is it life? As if it's this binary thing. Of course, it's a combination of all of the above. It's like, you want a base of, of knowledge. Ideally, you want to learn from all of the experiences, all the, the, the great ideas that humanity has come up with over thousands of years. And then you have to go out and experience things. And then what that does is it informs what you've learned. And then the things that you continue to learn inform the experiences you're having.

• 20:38Ryan Holiday?

  So the subtitle of the book is like, learn, apply, repeat. And that's the idea is that, is that it's this loop of always be learning, always be exposing yourself to things, and then always be going out and applying and trying the ideas. So, you know, if you're just sort of reading up in your, your tower, so to speak, you might be getting smarter, but I wouldn't say you're getting wiser. And then there, there is something fundamentally stupid, though, about trying to learn all these lessons yourself, right? Like, you go, I think, I think it was Otto von Bismarck, you know, he said, any fool can learn by experience. I prefer to learn from the experiences of others. So.

• 21:21Ryan Holiday?

  Why, why would you want to figure something out when someone has been in your exact position before and not just learned from it, but like written about it? And then other people have written about them. And, and so you think about like this position you're trying, this, this thing you're going for, this thing you're attempting, like some of the smartest people who've ever lived have, have spent years of their life thinking about just that thing. And then, and then there is the ego in us that goes like, well, I'll wing it, you know, or, or I, I know better. And, and so the reason that humility is this key to wisdom is not just like you can't

• 22:06Ryan Holiday?

  learn that which you think you already know, but, but it, it, it keeps you hungry to learn more and more.

• 22:16Chris Williamson?

  I have this idea about unteachable lessons.

• 22:18Ryan Holiday?

  Yeah.

• 22:19Chris Williamson?

  And it's a, a unique category where no matter how many songs and movies and stories from your grandparents and warnings, you cannot expedite the process of understanding this thing through somebody else's story tale. You can only learn these things. Money won't make you happy. Fame won't fill your self-worth. That girl's not lovable. She's just hot and difficult to get. You should see your parents more. You should work less hard, you know? These things that are cliche and the reason that they're cliche is that they seem to be

• 22:54Chris Williamson?

  so reliably groundbreaking to everybody when they arrive there. So it almost becomes its own, it's like a self-defeating prophecy that everybody says it, which means everybody thinks that they know it, which means everybody discounts it as like, oh, that's just like a wives tale. That's not like you shouldn't put your hand on a hot stove. That's, these people, they've just accepted it as, as part of the source code of reality. But I watch me dance through this minefield and I'll do pirouettes and I'll spin around. The rules won't apply to me.

• 23:28Ryan Holiday?

  But the funny thing about that is, I think one of the reasons those lessons are so cliche, and then why you talk about them so much, is partly because, okay, so you take something like, money won't make you happy, or fame is empty, or you're not going to fill that hole in your soul by achieving and doing.

• 23:50Ryan Holiday?

  That's a theme in literature and art and, of course, social psychology also. And there's probably some evolutionary reasons why that's a hard lesson to learn, right? This is what propels humanity forward. But some of us learn that lesson sooner than others, right? Some people have to go as far as Alexander, like literally to the end of the worlds to learn it, and then other people experience it during their college graduation.

• 24:20Chris Williamson?

  What was Alexander's realization around that point?

• 24:22Ryan Holiday?

  Well, I'm just saying Alexander gets all the way to the end of the world, and his men are like, how much longer are we going to do this? And he says, you know, let it be said that you turned around here and didn't conquer the rest of the world with Alexander. And then he subsequently dies. And he dies this brutal, painful death where some of the theories are like, he was like, sort of in this conscious coma where he's like frozen. But like, it was, it was a, let's say it was an end where he might have had a few moments to contemplate whether it had all been worth it, right? And so my point is, you can learn it at the very far end of the extremes, or you can hear it at the first inkling of it.

• 25:04Ryan Holiday?

  Like, I've said before, like, I feel like life is always trying to tell us something. And eventually, it will tell us in a way that we can hear it. And so-

• 25:13Chris Williamson?

  The whispers just get louder and louder.

• 25:15Ryan Holiday?

  Yeah, do you want to hear it, do you want to hear it when, when life is whispering this to you? Or do you want life to have to pin you down and scream it in your face, you know? Like, in sobriety circles, they talk about, like, you know, hitting rock bottom while you still have two cars in the garage. Like, do you have to hit rock bottom when you've blown up your entire life and lost everything and everyone? Or can you take this DUI as a sign? Right?

• 25:40Chris Williamson?

  That's a really, a really great point that, um, yes, these lessons are unteachable, but some people need to be taught more times than others.

• 25:46Ryan Holiday?

  Yes, and, and, and that was, you know, the Romans talked about, you know, the, the fool is not someone who, who stubs their toe on a rock. It's the person who stubs their toe on the same rock more than once. And so it's how quick can you learn the lesson? And so part of, part of why you, you take in, especially early on, why these classic myths and ideas and the Western canon is so important is that they contain, from the Bible to the Odyssey, uh, you know, Demarques Aurelius and Aristotle and, and, and all the great stories, is they contain kind of the sum total of human wisdom.

• 26:23Chris Williamson?

  Hmm.

• 26:23Ryan Holiday?

  Right? And some of them though, you don't learn, you, you hear, but you don't understand until you have the experience that matches that lesson.

• 26:32Chris Williamson?

  Oh, that's that thing.

• 26:33Ryan Holiday?

  Yes. And, and so you need to, you need to, you, you need to have the ideas to match with the experiences. Neither is, is, is sufficient on its own.

• 26:46Chris Williamson?

  I love that, that blending of the two, especially because if you don't have a, a good enough framework, sort of a robust scaffolding to hold your life's experiences on. Yeah, maybe you will take the right lesson, but maybe you'll take the wrong one. Maybe you get gold medalist syndrome. You think, ah, two.

• 27:05Ryan Holiday?

  Yes.

• 27:06Chris Williamson?

  Two, that's the issue. The issue is I need to prove that I wasn't lucky, that I was good.

• 27:10Ryan Holiday?

  Yes.

• 27:10Chris Williamson?

  I don't just sell the one company for a hundred million dollars. I've got to run it back again.

• 27:14Ryan Holiday?

  Yeah.

• 27:14Chris Williamson?

  In a different industry and then the thing, as opposed to, no, this is a situation, you have learned this before. It's the exact same gremlin, just coming at you from a slightly more conniving angle.

• 27:26Ryan Holiday?

  Yes. Um, and, and it's to be able to recognize, oh, this is what so and so was doing here. This is so and so at this, you know, critical juncture point like, and, and there was a time when we had enough shared story that, first off, there were just fewer stories. So everyone could kind of recognize, oh, this is like, you know, Odysseus at the sirens, or this is Hamlet, or this, this. This is, this is, you know, George Washington at this moment, you know, you have these stories that are designed to teach these moral lessons. Like, the greatest biographer of all time is Plutarch. And Plutarch says, you know, there's a difference between biography and lives. And he says, I write lives and lives are illustrated by a certain anecdote,

• 28:09Ryan Holiday?

  a little story, an utterance of a few words that help you unlock the lesson or the fatal flaw or the brilliant genius of this person. And, and so when you read about these historical figures, who are often flawed and tragic figures, the idea is you take back from them little lessons that then, yeah, when you're winning a gold medal or you just sold a company or, you know, you're, you're about to gamble it all on this thing that you believe is, you know, the key to unlocking your happiness or your legacy or whatever, you go, oh,

• 28:51Ryan Holiday?

  maybe I should ask myself, am I about to do what they did? And how did it go for them? And, and so it's having this broad array of case studies and stories that were, you know, not always the most historically accurate, but they were illustrating something about the human experience that we need to remember.

• 29:12Chris Williamson?

  Mm hmm. I was spending time with an impressionist a couple of weeks ago.

• 29:17Ryan Holiday?

  Like a comedian?

• 29:18Chris Williamson?

  Yeah, yeah, yeah.

• 29:19Ryan Holiday?

  Or do you mean a painter?

• 29:20Chris Williamson?

  No, sorry. Yeah, good, good. He does impressions, whatever that person's called.

• 29:24Ryan Holiday?

  Yeah.

• 29:24Chris Williamson?

  They both called the same thing.

• 29:25Ryan Holiday?

  I think so.

• 29:26Chris Williamson?

  Someone should change it.

• 29:27Ryan Holiday?

  Yeah.

• 29:28Chris Williamson?

  Anyway, and I was explaining, I've got Matthew McConaughey coming back on the show.

• 29:31Ryan Holiday?

  Yeah.

• 29:31Chris Williamson?

  Wouldn't that be exciting? And he's like, what was it like to sit down with him the first time? And I said, all of the thing, he's very charismatic and all the rest of it. And he does a great McConaughey. And I said, he does this thing that you didn't do when you did it. And he doesn't ever have, it seems to me like he doesn't have stuff in his mouth, but he goes like.

• 29:50Chris Williamson?

  He's sort of like, as if there's a little bit of straw or something that he needs, and he does this with his hand. And the dude was like, that's the unlock. And he explained to me that in the art of doing impressions of people, there is a, an unlock, and the unlock is this one thing, the way that you speak, the pronunciation of the S, the moving of the fingers, the hands, the face, whatever. He says, that's the thing that people hook on to. In the same way as what you're talking about here is that there are these portable stories, as Clay Habits calls them, these individual, maybe even a tiny little aphorism, three-word aphorism, whatever. And you go, that's the thing. And both me and you quote other people a good bit, because

• 30:36Chris Williamson?

  original thinking's pretty tough. And also, people way smarter than me and you have already figured stuff out. And it's kind of our job to

• 30:43Ryan Holiday?

  Sure.

• 30:43Chris Williamson?

  essentialize that and make it accessible.

• 30:45Ryan Holiday?

  If I could say it better, I would.

• 30:47Chris Williamson?

  Yeah, true. And I've tried. And I think that, you know, in many ways, for me, the reason that I love it is that using small quotes, aphorisms, mantras, stuff like that, is kind of like a Winzip file that condenses down this big thing. My memory's not that good, but it's not bad if I just have to remember this small sequence.

• 31:08Ryan Holiday?

  Sure.

• 31:08Chris Williamson?

  And I go, oh, yeah. The universe has changed and life is but what we deem it. Oh, well, there's like this big thing that that means that I kind of remember a bit.

• 31:19Ryan Holiday?

  Yes.

• 31:19Chris Williamson?

  But I can recall this. I can remember the chorus. And from that, I kind of, the rest of the album comes along with it, too.

• 31:25Ryan Holiday?

  Yeah. And, and I think too many people have confused, you know, history and trivia. Exactly what year this happened, exactly how the name is pronounced, you know, exactly, you know,

• 31:41Ryan Holiday?

