Why Most Smart People Become Stupid - Ryan Holiday

Chris Williamson 0:00 How did the live shows go? The last time we were talking-

Ryan Holiday 0:02 Oh.

Chris Williamson 0:03 ... we were discussing your upcoming live shows.

Ryan Holiday 0:05 Yeah, I think it was, uh, I was doing two in Australia, and you gave me this advice. You were like... Well, y- you told me that you'd d- done it with no notes (laughs) . And, uh, 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 int- Like, it, I, it's good to pick arbitrary challenges and take something that you're good at, that you've done a lot of times, and just figure out a way to do it the hard way.

Chris Williamson 0:35 Yeah. What's new?

Ryan Holiday 0:36 Yeah. And so I had to sort of reinvent it from scratch, and it was challenging but good. It's, uh, it's actually funny. In Marcus Aurelius Meditations, he talks about practicing holding the reins with your non-dominant hand.

Chris Williamson 0:48 Mm-hmm. Mm-hmm.

Ryan Holiday 0:48 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?

Chris Williamson 0:58 Hmm.

Ryan Holiday 0:58 And to force yourself to do it in front of, uh, the way that you're not comfortable doing it in front of 2,000 people-

Chris Williamson 1:04 A huge fucking audience.

Ryan Holiday 1:05 ... is a, is a... You know, it's a whole thing.

Chris Williamson 1:07 Difficulty plus, yeah.

Ryan Holiday 1:08 Yeah.

Chris Williamson 1:09 I've always thought about doing a podcast episode with a guest that s- somebody had organized for me-

Ryan Holiday 1:15 Yes.

Chris Williamson 1:15 ... and sat down opposite me, and I didn't know who it was.

Ryan Holiday 1:18 Yes.

Chris Williamson 1:18 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-

Ryan Holiday 1:31 Yeah.

Chris Williamson 1:31 ... trainer, like you motherfucker and do it without, like, destroying the episode. I always thought that would be, like, a fun challenge.

Ryan Holiday 1:37 Well, and, and the reason you challenge yourself artificially is that, uh, life doesn't really care about your plans.

Chris Williamson 1:44 Doesn't play by your rules.

Ryan Holiday 1:45 So I, I had a talk I was supposed to do in Kentucky, like, a couple weeks ago, and so I was supposed to fly in. Uh, I had all day, and then I would do the talk at night. And then, you know, I get to the airport at 9:00, and it's like 30 minutes delayed, 30 minutes delayed, 30 min- It's starting to get crazy. And some incredibly complicated, very expensive travel adjustments later, (laughs) I land, and I'm in the car. Like, it's... I'm already late, so they've pushed it. They've s- they've been stalling.

Chris Williamson 2:12 Everyone's there.

Ryan Holiday 2:12 Everyone's there, and I'm the last speaker. And, uh, 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?" And I go, "What do you mean? Like, I n- I know for a fact they came in yesterday, um, so you should definitely have them, but, um," like, "Here they are again." And I'm like texting, "Here, here's the link to the, here's the Dropbox link to the slides again." And they're like, "Okay, awesome." And then, uh, so, you know, they (laughs) I get there.

Chris Williamson 2:46 Seven minutes to go.

Ryan Holiday 2:47 Yeah, seven... They, I open the door, uh, of 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 micing me up, they go, "And you don't have slides, right?"

Chris Williamson 2:59 (laughs)

Ryan Holiday 2:59 It's like, "Is no one talking to each other?"

Chris Williamson 3:01 (laughs)

Ryan Holiday 3:02 But, like, like, now I know for a fact that you've had the slides for at least seven minutes, you know. (laughs) Uh-

Chris Williamson 3:08 (laughs)

Ryan Holiday 3:09 ... so, so, uh, and, and there's, like, a band on stage performing, uh, uh, that's stalling 'cause it's like a... So-

Chris Williamson 3:16 Hold up, hold up.

Ryan Holiday 3:16 It's an unusual-

Chris Williamson 3:18 Okay, yeah. Leap of the song.