  Where the troops were aligned in this battle or that battle, you know, is is much less important as as to the the why or the characters or the kind of the the fundamental moral lessons uh that that thing has the opportunity to to teach us. And that's what the classics and the sort of ancient stories have always been. Like Cincinnatus, do you know the story of Cincinnatus? So Cincinnatus is this Roman general who's living in retirement. This this story will will sound familiar to you in a second. He's this famous Roman general living in retirement. And the Roman army is in battle in some distant land. And basically, the whole of the Roman army is is uh is trapped. And so Rome is basically undefended.

• 32:25Ryan Holiday?

  And so the the Roman elders go to Cincinnatus, who is plowing on his farm in retirement, and say, we we need you to save Rome, uh and we will make you dictator. And so he's made dictator. He leads a a small, you know, troop of Roman uh Roman auxiliaries and, you know, frees the Roman army, saves Rome,

• 32:49Ryan Holiday?

  and is now dictator. And he, after seventeen days, resigns the dictatorship and returns to his farm. Right? This is the plot of Gladiator, of course. And it's also the model for George Washington resigning his commission after the Revolutionary War. You know, uh, when King George hears that that uh Washington is going to return to his farm, he goes, if he does that, he'll be the greatest man in the world. Both of them understand that this is an allusion to the example of Cincinnatus when when Washington resigns the presidency after two terms. It's again Cincinnatus that he's. So this is a famous story. But Cincinnatus almost certainly did not exist.

• 33:34Ryan Holiday?

  Like, that is a story that goes back so far in Roman history that there is almost no factual basis for it, that anyone can clearly point to one way or another. But the story has existed for so long that the Romans certainly thought it was true, and Washington thought it was true. And King George thought it was true. And you know, when I tell it to my seven year old, it may as well be true. And I think some people have taken the role of the historian to prove that it didn't happen. To be like, here, George Washington didn't chop down the cherry tree. Or, you know, Cincinnati didn't really exist, or this didn't happen, or it was more complicated than that. And look, if you're a grad student specializing in that thing, perhaps that is important.

• 34:18Ryan Holiday?

  But for most people, most of the time, the the significance of that is the the lesson of sort of restraint and selflessness that that that actually power can be laid down. And that, you know, the truly great and powerful people not only do do that, but that's the gift they are giving the future generations, this continuing this tradition of the peaceful transfer of power. And so the the history is supposed to be the sort of sacred, hard earned knowledge that we pass on from person to person. And so a lot of this famous stories, you know, maybe they're true, maybe they're not.

• 35:04Ryan Holiday?

  If if you're being literal about them, you're missing the point.

• 35:07Chris Williamson?

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• 35:52Chris Williamson?

  Just go to the link in the description below or head to functionhealth.com/modernwisdom. That's functionhealth.com/modernwisdom.

• 36:01Chris Williamson?

  Did you read Derek Sivers' book Useful Not True?

• 36:04Ryan Holiday?

  No.

• 36:04Chris Williamson?

  Okay, so I had this idea for, I swear to God, I came up with it independently, which was figuratively true, literally false.

• 36:12Ryan Holiday?

  Yes.

• 36:13Chris Williamson?

  Literally true, figuratively false.

• 36:15Ryan Holiday?

  Yes.

• 36:15Chris Williamson?

  And Derek came up with something that was not too dissimilar, which is usually a good idea.

• 36:19Ryan Holiday?

  Yeah.

• 36:19Chris Williamson?

  It's like, hey, two people pointed at the same thing from different angles, like,

• 36:22Ryan Holiday?

  Yeah.

• 36:22Chris Williamson?

  there might be something here.

• 36:24Ryan Holiday?

  Sure.

• 36:24Chris Williamson?

  Um, literally true, figuratively false. Uh, you, uh, determinism might be a way to look at this, that perhaps there is no free will and the entire way that we move through the world is predetermined by the Big Bang and the dominoes just falling, falling, falling. However, functionally.

• 36:43Ryan Holiday?

  What would you do with that?

• 36:44Chris Williamson?

  It's fucking useless. It makes me nihilistic. It makes me feel like I, I don't have any control of my future. Something which is literally false but functionally true.

• 36:53Chris Williamson?

  Um, in the Middle East, in sort of medieval times, pigs are morally dirty creatures. They're no more or less moral than any other creature. But in a hot climate, their flesh contains more pathogens on average.

• 37:07Ryan Holiday?

  Sure.

• 37:08Chris Williamson?

  So not eating them, probably a pretty good idea. Porcupines can throw their quills. No, they can't. They can't fucking throw their quills. But if you treat it like it can, you stay just a little bit further clear and you're less likely to get stung. So this idea that holding modern stories to the standards of objective rationality, where does it appear on the spreadsheet? Please show me how this comes into land. Uh, I think for a lot, it was a good solvent that was supposed to kind of wash away a lot of bullshit that existed, because there was stuff that was literally false, functionally false, and that actually needed to fuck off.

• 37:49Ryan Holiday?

  You know, there's an expression that, that traditions are often solutions to problems that we've forgotten about and. This idea, there's kind of been this fetishization these days of like thinking from first principles, right? And this is important.

• 38:04Chris Williamson?

  I'll arrive at it myself.

• 38:06Ryan Holiday?

  Yeah, I think for myself, I'm a first principles thinker. I.

• 38:11Chris Williamson?

  Not one of the sheeple, I'm autonomous.

• 38:13Ryan Holiday?

  Yeah, I don't care about your precedent. And, you know, a lot of precedent is hard won, right? And, and maybe even why it was hard won, or how it was hard won, you are blowing past and you are ignoring why it was set up this way in the first place. And so not only is it exhausting and unsustainable to truly think, you know, from first principles and everything, but yeah, sometimes things are incidentally solving one problem and also solving another problem, where things are, variables are, are hopelessly tied up with each other. So you, you, you go, hey, we don't need this. This is stupid. And you don't understand because you don't have 20 years, or 50 years, or a thousand

• 38:57Ryan Holiday?

  years of experience in this thing, that actually this is a subpar solution, or an elegant solution to a very complicated or, or multifaceted thing. And so the arrogance, I think that again, what wisdom is, is this humility of having done hard things before and solved hard problems before. And you go, oh, okay, it's, it's probably not going to be solved like this. And this thing that popped into my head that should magically resolve all of this, you know, is, is naive. Like, do you know the story of the Gordian knot?

• 39:32Chris Williamson?

  No.

• 39:32Ryan Holiday?

  So there's this knot that's tied, that is impossible to untie, and person after person goes to untie it. And if you, if you untie it, you know, you become the king of this land. And I think it's Alexander comes and. And, um, you know, he, he, he solves the Gordian knot by chopping it in half with his sword. And, um, yes, that's technically a solution, but it's also not a solution. You haven't actually untied the knot. Um, and, and so, so there is this, again, this sort of fetishizing of like these complete solutions to things that, hey, the, the people before were not idiots.

• 40:11Ryan Holiday?

  And in fact, they had a little more humility than you did and understood that there probably was not a solution that, that pleased everyone or, or checked every box. And so that's why this is where it is and why, by the way, things have remained relatively stable for a long time. I think we're seeing this now in politics, but also life where, okay, if you're a Silicon Valley investor and you invest $50,000 in a company, um, okay, the downside of you being wrong is that you lose $50,000, but the upside is you might make $5 billion. So that's great in this very specific domain that you are in,

• 40:54Ryan Holiday?

  where you get access to lots of early stage companies. You have a large, broad base of capital and you can throw, you can be wrong a lot to be right one time. Well, most of life is not like that, right? And politics and life geopolitics are not like that.

• 41:10Chris Williamson?

  You don't get to be wrong that much before there's a catastrophic outcome.

• 41:13Ryan Holiday?

  Yes, yes. Um, and so a lot of the systems that we have set up and a lot of the procedures we have, this is not just in America, but all over the world, talking about the UN or the EU or all these different institutions. They are there not to create the easiest, most well-functioning, efficient machine in the world. They're there to make sure World War III doesn't happen. They're there to make sure that a nuclear weapon doesn't explode. They're, you know, they're there to prevent, uh, an economic meltdown, right? They're protecting against downside, which unlike, say, investing is not you lose the capital that you put in. The downside is you lose everything for everyone forever.

• 41:56Ryan Holiday?

  And so understanding what environment you're in and the stakes, this is also, I think, something that some really smart people. Don't have, and in fact, they've learned a lot of bad habits from being the master of one domain. Like, some domain expertise is transferable, and a lot of it is not. And, and the wisdom is knowing what domain expertise is transferable and what isn't.

• 42:23Chris Williamson?

  You write fantastic songs, wonderful lyricist, great at melodies.

• 42:29Ryan Holiday?

  Yeah.

• 42:30Chris Williamson?

  Don't care what you think about climate change. Don't care what you think about the Ukraine. Don't care, like, you're, that is not an area that your expertise can go to. Now, you can outsource that to other people, or you can become an expert in your own right.

• 42:42Ryan Holiday?

  Yeah.

• 42:43Chris Williamson?

  But just because you're great at this one thing.

• 42:45Ryan Holiday?

  Yeah.

• 42:45Chris Williamson?

  And so I, I agree, but as with most things, uh, the devil is in the details.

• 42:51Ryan Holiday?

  Sure.

• 42:52Chris Williamson?

  Here. So, for instance,

• 42:55Chris Williamson?

  there are people from outside of an industry.

• 42:58Ryan Holiday?

  Yes.

• 42:59Chris Williamson?

  That get a new perspective because of the fact that they're alien to this thing.

• 43:04Ryan Holiday?

  Yeah.

• 43:04Chris Williamson?

  Because they see something with a fresh set of eyes that nobody else would. And the Wright Brothers kind of strike me as a pretty canonical example of someone like this.

• 43:14Ryan Holiday?

  Sure.

• 43:14Chris Williamson?

  So I think balancing this Chesterton's fence-pilled, okay, let's be careful with what we get rid of.

• 43:21Ryan Holiday?

  Yeah.

• 43:21Chris Williamson?

  You know, which is a much more sort of conservative, less innovative, less move, fast-break things position with, well, you know, sometimes we need like a great man or great woman to come and kind of do a thing.

• 43:32Ryan Holiday?

  Yeah.

• 43:33Chris Williamson?

  And balancing those two, the innovation desire with the iteration desire.

• 43:38Ryan Holiday?

  But, but what you find in the best of those people, the Wright Brothers being a classic example of this, is there wasn't this sense that everyone else trying to tackle the flight problem. And it was a problem other people, like, people have been interested in it for thousands of years, but, you know, like, all the armies of the world were also rushing to try to figure this out at the same time. You know, there wasn't this sense that everyone else is a moron and we're geniuses. What the Wright Brothers had was this curiosity, this sort of openness to how am I working? They spend hours and hours just studying how birds, you know? Fly, they had a scrappiness to them. They were outsiders. They were independent.

• 44:22Ryan Holiday?

  But you know, the first thing the Wright brothers do is write to the Smithsonian for like every book ever published on flight. It wasn't like burn it all down. Everyone's a moron. And in fact, they would have loved to collaborate with the powers that be and would have loved to be brought in as part of it. So I, there's this tendency to celebrate the sort of brash, you know, domineering outsider who comes in and tears everything apart. But I, I think you tend to find that the, the most effective reformers have a profound understanding of why things are the way that they are. So, so that is, that's actually, you know,

• 45:05Ryan Holiday?

  the negative capability to go like, here's what I know and here's what I think is true. And here's what I understand as an outsider. And then here I've done a profound deep dive as to why it is this way. Like one of the most profound, like I'll give you two sort of related reformers. You have Abraham Lincoln and then you have Thomas Clarkson, the two basically forerunners of, of the abolitionist movement. Thomas Clarkson in the UK leads to the, the eradication of the slave trade and then slavery in England. And then, then Abraham Lincoln ends it in the United States. Both of them start their campaigns against slavery. They had this

• 45:46Ryan Holiday?

  as, as outsiders or as just human beings, this immediate impulse that slavery is wrong, that, that it doesn't matter that we've been doing it for thousands of years. It doesn't matter that, you know, billions of dollars are riding on it. It doesn't matter that all the religious teachers say it's okay. None of that matters. They understood it was wrong. That's your classic sort of outsider view, seeing the world from a new perspective. But then what they both do is they go, I gotta figure this out. Like Abraham Lincoln goes to the State House Library in Illinois and then the Library of Congress when he's a congressman. And he goes and he actually reads like what the founders said about slavery. And he realizes that the sort of dominant view at this time, that the founders were out to

• 46:31Ryan Holiday?

  preserve and protect slavery actually wasn't true. Thomas Clarkson, his genius is

• 46:37Ryan Holiday?

  He realizes that slavery is actually just like bad as a business. Like, he studies the insurance claims that slave traders are making on the human cargo that they are transporting. He's looking at the fact that like 20% of the sailors are dying on each voyage. He's actually going and looking at what a slave ship looks like. And then he draws this famous diagram that like illustrates the vividness of of what was an abstract problem before. So the point is, it's not that you have to absorb the dominant view or the status quo, but you have to understand the logic of why it is that way.

• 47:21Ryan Holiday?

  This is where justice and wisdom are interrelated virtues. Like, it's not just, oh, I have this opinion, I'm morally correct, so therefore the world should agree. You have to have this curiosity to go, well, well, these people probably aren't wrong on purpose. So why do they think this? What are the underlying conditions or incentives that are making them think this way? You know, Lincoln, a lot of people have tried to go, well, you know, Lincoln is equivocating on slavery because, you know, he was so understanding of the South. But no, that's what empathy is. He says, you know, like, we are just what they would be. We are just, they are just what we would be in their, in, if we were in their condition. Meaning, he's like, if you were raised in the South and this is what you were taught from day one, you would think about it this way.

• 48:04Ryan Holiday?

  And so what, what you have to have the negative capability to understand, and for people that don't know, that's a thing that Keats talked about, the ability to have mutually exclusive ideas in your head at the same time, or contradictory ideas. You have to be able to go, here's what they think, and here's why they think it. That's not going to change what I know to be true, or that's not going to change the fact that that's still fundamentally incorrect. But I have the ability to understand why it is that way. And that is usually a prerequisite to doing anything about it or doing anything about it effectively. Like Elon Musk is right, the federal government is very inefficient.

• 48:48Ryan Holiday?

  And he has a lot of domain expertise in his specific areas. But most people predicted Doge would fail because it would run up into these sort of longstanding obstacles and difficulties that I think he thought he could overwhelm with sheer force.

• 49:05Chris Williamson?

  Do you know Sam Korkos from Levels?

• 49:07Ryan Holiday?

  No.

• 49:08Chris Williamson?

  You know, Levels, it's like a glucose monitor thing?

• 49:10Ryan Holiday?

  Oh, yeah, yeah, I know Levels.

• 49:11Chris Williamson?

  So he was the founder of Levels. He is now the CIO of the Treasury Department.

• 49:17Ryan Holiday?

  Yeah.

• 49:18Chris Williamson?

  I'm interviewing him on Thursday. We got an episode with him on Thursday. The first long form conversation anybody from Doge has been permitted to have, and it's been like, it's okay to happen. And this is one of the kind of the fundamental questions, which is how tied up in bureaucratic red tape fuckery is the inside of the government when it comes to trying to make things more efficient? And how much can you take the Silicon Valley mindset of Notion templates and Slack and if this, then that Zapier fucking integrations? How much can you Zapier integrate your way through like vibe code? How much can you vibe code?

• 49:56Ryan Holiday?

  Yeah.

• 49:57Chris Williamson?

  The government into efficiency?

• 49:58Ryan Holiday?

  Yeah.

• 49:59Chris Williamson?

  And how much of it is this ossified walnut shelved mahogany leather fucking Chesterfield sofa bullshit that's getting in the way? And I think that's gonna be.

• 50:08Ryan Holiday?

  And then, and then how much of it is there because that is the best solution to an imperfect situation? And do you have this humility and the openness and the empathy to understand that that's why it is that way?

• 50:29Chris Williamson?

  Does that suggest that along with wisdom comes a humble comportment could sort of gets brought in for the ride as well? That an amount of humility grows with the more that you are wise?

• 50:46Ryan Holiday?

  I think so. I think so. Um, you know.

• 50:51Ryan Holiday?

  Epictetus said, "One of the signs that you're making progress in the path to wisdom is that you get in fewer arguments." And I don't think that means that you, you know, just roll over all the time. Or that you, you know, you have no core values. It's just you understand, "Well, this is why they think what they think." You know, as I get older, I have, I certainly do have fewer opinions about shit that I don't think actually matters, right? I have, I have fewer opinions as I get older about other people's opinions, right? Because they're right. They like that, you know? And I'm spending a lot of my energy trying to explain why they shouldn't like that,

• 51:35Ryan Holiday?

  as if it changes or means anything. And so, part, Stoicism was this idea of getting to a smooth flow of life. Right now, you can get to a smooth flow of life by removing yourself from most of the contentious and complicated parts of life, right? You can have a smooth flow of life if you live on an island in the middle of the Pacific and you don't work, right? Like, you never have to worry about money, you're not trying to do anything, you're not trying to accomplish anything, you don't care about anything. It's pretty easy to live on vibes. Can you get to a smooth flow of life in the arena, right? As you're trying to accomplish and do and contribute?

• 52:15Chris Williamson?

  The same as you can do your live talk with a fully scripted out comfort monitor in front of you and slides behind you. Can you do it when there's no presentation and you've just got off a plane 12 minutes ago?

• 52:28Ryan Holiday?

  Well, you can have, if it always goes that way, you'll be fine. But it's not always gonna go that way.

• 52:33Chris Williamson?

  Kind of fragility associated with that.

• 52:34Ryan Holiday?

  Yes, yes. And so resilience, adaptability, you know, being able to function and contribute and perform is the ability to, to work in less than ideal environments with less than ideal people. And, and that's, I think, a skill you cultivate and develop over time.

• 52:53Chris Williamson?

  We'll get back to talking in just a minute, but first, some things are built for summer. Sunburns, hot girl walks, your ex posting their Euro road trip, and now, lemonade and salt. Uh, Element just dropped their brand new lemonade salt flavor and it's everything that you want on a hot day. Tart, salty and stupidly refreshing. It's like a grown up lemonade stand in a stick with actual function behind the flavor. Because, let's be real, if you're sweating through workouts, sauna sessions, or just walking to your car in July, then you are losing more than just water. Element replaces the electrolytes that your body actually needs. Sodium, potassium and magnesium with no sugar, no junk and no nonsense. I've been drinking it every single day for years and in the Texas heat, this lemonade flavor in a cold glass of water is unbelievably good. Best of all, they've

• 53:38Chris Williamson?

  got a no questions asked refund policy with an unlimited duration. So you can buy it and try it for as long as you want. And if you don't like it for any reason, they'll give you your money back. You don't even need to return the box. That's how confident they are that you'll love it. Plus, they offer free shipping in the US. Right now, you can get a free sample pack of Element's most popular flavors with your first purchase by going to the link in the description below or heading to drinklmnt.com/ModernWisdom. That's drinklmnt.com/ModernWisdom. Given that we've got modern culture of shortcuts, life hacks, how do you convince people that uh, wisdom is worth a long, uncomfortable path?

• 54:18Ryan Holiday?

  The thing is, at some point in your life, you're gonna need it, right? You're gonna come to some vexing decision, some challenging moment, you're gonna go through something, you're gonna be in the middle of something. And in that moment, uh, you're gonna wanna have wisdom to draw on, right? Wisdom that needed to be accumulated a long time ago. It will be too late in that moment for you to do the crash course, to figure out all the things that you need to do, to develop the meta skills you need to solve this problem in front of you. Um, and so, are you doing the work now? To me, that's the question. I, I think, one of the things we can all agree about wisdom is that it's

• 55:00Ryan Holiday?

  not something you're born with. There are certainly people who are wiser than others, but I don't think any of them came out of the womb that way.

• 55:06Chris Williamson?

  Which is what distinguishes it from something like raw intelligence.

• 55:10Ryan Holiday?

  Yes.

• 55:10Chris Williamson?

  Compute power.

• 55:11Ryan Holiday?

  Yeah. Wisdom is something you accumulate over time. And so, if you're gonna wanna draw on it in the future, what are the deposits you're making now? So that, that's the investment. That you make in wisdom. There's a story Seneca tells us, and I think it goes to this very idea of hacks and shortcuts and the fetishizing of like gurus and teachers who can just tell you everything you need to know. Watch this video and you know, I'll tell you everything you need to know, or you know, come to this seminar. He talks about this this Roman who wanted to be seen as smart. And so, you know, the Roman could have gone to classes, the Roman could have read hundreds of books, the Roman could have experienced

• 55:55Ryan Holiday?

  things. And instead, this guy acquires a number of wealthy slaves, or sorry, this wealthy Roman acquires a number of very literate slaves, each one like an expert on a different topic. And at dinner parties, they would, you know, whisper in his ear the things that he needs to know. And so everyone kind of thinks he's very smart. And the guy thinks he's getting away with it. He thinks he's figured out this shortcut. Until one of the men comes up to him and says, you know, hey, this is a great party, you're very, you know, love this repartee. He says, have you ever thought of taking up wrestling, competing in a wrestling competition? He goes, wrestling? I'm like an old man. Why would I do that? And he says, but look at how young your slaves are. The point is like, they can't do that

• 56:38Ryan Holiday?

  for you also. And, and I think we, we are under the impression, for instance, that like artificial intelligence is this magical transformative thing because it contains all this knowledge. But, but you still have to know what questions to ask it. You still have to be able to separate the good answers from the hallucinated nonsensical answers, right? It can tell you, you know, oh yeah, that quote you're talking about, it's in this book. But you have to know what that quote is, right? You have to know some, vaguely know what it is. And, and you can really only do that from the work. It can help you solve some problems, but if you

• 57:19Ryan Holiday?

  can't recognize a good solution from a bad solution, or bullshit from, from, from, from a real insight, it's not going to do much for you. And I, I think people think That people are always looking for some magical thing that will exempt them from having to do this really hard thing. And it almost never works.