Ryan Holiday 3:18 And then 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, w- you know, we had a live band performing, uh, a, like a (laughs) song that I like, but no slides. And then he's, uh... 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-

Chris Williamson 3:45 Resettle.

Ryan Holiday 3:46 ... and then bu- I walk in, so I start to talk a- and I'm, you know... Now I've got, you know, 45 minutes of time to fill with no slides, and you can't just do the talk you were gonna give without slides because it's, it's a hol- You can't be like, "Normally there'd be a slide." (laughs) You-

Chris Williamson 4:01 Every other minute.

Ryan Holiday 4:02 Yeah, exactly. And so I'm like, uh, "What am I going to 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-

Chris Williamson 4:12 Oh, the com-

Ryan Holiday 4:12 "Slides are-"

Chris Williamson 4:12 ... the comfort monitor.

Ryan Holiday 4:13 Yeah. (laughs) He's like, "Slides, slides incoming. Should be about 10 minutes," you know, and it's like, "This, this is too late, man." Um, but, but, uh, you know, I was able to just give some version of the talk that I've now given several times-

Chris Williamson 4:25 Mm-hmm. But new.

Ryan Holiday 4:26 ... to a live audience.

Chris Williamson 4:27 Maybe some new shit came up.

Ryan Holiday 4:28 Yeah, of course, but, but, but the interesting thing is, like, you think y- It, uh... 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 are 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.

Chris Williamson 4:54 Mm-hmm.

Ryan Holiday 4:54 So, you know, but, like, you... Technical difficulties are a part of any industry and life, and so if you, if you, if you ex- if you need it to go a certain way, you're very vulnerable. If you're good with it going effectively any way-

Chris Williamson 5:10 Mm-hmm.

Ryan Holiday 5:11 ... then you'll be all right.

Chris Williamson 5:13 Yeah. What happened with that Naval Academy-

Ryan Holiday 5:18 Oh, my God. (laughs)

Chris Williamson 5:19 ... speech?

Ryan Holiday 5:19 There was a... That was slightly different technical difficulties. So, you know, normally you send your sl- Like, so for the last four years, I've been speaking every year to the incoming class of the Naval Academy. It's called Plebe Summer. Um, so these are, like, the brightest kids in the country, future naval officers, so they're gonna run submarines and fly F-16s and command aircraft carriers. I mean, uh, future presidents, future admirals, future heads of the CIA.

Chris Williamson 5:46 Real-world Top Gun shit.

Ryan Holiday 5:47 The- These are the, these are the best, you know, most promising people in the world, actually, 'cause the Naval Academy sometimes has, like, students from other countries on these sort of guest programs. So, uh, e- every season, uh, every year for the last four years, I've been doing this series of lectures on the cardinal virtues, courage, discipline, justice, wisdom. So I've done courage, done discipline, I've done justice, and then I was supposed to do wisdom this year. And, um-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-

Chris Williamson 6:18 Mm-hmm.

Ryan Holiday 6:19 ... because, you know, they don't have the plug or... You send them in advance. Uh, so I sent them in, you know, the night before, um, as I had for every 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 gonna talk about. Um, 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. Um, as part of this order from the president that was supposedly about addressing, you know, DEI and wokeness or whatever, they had removed books that talked about those themes from the library.

Chris Williamson 7:18 Okay.

Ryan Holiday 7:18 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.

Chris Williamson 7:30 Mm-hmm.

Ryan Holiday 7:30 But you can't remove books from an elite university 'cause you don't like what's in the books. That's a very different thing.

Chris Williamson 7:37 Well, uh, there's an interesting point there. Was it, uh, Megan Phelps-Roper that did The Witch Trials of J.K. Rowling?

Ryan Holiday 7:43 Mm-hmm.

Chris Williamson 7:43 So this was the inverse of that situation, that was, uh, one book, or one series of books, Harry Potter-

Ryan Holiday 7:50 Yeah.