• 57:40Chris Williamson?

  Do you know that story about chauffeur knowledge? Is this Richard Feynman, maybe, or somebody else's famous physicist in the 1900s? And he was going around giving the same lecture and over and over again. And his chauffeur was there at every single lecture that he gave.

• 57:55Ryan Holiday?

  Yeah.

• 57:55Chris Williamson?

  And after a while, the chauffeur basically knew the lecture off by heart. And he said, hey, wouldn't it be funny if one day we swapped? And you went up and I'll dress as the chauffeur and you'll come in. And this guy goes up and he gives the lecture and it's perfect. The exact same way that the guy that was supposed to do it. And somebody at the end asks a question and says, excuse me, I just need to ask you about this. He says, that is a question that's far too difficult for me. You're going to have to ask my chauffeur. And turns to the chauffeur that's the real guy.

• 58:20Ryan Holiday?

  Yeah, to know by heart is not to know.

• 58:22Chris Williamson?

  Well, Naval, Naval came on the show at the start of the year. And just this lovely idea, which is there is a big difference between appearing wise and being wise. And the temptation to rote memorize things that give the allure, the illusion of wisdom. Like this looks like being wise, because it is an insight that someone far smarter than me came up with.

• 58:44Ryan Holiday?

  Sure.

• 58:45Chris Williamson?

  The difference between being able to put that out, and that's not necessarily a bad thing. It's a right, okay. I, I understand and have retained the concept. That's a very good first start, because without understanding it and retaining it right down, right down, right down. You don't know it at all. So great first step. But what does it mean to be able to explain it three different ways? What does it mean to be able to apply it in your life? What does it mean to see that insight when you're gripped by emotion?

• 59:15Ryan Holiday?

  Yes. Yeah. To even recognize that there was a kernel of insight or truth in the idea is no, is not nothing. But then, yeah, to really know it is the next thing. And this is where the interplay between reading and study and exposing yourself to ideas. And then having experiences is so important. And it's also why it's a loop, because.

• 59:39Ryan Holiday?

  There are some things, you know, maybe narrative, nonfiction or whatever,

• 59:44Ryan Holiday?

  travel book or something, you read it once and you're like, I get, I get the argument. I get what I'm supposed to take from this. And then many of the great texts, literature, philosophy, plays, stories, poems, et cetera. You have to read, have experiences, read again, have experiences because

• 1:00:07Ryan Holiday?

  every vantage point that you look at it from, particularly with the passage of time, allows you to unlock something new in it.

• 1:00:16Chris Williamson?

  McConaughey says when he's reading a script, that he reads it when he's tired, when he's happy, when he's hungover. And each time that he reads it, because you don't have the luxury of taking five or 25 years to go back to fucking Crime and Punishment or whatever. You need a short period, okay, so how can I change my state? So that that different perspective that I'm coming in from, that different vantage point, I get access to.

• 1:00:39Ryan Holiday?

  Yeah, that, that makes a lot of sense. There are books that you, there are books, you know, people go, oh, I read that. And there are books that are designed for you to be reading. It's not a thing you have done, it is a thing you are doing. And this was easier to do in the ancient world because there were just fewer texts. You know, there was fewer, you know, you, you might read the Odyssey 500 times in the course of your life or hear Exposed because there's not any other, you know, major works to draw on. We have this, you know, we have all of human history. We have thousands of years of extra history and knowledge and art and stories that, that some of the ancients didn't have.

• 1:01:24Ryan Holiday?

  That's our, our blessing and our curse.

• 1:01:27Chris Williamson?

  Well, I think that's a, a really interesting challenge that we're facing.

• 1:01:32Chris Williamson?

  A lot of the time, people may have thought they knew who they were and in the modern world have sort of lost themselves. I had geographically triangulated who I am and why I'm here at this point. And then they go through a period of protracted challenge. They lose a thing, a person, a belief in themselves. And now this sort of paradox of choice, lots of options open in front of me, plus this unmooring from who they thought they were before, arrives them at a port that they have no idea where the ship sailed to. So what do you think a wise stoic would say about somebody who's lost themselves in life?

• 1:02:19Ryan Holiday?

  Yeah, it's when you, when you lose everything, there's something very freeing about that. When all your assumptions have been challenged or turned over, and there's something profoundly destabilizing about it because you don't, you don't have anything. So I think you go.

• 1:02:37Ryan Holiday?

  Maybe one of the things you do is you go back to those things that were formative to you at one point. And I've been thinking a lot now about like what I'm rereading, what I'm rewatching, what I'm reexamining. Because now that I am different, now that I am in different places, what I, what I, what strikes me about them is so different. But there is something nostalgic and beautiful about going back to something where you're like, well, I knew who I was when I read a Great Gatsby for the first time, because I was 17, and I know exactly what class I was in and what I thought was important. And I can, I can look here and see what I marked. Like Joan Didion has this famous essay

• 1:03:22Ryan Holiday?

  about journaling. And she says, you know, why did I record a thought that I had at a train station in Pennsylvania? Why did I write down this thing that I overheard someone say in a restaurant? Why did I write down this or that? Why did I tell this story? And she'd been journaling since she was five years old. Her mother gave her, she told her, she told her mother she was bored one day. And Joan Didion's mother said, well, here's a notebook. Why don't you write a story and then you can have something to read? And so she'd been taking notes for, for her whole life. And in this famous essay on notebook, she says, well, why did I, why, why do I do this? Is it a professional like rolodex? Is this like? Someday I'll find a story to put this quote in. And then she said, no, that's, that's, it's gotta be more than that.

• 1:04:06Ryan Holiday?

  She says, um, the purpose of journaling is to keep on nodding terms with who I used to be. She's like, that's what it is. It's to remember to who it's, it's to remember who I used to be. And there's something very powerful about journaling. Like I have this journal that I do every day where it has five lines on it. And, you know, so every five years I do a new one, but you write like where you were on that day, what you're doing, what you're thinking about five years ago or that, that day. And then you do it the next year and the next year and the next year. And the first year is kind of cool and the second year is kind of cool. But by three, four and five, it's very powerful because you're like, oh, you know, in September of 2022, this is what I was thinking about.

• 1:04:48Ryan Holiday?

  And that feels very urgent and important, or that feels like silly and weird. And, and so her, her point was that, that what journaling allows us to do is not just write down and record something, but it's almost like, um, it's like taking a picture on your phone and both cameras are working. Like it's taking the picture of what you're looking at and it's taking the picture of you as you're looking at it. And it, it depends on which of those is actually the more important image to capture. Right? And I, what I think journaling as a practice is very helpful to prevent some of those dark nights of the soul. I don't know who I am. I don't know what any of this means. I don't know what happened because you do know what happened.

• 1:05:32Ryan Holiday?

  You've been monitoring it and tracking it incrementally as you go.

• 1:05:38Chris Williamson?

  I wonder whether the meta lesson as well is nothing as, is as important as you think it is, apart from when you're thinking about it.

• 1:05:46Ryan Holiday?

  Yes.

• 1:05:47Chris Williamson?

  Like that moment when you are caught up in the rumination cycle, the worry, the despair. The depression, the anxiety, the concern. And, and although people unfortunately don't tend to journal when this is happening, the elation, the bravado, the overconfidence.

• 1:06:03Ryan Holiday?

  Yeah, the ephemerality of all of it. Like, uh, this is from Buddha, but, but this, the story is, you know, uh, the wisest philosopher in the world was asked to find a phrase that's true in any and every situation and always has been and always will be true. And what the answer that comes back is, and this too shall pass. And, and, you know, that can be, uh, true of grief. That can be true of, you know, an incredible triumph. It can be true of despair. It can be true of happiness, torture. All of it lasts, uh, long, less long than you think it does. And eventually it all does end.

• 1:06:45Ryan Holiday?

  Like it ends one way or another, the Stoics say, like, like you're, uh, the Stoics say, like, when you're feeling like profound pain or like sickness or whatever, you can say confidently to yourself, um, this is going to end. Either because it's going to kill you or it's going to go away. Right? And, and, um, sometimes it's only zooming out and getting a little perspective on your own life that you realize this is true. And then zooming out and looking at things historically that you realize, oh, this has always been true for every person who has ever lived.

• 1:07:17Chris Williamson?

  I was reading Unbroken about Zamparini. And I'd never read that. So, uh, my favorite stories are kind of solo or group people against the odds. Endurance by Alfred Lancing, uh, Forgotten Highlander by Alistair Urquhart.

• 1:07:34Ryan Holiday?

  Yeah, yeah.

• 1:07:34Chris Williamson?

  That I got you onto. Uh, and, uh, Unbroken, Laura Hillbrand, uh, about Louis Zamparini. And, uh, I said this to you last time, no one's done a good Stockdale book yet, have they?

• 1:07:46Ryan Holiday?

  I'm in the works.

• 1:07:47Chris Williamson?

  No way.

• 1:07:48Ryan Holiday?

  Mm-hmm.

• 1:07:48Chris Williamson?

  Let's fucking go, dude.

• 1:07:50Ryan Holiday?

  I'm, uh, I'm maybe three chapters in. I've, I've been.

• 1:07:54Chris Williamson?

  That's gonna be the next one?

• 1:07:55Ryan Holiday?

  That's, uh, the wisdom is this, and then that's, that's the next one. I, I.

• 1:08:00Chris Williamson?

  So perfect.

• 1:08:01Ryan Holiday?

  His story is fucking incredible, like so much better than you would think it is. Like, I think people think. Do we nerd out about Stockdale? Yeah, yeah, yeah. So for people who don't know, Stockdale was shot down over North Vietnam. He spends basically seven years in what's called the Hanoi Hilton, where he's tortured, spends the vast majority of that time in solitary confinement. Horrendously tortured. Okay, so the key to understand, like, it's not, it's actually a much more powerful story than even Unbroken, because Zamparini, I think I'm saying that right, is your ordinary prisoner of war, right? He is an enemy combatant held against his will, right?

• 1:08:46Ryan Holiday?

  So Stockdale is in effectively a re-education prison, right? Like, the job is to take these people, to break them and to turn them into propaganda assets. But the thing you need to know about Stockdale is Stockdale is in the air the night of the Gulf of Tonkin incident. So Stockdale is there at the beginning of the Vietnam War, which is begun under effectively false pretenses. So when he is shot down several months later, and he's parachuting into this camp, and he says to himself, you know, I'm entering the world of Epictetus. He's not just gonna be held captive and not seeing his family for, you know, however long.

• 1:09:29Ryan Holiday?

  He possesses the most terrible secret that you could possibly possess, other than perhaps knowing the nuclear codes or the, you know, like, there isn't a secret that his captors would have been more motivated to know than to know that he was in the air and watched them effectively, he says, "we were shooting at ghosts," that there was nothing there, that... Because the North Vietnamese know that they cannot win militarily. They have to win in the court of global public opinion. So imagine they were to come in possession of a pilot who was there, who saw his country do something wrong.

• 1:10:14Ryan Holiday?

  And imagine they could flip this person. So breaking isn't like, oh, hey, let me tell you like how a US aircraft carrier works, or let me tell you like the secret vulnerable spots on the F-16. He possesses the most significant secret of and...

• 1:10:32Ryan Holiday?

  Uh, you know, piece of information. So like

• 1:10:34Chris Williamson?

  he has a very special sort of artillery shell hidden inside of his brain.

• 1:10:38Ryan Holiday?

  Yeah.

• 1:10:38Chris Williamson?

  And that can be deployed by people who would really like that specific weapon.

• 1:10:42Ryan Holiday?

  Or just imagine the moral weight of what he is dealing with. So he's not, it's not like he is, um, you know, flying over Nazi Germany and he gets shot down and he's being held by the worst people of all time.

• 1:10:56Chris Williamson?

  He's the bad guys.

• 1:10:57Ryan Holiday?

  He is, he is, he is not, uh, fighting.

• 1:11:03Ryan Holiday?

  It's a, it's, it's, it's a morally complicated war.

• 1:11:05Chris Williamson?

  Doesn't have, he doesn't have pure virtue to stand on top of.

• 1:11:08Ryan Holiday?

  Yes. And he, and so he has to bear the weight of this.

• 1:11:11Chris Williamson?

  It's a flimsy position to.

• 1:11:12Ryan Holiday?

  Yes. And so what is he, what is he holding on to? He's holding on to this idea that he is his brother's keeper. And that if he betrays his country, who he's really betraying is the other 200 or so prisoners. And then all the other draftees and officers, he's betraying, he's, he's not worried about protecting Lyndon Johnson. Right. He's worried about the person in the cell next to him. And so the, the, the, the mental gymnastics and the moral injury and weight that this guy has is unfathomable. If you think about what he's dealing with.

• 1:11:52Chris Williamson?

  When you look at Alistair Ercard from the Forgotten Highlander, disentree for four years straight. Forced march, bridge over the River Kwai, et cetera, et cetera. Locked in a tin box, knocked off his feet by the bomb blast from Nagasaki.

• 1:12:05Ryan Holiday?

  Yeah.

• 1:12:05Chris Williamson?

  Hardcore shit.

• 1:12:06Ryan Holiday?

  That's like the equivalent of just climbing Mount Everest, which is just you versus the elements, you versus the situation.

• 1:12:12Chris Williamson?

  Attraction that's on this sort of one plane of existence.

• 1:12:16Ryan Holiday?

  Yes.

• 1:12:16Chris Williamson?

  What you're saying that Stockdale had was this like astral.

• 1:12:20Ryan Holiday?

  Yes.

• 1:12:20Chris Williamson?

  Karmic challenge that he's also fighting with.

• 1:12:23Ryan Holiday?

  Yeah. And, and yeah, so far I've been fascinated by his childhood. And then when he's at the Naval Academy, and this is what I've been learning out about. So when he's at the Naval Academy. When he's a senior, the first, the man, his name is Wes Brown, who would go on to be the first black graduate of the Naval Academy is also there. So he's the Jackie Robinson, effectively, of the Navy. And so, as Stockdale is this young student who's just trying to get ahead, he's watching this other guy go through this horrendous ordeal. Like, he had to have, like, basically guards on him because they were worried other midshipmen might kill him.

• 1:13:04Ryan Holiday?

  And there was a sustained campaign to give this guy, Wes Brown, demerit, so he'd get kicked out of the academy, so they wouldn't have to graduate him, and then he wouldn't become a naval officer. There'd only been, like, ten naval officers in history, black officers in history, before this happened. So he's watching another person go through, effectively, what he has to go through 20 years later, a sustained campaign to break you as a person and crush your soul, right? That's what the captors in the prison are not just trying to go, "Hey, if we don't give them food and water, will they turn on their country?" They're trying to break them as human beings.

• 1:13:48Ryan Holiday?

  You know, they're torturing them, they're playing mind games. And his famous thing, Stockdale, is tortured for days on end, and then they basically, in a moment, they switch. And they go, "Okay, it's too much. We pushed you too far. We're sorry. Why don't you go to the bathroom, clean yourself up? You can go back to your cell." And he realizes that they would never give him anything for free. They would never be nice to him for any reason. So he realizes, "Oh, there must be a reason they want to clean me up." And he realizes they're about to parade him in front of the cameras. They want him to give a videotaped statement. Maybe he's even sensing in this moment that they know what he knows. And so, at this moment, he walks into the bathroom.

• 1:14:32Ryan Holiday?

  He says he knew he had about a minute in there. And he begins to beat his face to a bloody pulp with the stool. And then he cuts, he shatters the mirror, and he basically scalps himself. Like, he cuts, he gives himself what he calls a reverse mohawk. He just takes this jagged edge and he cuts it off the back of his head. He basically makes himself...

• 1:14:55Chris Williamson?

  Unspeakable.

• 1:14:55Ryan Holiday?

  Un, un, yeah, he's bleeding everywhere and, and it's like they come in, they think he's trying to kill himself, but he hasn't. He's just, just maimed himself. So he is unfilmable.

• 1:15:06Chris Williamson?

  Not press worthy.

• 1:15:07Ryan Holiday?

  Yeah. And, and they go, you know, you know, what are we supposed to do? We were supposed to take you downtown and, and he goes, you tell the major that the commander won't be going downtown. And, and so he has this, you know, sort of this, like, this determination and this grit and this intensity that takes on a whole different color when you realize what he's holding and what he's been through. And that, that he realizes that, yeah, it's, it's about his connection to these people, which I think is interesting. What I'm, you find these threads, you go, oh, this is something that you believe at 38, however, he's in his late 30s when he's in this camp, now he's a commander, that he fundamentally didn't

• 1:15:51Ryan Holiday?

  believe when he was 20 at the Naval Academy. He doesn't participate in the hazing of this, of this guy, Wes Brown, but like famously Jimmy Carter, who's like from the deep south is in their class and Jimmy Carter runs across country with them. And Jimmy Carter is famously like this supporter, a guy who grows up in like the segregated South is there helping and encouraging this guy. And Stockdale's like sort of too busy doing his own thing. And so I'm, I'm fascinated. And how does this person go from like selfish in the way that when we're young, we're all, I'm into me and my thing and what I'm trying to do.

• 1:16:29Chris Williamson?

  I love me. Who do you love?

• 1:16:30Ryan Holiday?

  I don't have time for this other stuff, you know, like the, if not, if I am not for me, who is? And then he becomes by the end, if I am only for me, who am I? And that's the arc of Stockdale.

• 1:16:42Chris Williamson?

  Right. I cannot wait for you to do that.

• 1:16:45Ryan Holiday?

  I'm loving it.

• 1:16:46Chris Williamson?

  That's it. That's sick. And I guess. Conspiracy, tracking a story, but it's over like a tighter timeline, right? But a lot of investigation, what's going on, but this is like archive shit.

• 1:16:57Ryan Holiday?

  Well, yeah, to go to what we started with, like, uh, the reason I'm doing the book is because I've never done a book like this. And I wanted, I love those kinds of books. And so like, the book could come out and sell zero copies. The book could come out and everyone could say that I, I suck and I failed at it. But I have learned a lot, like I have, I have gotten better at what I actually do in struggling to do this thing, which is not what I normally do.

• 1:17:24Chris Williamson?

  Actually, I want to bring up a video of yours that I remember seeing. I want to say, did you video yourself getting the call from your publisher about the New York Times list of the last book or the one before?

• 1:17:38Ryan Holiday?

  I think I've done it a couple of times.

• 1:17:40Chris Williamson?

  Okay.

• 1:17:40Ryan Holiday?

  I know when the call's coming in.

• 1:17:42Chris Williamson?

  Okay.

• 1:17:42Ryan Holiday?

  So I flip on the camera.

• 1:17:43Chris Williamson?

  Yeah, there's, there's this video, maybe, maybe your kid's in the room or maybe not. Anyway, and you're, you're there and you're talking to them and they say, Ryan, just congratulations, bestseller, you came in at number, whatever the fuck. And, uh, you say, thank you very much. That's good. And then basically, but now I must get back to writing the next book.

• 1:18:02Ryan Holiday?

  Yes.

• 1:18:02Chris Williamson?

  And I remember, I remember watching that and you know, we've met, this is episode like seven. First time you come on the show was like fucking six, seven years ago.

• 1:18:08Ryan Holiday?

  Really?

• 1:18:09Chris Williamson?

  Yeah, yeah, forever ago, like when I was still in.

• 1:18:10Ryan Holiday?

  Oh, this is sick. I thought you were saying I was on sick. Got it. I get what you're saying.

• 1:18:14Chris Williamson?

  So I've got like a, you know, a good understanding of sort of, I think where you're at. I, I want you to ask you about that because

• 1:18:21Chris Williamson?

  that, at least from the outside, looks a little bit like somebody who is struggling to take a moment to celebrate their accomplishments because not, and I wouldn't, I wouldn't say that it's as, uh,

• 1:18:40Chris Williamson?

  Philosophically shallow as I'm just moving on to the next thing.

• 1:18:44Ryan Holiday?

  Yeah.

• 1:18:44Chris Williamson?

  I don't think it's that, but I do wonder whether there is a Puritan work ethic driving you to the point where this thing that happened, it's great, that by all accounts, I probably should put the fucking buck down, get some cake and allow my like, put the, put a couple of banners up. I know they're shit, like light some candles and, and have a little thing, have a little celebration. Is that, because I'm, I'm very interested. One of the criticisms typically of Stoicism is sort of a, a, a lack of celebration of the good, this sort of indifference to emotion that is good in times of strife, but kind of like having sex with a condom on in times of, you know, times of good. It's like a prophylactic

• 1:19:29Chris Williamson?

  against everything, unfortunately, including the celebrations. Um, did you consider taking the condom off at some point?

• 1:19:36Ryan Holiday?

  I, there's a couple of things there. I think talking about wisdom, one of the things you'll sometimes you can hear from older people is like, take the fucking compliment. You know, like, like some, you're, you're being like, oh no, it was nothing or I don't care. And they're like, no, no, I appreciated it. You should take the compliment. And that, I think that's something that, that everyone should work on. If someone's saying they like something, if someone's saying good job, be gracious with it because you think you're being self-effacing, but actually you're rejecting.

• 1:20:03Chris Williamson?

  It's a middle finger to them.

• 1:20:03Ryan Holiday?