Chris Williamson 7:50 ... uh, originally in the '90s and 2000s by right wing-

Ryan Holiday 7:55 Yeah.

Chris Williamson 7:55 ... fundamentalist Christians. They campaigned to have them banned from schools because they were worried that it was rich- witchcraft.

Ryan Holiday 8:01 Yeah.

Chris Williamson 8:01 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 round, this is right wing-

Ryan Holiday 8:12 Right wing ca- Yeah.

Chris Williamson 8:12 ... in the modern world, trying to get rid of books that they don't like.

Ryan Holiday 8:15 Well, and, and, and this is why we don't ban books 'cause it's stupid. And, uh, it, I- it's incredibly inconsistent, right? Like the Bible is a very banned book. Uh, so, so they're, they're removing it, um, because these books have these objectionable themes. But of course, Mein Kampf is still in the pres- i- i- is still in the, uh, 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, when you, when you have chat, ChatGBT 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. 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, um, 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. And they read, and they, they spend an entire semester talking about what the Marxics- 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-

Chris Williamson 9:53 Mm.

Ryan Holiday 9:53 ... and 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.

Chris Williamson 10:10 (laughs)

Ryan Holiday 10:10 And that this was a defense mechanism, right? And it's actually funny, there's, the Stoics talk about this too, which of course I was gonna talk about in the talk. The Stoics, uh, Seneca talks about reading like a spy in the enemy's camp. The idea is you... Do you want me to stop?

Chris Williamson 10:22 No.

Ryan Holiday 10:23 Oh, no, no. I was heard the sound.

Chris Williamson 10:24 Mm-hmm.

Ryan Holiday 10:24 Good. Good. Um, 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, 'cause 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. Um, well, you can imagine the people that are removing... Well, 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 'cause it's controversial, but then you're revoking invitations to speak from people who are criticizing that idea. Um, and it escalates. So, so they, they, um, they asked me to remove it. And then it's like, I can't... I, I felt, and I don't know if I could've made this decision early on in my life, but, uh, 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-

Chris Williamson 11:55 Mm-hmm.

Ryan Holiday 11:56 ... 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 wanna keep talking here, we'd like you not to speak about the things that were..."... trying to sweep under the rug. And so I said, "You know, I can't do that." And so, of course, the invitation was revoked, and then so was the subsequent invitation. Um, the interesting thing about it to me was I, I said, you know, "I think you think this will avoid controversy, but it's only gonna do the opposite." Not only is it gonna do the opposite because, like, this is a public even- like, not, this is a, a, uh, publicized event that has now ended, you know, 10 minutes before it's supposed to go on. But, you know, part of the, like, I was speaking, eh, the, the, I was speaking at, at, I 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, 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, uh, robots that you send in to do... But that's, that's what gets countries and, uh, the world into trouble. Like, uh, the, the crown jewel of the American military, uh, and the Western militaries for c- centuries has been the ability of their leaders to think, to, uh, challenge orders, and to question, right? Th- 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, uh, "We might say that, but we don't mean it."

Chris Williamson 14:18 Mm-hmm.

Ryan Holiday 14:18 Right? Like, like, imagine you become a multi-star admiral of the Naval Academy, one of the, you know, crown s- and then you're not just a party to removing books from the library, but then you are... Like, what, what, I guess, this, this is a theme of, that I've been writing about for these last couple years is, like, what is the point of power, influence, success, a platform if you don't use it?

Chris Williamson 14:46 Mm-hmm.

Ryan Holiday 14:47 And so, uh, it was, uh, it was a s- it was a strange, surreal experience that's only sort of gotten worse. Like, the West Point just revoked an invitation, uh, and an award they were gonna give to Tom Cr- to Tom Hanks this week, um, because of his political views. So, we are in this full sway of, like, the pendulum of cancel culture, snowflake-ism-

Chris Williamson 15:08 Mm-hmm.

Ryan Holiday 15:08 ... has gone from, like, this way to this way.