  Yes, exactly. And, and I, I, I think that's something I've, I've tried to work on. Some people see that, they go, okay, like, so you, you hit number one, which I've been lucky enough to do a couple of times. And, and then you're just right back to work. Where's the joy? Where's the fun? Um, and my answer i- is that the joy and the fun is not in throwing a party for hitting number one. I like doing it. Like I, like, I like writing books. Like where I am right now in the book that I am writing is my absolute favorite place to be. Like I, I, I'm not in the early phases of like, what is this? Is this anything? I'm in the, the, the thick of like every day, there's like a challenging,

• 1:20:45Ryan Holiday?

  uh, invigorating, uh, problem to solve. And then I'm making progress on it and it's coming together. And I'm learning and I'm growing and I'm doing what I like meant to do. So one of the hardest parts of the schedule that I am on is that usually my my last project is coming out when I'm in the my favorite part of the next one.

• 1:21:08Chris Williamson?

  Right now, which is why you're so fired up about Stockdale when we should be talking about fucking wisdom.

• 1:21:11Ryan Holiday?

  Yeah, like I didn't really do I maybe got like 45 minutes of writing done today because I had a doctor's appointment and then I'm here and then I got to pick up. So like I'm actually not doing the thing that I like to do. Not that I don't like this, this is amazing, but like I like doing the thing that's and and I. I think early in my career, like all people, I I I was somewhat extrinsically motivated. Like I wanted to hit the best seller, best seller list. I wanted you to say it was amazing. I wanted recognition. I wanted all that and I I still do like those things and I'm not shrugging them off as nothing. It's just.

• 1:21:50Ryan Holiday?

  I just feel like the reward for succeeding should not be taking away from them. Like I'll tell you like my first, the first time I hit the New York Times bestseller list. Stillness is a key, stillness is a key debuted at number one in 2019. And I remember I woke up, I was in LA on book tour and.

• 1:22:11Ryan Holiday?

  I could, I mean, my alarm goes off my phone and one of my rules, I don't check my phone. The first thing that I do when I wake up is I I try to.

• 1:22:17Chris Williamson?

  But that's difficult on the road, right? Because.

• 1:22:19Ryan Holiday?

  Yeah, exactly.

• 1:22:20Chris Williamson?

  You're using your phone as the alarm.

• 1:22:22Ryan Holiday?

  And so so it's like, you know, you pick up your phone and you're like, some stuff has happened, you know? I can tell some stuff has happened and and I remember going. So staying at the Los Angeles Athletic Club, which is one of my favorite places to swim. And I go, OK, like, this is either good news or it's bad news about the book because it's coming from New York, right? So I'm on the West Coast.

• 1:22:42Chris Williamson?

  You're three hours behind.

• 1:22:42Ryan Holiday?

  Yeah, so I I woke up and I was like, I'm gonna go for a swim. I'm gonna swim my exercise. I'm gonna do the thing I love to do here. And the news is the news. It's like, you know, the cat in the box, right? It's like I'm either a bestseller or I'm I'm not. I should get to enjoy the swim either way. And so I went, I had this great swim. And then I checked in and I, I, you know, was a call from my agent and my publisher and my wife and it was great. But like, even if it had.

• 1:23:11Chris Williamson?

  Where the fuck have you been?

• 1:23:13Ryan Holiday?

  I was, I, I was swimming, uh, front stroke. In, in a way, the good news is just as much a catastrophe as the bad news. Right? Like the, the, the good news, if, if I get the good news and then I go swimming, I'm just thinking about that the whole time. Like pre- presence is the gift, just being in the moment, enjoying the thing is what you like.

• 1:23:34Chris Williamson?

  I am going to interject there. I abhor open loops.

• 1:23:39Ryan Holiday?

  Okay.

• 1:23:40Chris Williamson?

  Fucking, I am allergic.

• 1:23:42Ryan Holiday?

  You couldn't leave that on.

• 1:23:43Chris Williamson?

  I am allergic. Well, I'm working on it.

• 1:23:46Ryan Holiday?

  And that's the skill.

• 1:23:47Chris Williamson?

  I know that it's a, I know that it's a, a, a challenge of mine that not knowing what's going on with this thing. To me is the sort of shit that keeps me awake, the sort of shit that wakes me up at four in the morning. It's the sort of thing that causes me to be thinking about that when I should be thinking about whatever else.

• 1:24:07Chris Williamson?

  I would struggle with that. And yet, I would say as well, I've seen other videos, like random shit that just pops up from you. That there was this video where you're complaining about trash. Someone had left loads of trash like near the driveway to your ranch or something. There was another one about fence posts that might've even been like five years ago. And I do remember seeing some of these different way markers. And it's not representative, it's what you've recorded and chosen to put online that the algorithm's chosen to give to me that I can remember. There's a lot of film in here, but I do get a sense of, of like regulation.

• 1:24:40Ryan Holiday?

  Yeah.

• 1:24:40Chris Williamson?

  From, from seeing, from seeing your stuff. And there is something, uh, sort of wonderful in the purity and the, almost complementarily, the boneheadedness, the stubbornness, some might say, right? The, the, the, yeah.

• 1:24:55Chris Williamson?

  Single mindedness of some of these approaches that sure, some days I'm only going to get forty five minutes in, but for the most part, like this is, I am a writer, I am a thinker, I am a musician, and this is the main thing. And the main thing is for me to keep that the main thing. And I do find that, you know, as a supporter from the sidelines of that stuff, it is good to see somebody who I think, at least from the outside, appears to be trying to find that balance between I want to enjoy my life, I want to care for my family, I don't want to sacrifice everything in pursuit of the goal. But given that I don't want to sacrifice everything, and I want to make a dent in the world, I have to constrain the

• 1:25:39Chris Williamson?

  aperture of shit that I do down to a really, really, really small number of things.

• 1:25:43Ryan Holiday?

  That's interesting. Yeah, there's a lot there. I would say, regulation is the key to life, right? Getting emotionally regulated. That's what stoicism is. People think stoicism is the eradication of emotions. It is the regulation of emotions. It's not having none. It's, I'm feeling anger, I'm feeling frustration, I'm feeling envy, I am feeling worry, I'm feeling anxiety, and I don't have to impulsively act on that information, right? And so, how do you find, how do you build the practice of like, this is what I'm feeling, but this is what I'm gonna do, right? Exercise, a physical practice is a great metaphor, a training ground for this, because you're able to go like, I am feeling tired, I am

• 1:26:24Ryan Holiday?

  feeling not into it, I am feeling cold, I am feeling whatever, and you're saying to yourself, but that doesn't fucking matter, here's what you're gonna do, right? And so, how do you practice deciding who's in charge? That's, I think, really important. And it's something I think I've gotten better at over time, and you work on throughout your life. I think, I know that what I control is, and what I enjoy, is the doing of the thing. And I try to think less about the things that are not related to the doing of the thing. And so,

• 1:27:03Ryan Holiday?

  Writing is what I like, it's what I enjoy, it's what I'm best at. That's what I want to be doing. And then publishing is the stuff that comes out the other side. It's the, it's the byproduct of the discipline and whatever. And so that's, that's kind of how I think about it. Your point about these open loops, that I, I think that's a capacity you like, again, just it's, it's, it's a capacity you develop and increase. Like, hey, I'm deciding I'm not going to think about this until tomorrow. Or I am going to be here for this school performance. I'm gonna, uh, I'm gonna sit here for this, you know, however long this plane is delayed. I'm gonna, I, they told me I'm not gonna get an answer back on this medical test for two weeks.

• 1:27:46Ryan Holiday?

  I'm not going to waste two weeks.

• 1:27:49Chris Williamson?

  Speed.

• 1:27:50Ryan Holiday?

  Feeling shitty.

• 1:27:50Chris Williamson?

  Yeah.

• 1:27:51Ryan Holiday?

  And so how, how do you, how do you go, I decide what I'm going to think about. And to me, that's a very stoic practice, like, and I think you, you, you do it in the, in, you, you develop it intentionally over often insignificant things. So that in the significant things you could, you can do it.

• 1:28:08Chris Williamson?

  That's a good point. I mean, the,

• 1:28:12Chris Williamson?

  the ability to learn how to get out of quicksand is probably something that both of us could work out in an afternoon.

• 1:28:18Ryan Holiday?

  Yeah.

• 1:28:18Chris Williamson?

  And we could practice it. If you're trying to learn that while you're in quicksand. That's going to be significantly more difficult.

• 1:28:24Ryan Holiday?

  Also, quicksand doesn't exist.

• 1:28:26Chris Williamson?

  But is it not?

• 1:28:27Ryan Holiday?

  It's basically a trope from westerns in the 50s.

• 1:28:30Chris Williamson?

  I've been psyoped by fucking American TV.

• 1:28:33Ryan Holiday?

  Well, I mean, it, it's one of those things where like, I gotta be aware of quicksand. It's like, have you ever experienced, you've been all over the world. Have you ever seen quicksand?

• 1:28:39Chris Williamson?

  I haven't seen quicksand, but I, you know, I wasn't in America in the 50s. So maybe that's a, I, I, but yes, exactly. Do you think intelligence then is overrated when compared with equanimity?

• 1:28:51Ryan Holiday?

  Well, I think intelligence poised with equanimity is a very powerful thing. And there's a lot of intelligent people who don't have it. And it prevents them from being as smart as they can be. You know, Marcus Aurelius's stepfather, the emperor before him, Antoninus, his last, his, his final dying word is equanimatus or equanimity. That's what he's trying to pass to his, uh, to his son. It, it's like the most powerful thing that a leader, a parent, a human being can have, right? Is the ability to sort of. Be even to be regulated. Again, this is easy to do when the world is simple and things are calm and nice, but that's not how it is.

• 1:29:34Ryan Holiday?

  Right? So it's like, like when you have children, especially like they can't be regulated if you're not.

• 1:29:41Chris Williamson?

  Yep.

• 1:29:42Ryan Holiday?

  Well, well, you see this if you have a dog, right? You're like, the dog is crazy because you're crazy. The dog is responding to your energy. And what is it? It can, it can sometimes be helpful to have something as unbiased as.

• 1:29:54Chris Williamson?

  That's why people love equine therapy, right? Because you have this creature, which is really fucking sensitive. It, it gets a little woo. There's some stuff that I went to equine therapy.

• 1:30:04Ryan Holiday?

  Done it.

• 1:30:06Chris Williamson?

  The lady that was there that was really lovely was telling me about how the horse's heart has a magnetosphere and it's able. I'm like this, I'm, we're getting into some astral realm shit here, but I do not deny prey animal twitchy as fuck.

• 1:30:21Ryan Holiday?

  If you have bad energy, it'll hurt you.

• 1:30:22Chris Williamson?

  You're fucked.

• 1:30:23Ryan Holiday?

  You, you, you would go, oh, okay. And, and then you, yeah, some of these things can seem very woo woo. And then you go, hey, but I came into this, this way, and now it's acting this way. There's clearly been some kind of.

• 1:30:32Chris Williamson?

  Literally false, functionally true.

• 1:30:34Ryan Holiday?

  Yes, yes.

• 1:30:35Chris Williamson?

  Or maybe fucking literally true, functionally true.

• 1:30:37Ryan Holiday?

  Yes, and, and, yes, it, it, it exists. It doesn't, it obviously isn't real, but it's obviously real.

• 1:30:43Chris Williamson?

  Something's happening.

• 1:30:44Ryan Holiday?

  You know what's another good example of that is like a hot streak. Like statistically, obviously it makes no sense, but there is something about being in, in the zone. Right?

• 1:30:54Ryan Holiday?

  But yeah, you, you, you go, oh, okay. It's, it's about how well can you, how, how good are you at going from dysregulated to regulated? That's what Stoicism is.

• 1:31:04Chris Williamson?

  I think a wonderful game for couples to play is something like when we get out of connection, the game is how quickly can we get back into it?

• 1:31:15Ryan Holiday?

  Yes.

• 1:31:15Chris Williamson?

  And like, what a wonderful goal for you both, because it's the dopamine. It's this sort of cohesive, we're working together thing. It's a challenge. It's not you against each other. It's you against the problem.

• 1:31:26Ryan Holiday?

  Yeah, that's the third thing that is your relationship.

• 1:31:28Chris Williamson?

  Yes, yes, yes, yes. How quickly can we both get back into that? Well, I'm going to do the thing that I know brings you back in and you're going to do the thing. And I, that's something, it feels like some shit that Matthew Hussey's probably said. He probably has it some.

• 1:31:40Ryan Holiday?

  Have you had Dr. Becky on?

• 1:31:41Chris Williamson?

  Dr. Becky.

• 1:31:42Ryan Holiday?

  Dr. Becky Kennedy?

• 1:31:43Chris Williamson?

  No.

• 1:31:44Ryan Holiday?

  She's, I know you don't have kids, but it's the, she's like the parenting guru of our time. One of the, the fucking greatest. She's like, don't try to be a perfect parent. Try to get better at repair because you're gonna screw up. You're gonna get dysregulated.

• 1:31:57Chris Williamson?

  A rupture is gonna happen.

• 1:31:58Ryan Holiday?

  It's about how quickly you can come back and fix it and address it.

• 1:32:02Chris Williamson?

  Doctor Becky stole my idea.

• 1:32:03Ryan Holiday?

  And so it's about that.

• 1:32:05Chris Williamson?

  Talking about the intelligence equanimity thing. And I think, you know, a lot of very intelligent people struggle to be equanimous.

• 1:32:13Ryan Holiday?

  Yes.

• 1:32:13Chris Williamson?

  And I don't know whether a lot of equanimous people struggle to be intelligent. But I think that one of the things that people who have got sort of deep in a piece, at least in my experience, sometimes struggle with is that sort of outward drive to make a dent in the world.

• 1:32:27Ryan Holiday?

  Yes.

• 1:32:27Chris Williamson?

  And that's fine because like you are your own unit.

• 1:32:31Ryan Holiday?

  Yeah.

• 1:32:32Chris Williamson?

  And who the fuck is anyone to say you're peaceful and largely content? But have you not considered making yourself feel unworthy so that you can go and, you know, write bestselling books?

• 1:32:42Ryan Holiday?

  Yeah.

• 1:32:42Chris Williamson?

  Anyway, um, I guess another, like an interesting question with regards to the wisdom thing is, what are the mistakes that otherwise smart people make?

• 1:32:54Chris Williamson?

  Most often that stops them from becoming wise? Basically, what is the disadvantage that a person who is very clever has of achieving wisdom? Are there certain hurdles that they need to overcome?

• 1:33:08Ryan Holiday?

  Well, I think we could say that there's a number of things that really smart people do that make them stupid. Right? Ego is obviously one of the things that makes us very dumb. Right? Because it, it, it filters everything through the lens of what we want to be true or how we see ourselves, what our identity is and not how things actually are. So ego obviously makes us pretty stupid. Obviously, bad information makes, uh, uh, smart people stupid. And of course ego contributes to this. If you, if you, uh, you know, crafted information diet that's about confirming what you already think or what you want to be true because you're so fragile and it challenges your ego, you're obviously gonna get very stupid. I think we could say that, um, you know,

• 1:33:54Ryan Holiday?

  Again, they seem to all center around ego, but you know, stop becoming complacent, ceasing to learn. If you're a know it all, right? You've learned everything that it's possible for you to know, right?

• 1:34:05Chris Williamson?

  That line that you've got about you can't learn something you think you already know?

• 1:34:08Ryan Holiday?

  Yes, that's that's Epictetus. But I think another way we get very stupid is you see people acting stupidly out of a lack of empathy. Like Elon said, you know, empathy is going to be the death of Western civilization. Empathy is like the key to the greatest achievements of Western civilization and humanity, the ability to strategically understand what is going on over there. What do they think? So going back to Socrates, Socrates says, you know, no one is wrong on purpose, right? Going, oh, they've thought themselves into this position. They don't think they're being stupid. They think they're being right. You

• 1:34:47Ryan Holiday?

  know, Temple Grandin famously watches this video. She gets called in by these by these cattle ranchers who are trying to vaccinate their cows against these different illnesses. And they put them through this chute. The cows are freaking out. They didn't want to go in the chute. They weren't even being like killed or hurt. They just didn't want to go in the chute. And they're, you know, forcing them and forcing them and forcing them. And she with a black and white camera gets in and takes pictures and the black and white camera approximates how the cow is seeing the world. She realizes that a lot of these things are seem scary to a cat, like a hose on the ground looks like a snake in black and white.

• 1:35:25Chris Williamson?

  Right.

• 1:35:25Ryan Holiday?

  Or she goes, when you get down on the cattle chute, this this chain that's rattling against the gate, sounds incredibly loud. And then it makes one cow scared, which makes another cat. And then that energy is. So, so the ability to get down and think about why someone else is thinking about what is, there's this German word umwelt, which means like the worldview of someone else. What is it like to be a bat? What's it like? You know, what's it like to be my eight year old? Because it's not the same as how I can. So I'm going like, do this, you have to do this. But that's from my view of 30, you know, more decades on this planet than than him is to go, yeah, what is it actually? How are you thinking about this? What do you not understand? What have you not had time

• 1:36:08Ryan Holiday?

  to experience? So empathy to me is, is the key, not just to like being a good person. It's key to the virtue of justice. But like, when you look at most of the enormous blunders of history, you know, Iraq, Vietnam. Fundamentally, it's this sense of like, well, here's what we think should happen. Here's how we think it's gonna go. And then this, um, this inability to conceive of the other people in the equation as being rational or reasonable or even, uh, significant actors, right? Uh, engraved on the Temple of Apollo, where the Oracle of Delphi sat, it said, you know,

• 1:36:50Ryan Holiday?

  uh, one of the, one of the epigrams famously, uh, we know, one of the famous ones is know thyself. But the other one is offer a guarantee and disaster threatens. Right? So you think you know how it's gonna be. You think you know how it should be. This is often exactly what precedes like the biggest blunders of history. The lack of empathy to go, what do they think? What do they want? What are they gonna do if we do this, right? And so I think there's, there's a number of kind of blind spots or, um, uh, impediments to our intelligence or wisdom. And, and so really, um, being wise is the removal of some of those things.

• 1:37:34Ryan Holiday?

  Like Socrates, you know, someone is sent to that same oracle to ask why Socrates is so wise. Cause he doesn't think that he's wise. And it comes back, you know, he's the wisest man in Athens. And as Socrates thinks about it, he realizes it's because he doesn't think that he's the wisest person, that he is in fact wisdom. So it's like, what are the, if, if we go, hey, I wanna be wiser, I wanna be smarter. It's stepping back and going, well, where am I being stupid? Like, what are, what are the things that are making me stupid? That, that are impeding my judgment, impeding my ability to discern, to see what's really here? And how do I strip those away? That's how we get wiser.

• 1:38:12Chris Williamson?

  Do you know the idea from mathematics of never multiply by zero?

• 1:38:15Ryan Holiday?

  No.

• 1:38:16Chris Williamson?

  Okay, so, um, take as big of a number as you want. Uh, 2,343,000, times it by five, times by 52, times by 17 million, times by zero.

• 1:38:29Chris Williamson?

  You get zero. Yes. Right. So you never multiply by zero. And it's basically an argument that you can continue playing the game as long as you're not kicked out. It's the reason that using too much leverage when you're trading is a bad idea. Yeah. Going bankrupt is a bad idea. You can spend all of the time that you want looking after your health. You eat a grass fed diet, you avoid seed oils and red forty, but one day you decide to not wear your seatbelt in the car. Yes, sure. Zero. Yes. You spend your teenage years working very hard at your education. You make it to university, you're just about to start on this brand new adventure and you have unprotected sex and get somebody pregnant. Not quite zero. Yeah. But fucking big, big change. Avoid the, the major stupid things. Correct. Avoid the major stupid things.

• 1:39:10Chris Williamson?

  And that idea of, okay, in the world of business and in the world of sort of objective outward metrics of success, I probably should double down on my strengths because my highest point of contribution is where all the gains accrue to the very, very top. Right? Power law. So move yourself up. Oh, you're ninety nine point five. Get to ninety nine point six. That's really great. It's a huge, big change. However, when it comes to life, like the shortcomings are what's going to kill you. There's a, a great idea from Visakh and Varasamy and he says, he calls it the divorce paradox, which is, uh, why do people who are seemingly the best friends in public, uh, so reliably end up breaking the marriage apart?

• 1:39:51Chris Williamson?

  And it's because we don't realize that the bad times and the way you deal with bad times are a much better predictor of long-term marriage success than how much you enjoy the good ones. Nobody, I would, I would estimate most marriages don't end because of too few peak experiences. Sure. Many will. Yeah. From too many and too, uh, too much rupture without repair. Yeah. Effectively, like that is what pulls you down into negative equity within a relationship. And you can reinvest that back in, but really the, it's like calories, right? Why is it that you control your diet more than you control your expenditure when it comes to exercise? Because it's way easier to eat four hundred calories than it is to expend them.

• 1:40:33Chris Williamson?

  And I think marriage, as the non-married guy in the room, is, uh, similar to that. Yeah. That the amount of work you need to do in terms of good things to offset that fucking shit argument you just had last night is an awful lot. Yeah. So, hey, control your calories, like make sure you get good at, at repair after rupture in the same way as ensure that you don't multiply by zero.

• 1:40:56Ryan Holiday?

  In your personal life. I was just thinking of a couple more things that smart people do that make them stupid. One is like you don't deal with your childhood issues, right? So you you are very smart. You are very successful. You are very powerful, but there is a part of you that's an 11 year old. There's a part of you that's an angry teenager and that person is is not who you trust with these high stakes. Have you done much sort of emotional work? What's that look like? Yeah, the the inner child work, I think, is really key. When you find it, when you find that kind of very young, very impulsive, very impetuous, very sensitive part of yourself, that's usually something that you haven't dealt with. That's a kind of a state of arrested development inside you like that. You know, there's the there's the they say there's the adapted child, right?