Chris Williamson 15:11 Mm-hmm. And it's the same thing that's happening, just in the opposite direction.

Ryan Holiday 15:14 Yeah, and it's equally stupid in both directions, and it doesn't help anyone. Um, and then, you know, it was funny 'cause 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.

Chris Williamson 15:32 Yeah.

Ryan Holiday 15:32 I'm actually sure most of the books are bad. Like, the, the library has hundreds of thousands of titles. It would make sense that, in fact, a large percentage of them are bad. I, I would agree that most books that are published are bad and stupid and wrong. Like, uh, that's, that's how it works. But, but a free society, you know, uh, requires the free transmission and publication of ideas, right? And so, it's a, it's a weird, it's a weird moment in time, to be sure.

Chris Williamson 16:02 You've been in the war zone, it seems.

Ryan Holiday 16:05 Well, no. As I've read the, uh, maybe- maybe an-

Chris Williamson 16:08 Glass Rebellious. Yeah.

Ryan Holiday 16:08 ... intellectual war zone. The, I think what's ironic about it is these are people who are going to at someday be sent into a real war zone, and we're nervous that they're gonna read Maya Angelou or even the most, like, offensive, stupid, wrong, you know, ass-backwards book and just be like, immediate their mind-

Chris Williamson 16:30 That's my worldview now.

Ryan Holiday 16:31 Yeah, their mind melts. They're like, uh, "Actually, this is when we would wanna find that out," you know?

Chris Williamson 16:36 Mm-hmm. Ah, okay.

Ryan Holiday 16:36 You know? (laughs)

Chris Williamson 16:36 So, read these, read these stupid books-

Ryan Holiday 16:38 Yeah.

Chris Williamson 16:38 ... see if their mind is changed, and if so, out you go.

Ryan Holiday 16:41 Yes, exactly.

Chris Williamson 16:42 You say wisdom is the most elusive of the virtues.

Ryan Holiday 16:46 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, um, it, it's, it's not just elusive in terms of its ineffability, like, it's hard to define. Um, you know, it's, it's experience, it's knowledge, it's intelligence, it's creativity, it's insight, uh, it's perspective. It's, it's all of 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, uh, 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.

Chris Williamson 17:33 Mm-hmm.

Ryan Holiday 17:33 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-

Chris Williamson 17:53 Mm-hmm.

Ryan Holiday 17:53 ... still to know, and so there is something inherently humbling about it. The, 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, not just are you humbled, uh, in that most, you know, uh-... really smart people are actually quite humble. Um, but- but the more you learn, the more you learn about all the things that you still want to learn about.

Chris Williamson 18:23 Mm-hmm. What do most people get wrong when they think about wisdom, where it comes from?

Ryan Holiday 18:29 Well, you know, like, there's some, uh, you know, um, 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. It's, of course, it's a combination of all of the above. It's like you want a base of- of knowledge. Ideally, uh, you wanna learn from all of the experiences, all the- the- the great ideas that s- 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. And 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.

Chris Williamson 19:28 Mm-hmm.

Ryan Holiday 19:28 So if you're just sort of reading up in your- your tower, so to speak, uh, you might be getting smarter, but I wouldn't say you're getting wiser. Um, and then there- there is something fundamentally stupid though about trying to learn all these lessons yourself. Right? Like, um, you go, uh... I think- I think it was, uh, Otto von Bismarck, you know, he said, uh, "Any fool can learn by experience. I prefer to learn from the experiences of others." So why- why would you want to figure something out when someone has been in your exact position before? And not just, uh, 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, uh, thing you're attempting. Like, some of the smartest people who have 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 learn that which you think you already know, but- but it- it- it- it keeps you hungry to learn more and more.

Chris Williamson 20:51 I have this idea about unteachable lessons.

Ryan Holiday 20:53 Yeah.

Chris Williamson 20:53 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 storytelling.

Ryan Holiday 21:11 Yeah.

Chris Williamson 21:11 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.

Ryan Holiday 21:21 Yeah.