• 1:41:40Ryan Holiday?

  The child that has to the the decisions, the assumptions you make about the world because your environment was not perfect growing up, right? Those are coping mechanisms that made sense when you were 13 and your parents were splitting apart. Or, you know, you were an attractive nerd who was bullied or, you know, you you you lost a bunch of people that you you make these. You were abused. You went through these things, so you made certain assumptions or adaptations to to survive that. And maybe that's not good now that you're the leader of a company of 1,000 people or that you're, you know, making films in Hollywood. You you can't afford to be that 13 year old, right?

• 1:42:20Ryan Holiday?

  So I I think you sometimes you see people, you know, like, is it the classic midlife crisis? Like, you're blowing up your life because there's some part of you that's like trying to get back to some earlier part of you, right? And so I think you can see people who have sort of very smart, very rational in most aspects of their life, but they're making sort of very impetuous, irresponsible decisions because they're they've left something unaddressed. The other the other thing I think we see people do that makes them stupid is like, and this goes to the idea of information diets. But I think I've as I've gotten older, I've just seen more and more smart people that I know just kind of lose it like lose like go crazy, right? Like, like, your your inputs are very important.

• 1:43:04Ryan Holiday?

  And also taking care of this vessel is important. And so, you know, I think sleep deprivation is cumulative. The drugs you take are cumulative.

• 1:43:15Chris Williamson?

  Yep.

• 1:43:15Ryan Holiday?

  The stress you put on yourself is cumulative. Your, the lonely nights is cumulative, right? The, the hours that you work is cumulative. And, you know, you, you get to a place where something snaps, right? John Stuart Mill is one of the smartest people who ever lived. He has this crazy education and he snaps at like 20 years old.

• 1:43:39Ryan Holiday?

  You know, you can only wind the rubber band so tight. And, and I think you see that. So people, people make really bad decisions. And it's, it's this, it's like this trauma that they're not addressing. And then it's producing new trauma in the present moment.

• 1:43:54Chris Williamson?

  There's something that sort of fall is, especially in someone who's really, really smart. It feels extra catastrophic, pitiful. There's this sense of, oh, wow, it happened to them. Therefore, how am I a mere mortal protected from this thing?

• 1:44:15Ryan Holiday?

  Well, they're actually more vulnerable to it than you are. Because imagine you've gotten really used to trusting your instincts. You've gotten really used to being right. You've gotten really used to making contrarian bets. Like a friend of mine said, you know, having a, making a contrarian bet that you turn out to be like massively right about can be a brain destroying experience.

• 1:44:36Chris Williamson?

  Oh, that's so great.

• 1:44:38Ryan Holiday?

  Because you've just learned that everyone else is an idiot and you're really smart. And that, that even though everyone is pointing out this problem and that problem, what about this? And what about this? You are, you are, you are learning the wrong lesson from that, which is like, not like, oh, this is the one in a thousand times. You're like, no, no, this is every time. And so often that's why people who build like transformative companies or artists who are, had its reputation for being transgressive. And, you know, they get themselves into trouble later because.

• 1:45:11Chris Williamson?

  They drink their own Kool-Aid.

• 1:45:12Ryan Holiday?

  They're just playing that same. Saying again, and it's different circles.

• 1:45:17Chris Williamson?

  I think we all have this sense that our view of the world is the right one, right? We're all biased toward that. And if there is a time where your view of the world seems to be contrary to most of all other people, and you get to stand atop this big pedestal.

• 1:45:38Ryan Holiday?

  Yeah.

• 1:45:38Chris Williamson?

  Say, fuck you all.

• 1:45:39Ryan Holiday?

  Yeah.

• 1:45:40Chris Williamson?

  I was right.

• 1:45:40Ryan Holiday?

  Yes.

• 1:45:42Chris Williamson?

  The allure to think, run it back. Like, we're doing it again.

• 1:45:46Ryan Holiday?

  Yes.

• 1:45:46Chris Williamson?

  Is so strong.

• 1:45:48Ryan Holiday?

  It's and and this goes to what we're talking about, though, is like, OK, so that's a historical fact, right? Like, there are so many great historical examples of that same thing happening. So you want to learn, you want to see that so you can recognize the pattern in your own life, which is almost certainly not going to be as catastrophic or as significant, right? So when I went to my publisher in 2011 and was or 2012, and I was like, hey, I'd like to write a, you know, about Stoic philosophy. They were like, what? You know, and and that was not a thing they were excited about. Now, I ended up being obviously very right about that. But I try to actively think about why they thought it was a bad idea and in what ways they were right.

• 1:46:29Ryan Holiday?

  And in what ways I was correct, but only accidentally so. You know what I mean? Like, I wasn't this far-seeing genius who predicted all of this was going to happen. I had an idea for one thing that I wanted to do.

• 1:46:44Chris Williamson?

  So question on that, how and I I put myself in the camp of someone who doesn't have the courage of his convictions as much as I think I should.

• 1:46:52Ryan Holiday?

  Hmm.

• 1:46:53Chris Williamson?

  I think not fantastic at listening to my instincts, not fantastic at listening to my gut, very sort of top-down, not bottom-up.

• 1:46:59Ryan Holiday?

  Yeah.

• 1:47:00Chris Williamson?

  Very sort of existing above the neck. For me, I get the sense that it would probably be a good thing for me to maybe go, I think I'm right on this. And I I'm going to commit to that. What is your, what, give me the the contrarian perspective on this.

• 1:47:18Ryan Holiday?

  What you want to do is go, OK, I'm having this feel like I'm I'm doing this and I'm getting this pushback, or people are questioning it for this reason, or it seems, you know, like a impossible task for this reason. And then is the part of me that's resisting that?

• 1:47:34Ryan Holiday?

  Ego, or is it like, no, I have secret knowledge here? Is it that I've really done the work? I've really thought about this and I have an answer for that. Right? I think about this when I get edits back on my book. I don't like getting edits, right? Is my objection to the idea of, am I feeling this as the 15 year old who doesn't like to be told what to do? Or, and some of those notes, that is what's happening. And I need to put, I need to talk to that kid and go, this person is trying to help you. You should listen to them. And then there's the part of me that, that knows what I'm trying to do and knows what I'm trying to say, and has really thought about this. And I have an answer to why that's not a correct bit of feedback.

• 1:48:13Ryan Holiday?

  And distinguishing between the impulsive emotional resistance and the sort of rational courage of your convictions is a different, is, these are very different things. And I think that's really important. And so it's probably better that you're not, you know,

• 1:48:30Chris Williamson?

  Blowing shit up on a whim.

• 1:48:31Ryan Holiday?

  Yeah, this sort of missionary, you know, profit thing of like, that's, that's what's good, that might serve you well until eventually it blows you up.

• 1:48:41Chris Williamson?

  Higher likelihood of multiplying by zero.

• 1:48:43Ryan Holiday?

  Yeah.

• 1:48:43Chris Williamson?

  By doing that.

• 1:48:44Ryan Holiday?

  And so, so I go, I try to think about, okay, I wanted to write these books about Stoicism, this book about Stoicism, and it turned out I was right. What are the good lessons to learn from that? And what are the lessons, the lies, that I want to make sure I'm not taking from that? And then, you know, like this bookstore that I opened, you know, like it was a stupid idea. It was crazy. It shouldn't have worked. It did work. Now, why did it work? It was because I, I thought about why it would work and I minimized the downside and I, I.

• 1:49:13Chris Williamson?

  Turned it into a fucking office.

• 1:49:14Ryan Holiday?

  Yeah.

• 1:49:14Chris Williamson?

  Right off this thing.

• 1:49:15Ryan Holiday?

  That's, that's not the lesson. The lesson is not, when I feel like doing something, I should just do it. And people, you know, are always trying to hold me back. And, and so those are just like a couple minor examples in my life that, that. I was able to learn and recognize in the moment because I watched, you know, because I've read about, you know, this Nobel Prize winner who thinks they found a magical cure for this. I mean, like Newton got into like alchemy. You watch how smart people learn the wrong lesson from their success. And then you want to make sure that when you experience success or you have these analogous moments in your life,

• 1:49:56Ryan Holiday?

  you're like, okay, this is my opportunity in a low stakes, low key way to learn the same lesson. As opposed to needing to escalate, escalate, escalate to eventually learn it catastrophically.

• 1:50:09Chris Williamson?

  I love that idea of sort of a dose response. Or there's a particular waterline that you need to get past in order to have this unteachable lesson. Well, some people are more and less teachable than others.

• 1:50:20Ryan Holiday?

  Yes.

• 1:50:21Chris Williamson?

  So I guess.

• 1:50:24Chris Williamson?

  We mentioned that what are some of the impediments of intelligence to wisdom? Another interesting question would be something like, what are the prices that a wise person pays that an unwise person doesn't? What are the costs of being wise?

• 1:50:39Ryan Holiday?

  Yeah, I mean, self consciousness, it can be tricky. Like there is a, if you've never done it before, you know, you don't know how hard it's going to be. You don't know what to be wary of, you don't know what to be intimidated by, you can just plow ahead, right? And I do think in art, creativity, business, self consciousness is sometimes an impediment. It's an, it, you're overthinking, right? And so wisdom, if wisdom paralyzes you, if wisdom makes you think about everything from every angle, and thus deprives you of the energy or the enthusiasm to do the thing, that can be a real problem. I think the other, the other

• 1:51:21Ryan Holiday?

  side effect of wisdom, although it's not really wisdom, but they can be associated with each other is like a sort of a certain cynicism. Right? Like, uh, Feynman talked about how like you shouldn't lose the wonder. Like, you know, he says, you look in through a microscope, he says, you know, does it make your heart flutter? It should still make your heart flutter. And there is something where the, the byproduct of the learning and the understanding and the experience, the years of it can make you kind of jaded and cynical and that. That's sad and tragic. And I think you you have to. It shouldn't deprive you of hope. It shouldn't deprive you of purpose. It shouldn't deprive you

• 1:52:04Ryan Holiday?

  of these really wonderful things. It just means you have to work for them in a new way.

• 1:52:08Chris Williamson?

  Mm hmm. Ryan Holiday, ladies and gentlemen, dude, you're great. I appreciate you. I can't wait for the Stockdale book.

• 1:52:17Chris Williamson?

  Where should people go? Keep up to date with the million things?

• 1:52:19Ryan Holiday?

  Uh, Deo Stoic, Deo Stoic on YouTube. I think my name on YouTube. I don't know. Just Google around. They'll figure it out.

• 1:52:26Chris Williamson?

  Fuck yeah. Ryan, I appreciate you.

• 1:52:27Ryan Holiday?

  Thanks, man.

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