Chris Williamson 21:21 You know, these things that are cliché, and the reason that they're cliché is that they seem to be so reliably groundbreaking to everybody when they arrive there, so it almost becomes its own... It's like a self-defeating prophecy-

Ryan Holiday 21:38 Mm-hmm.

Chris Williamson 21:39 ... 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- 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.

Ryan Holiday 22:03 But the funny thing about that is I think one of the reasons those lessons are so cliché, and then why, uh, we talk about them so much, is partly because... Okay, so you take something like money won't make you happy, or fa- fame is empty, or you know, you're not gonna fill that hole in your soul by achieving and doing. Um, that's, you know, a theme in literature and art and- and of course social psychology also. And- and there's probably some evolutionary reasons why that's a hard lesson to learn, right? This is what propels humanity forward.

Chris Williamson 22:39 Mm-hmm.

Ryan Holiday 22:40 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.

Chris Williamson 22:55 What was Alexander's realization around that point?

Ryan Holiday 22:57 Well, I'm just saying Alexander gets all the way to the end of the world-

Chris Williamson 23:00 Mm-hmm.

Ryan Holiday 23:00 ... and- and his men are like, "How much longer are we gonna do this?" And he says, "You know, let it be said that you turned around here and, you know, didn't conquer the rest of the world with Alexander." And then he subsequently dies. And he dies this brutal, painful death where some- some of the theories are like he- he was like sort of in this like conscious coma where he's like frozen, but like... He- it was a- 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?

Chris Williamson 23:29 Wow. Mm-hmm.

Ryan Holiday 23:30 And so my- my- 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. Like I- I- 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...

Chris Williamson 23:48 The whispers just get louder and louder.

Ryan Holiday 23:49 Yeah, do you wanna hear it... Do you wanna 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?

Chris Williamson 24:14 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.

Ryan Holiday 24:21 Yes. And, and that, 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 a lesson. And p- so part of, part of why you, you take in, especially early on, why these classic, uh, myths, and ideas, and the Western canon is so important, is that they contain, from the Bible to the Odyssey, uh, you know, to Marcus Aurelius, and Aristotle, and, and, and all the great stories, is they contain kind of the sum total of human wisdom.

Chris Williamson 24:57 Mm-hmm.

Ryan Holiday 24:58 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.

Chris Williamson 25:06 Oh, there's that thing.

Ryan Holiday 25:08 That's ... Yes. And, and so you need to, you need to, you, you need to have the ideas to match with the experiences, that n- neither is, is, is sufficient on its own.

Chris Williamson 25:20 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 medal syndrome, you think, "Ah, two."

Ryan Holiday 25:40 Yes.

Chris Williamson 25:40 Two. That's the issue. The issue is I need to prove that I wasn't lucky, that I was good.

Ryan Holiday 25:44 Yes.

Chris Williamson 25:45 I don't just sell the one company for $100 million, I've gotta run it back again-

Ryan Holiday 25:49 Yeah.

Chris Williamson 25:49 ... in a different industry, and then the thing. As opposed to, no, this is habituation, you have learned this before. It's the exact same gremlin, just coming at you from a slightly more conniving angle.

Ryan Holiday 26:01 Yes.

Chris Williamson 26:02 Um ...

Ryan Holiday 26:03 And, 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 a- and, and there was a time when we had enough shared sto- that first off, there were just fewer stories, so everyone could kind of recognize, oh, this is like, you know, Odysseus-

Chris Williamson 26:21 Hamlet.

Ryan Holiday 26:21 ... at the Sirens, or this is Hamlet, or this, this is, this is, uh, you know, George Washington at this moment. You know, y- 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, a little story, a, a, a, an utterance of a few words that help you unlock the lesson, or the, the fatal flaw, or the, the, the brilliant genius of this person.

Chris Williamson 26:56 Mm-hmm.

Ryan Holiday 26:57 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 the 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, 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-

Chris Williamson 27:41 Mm-hmm.

Ryan Holiday 27:41 ... but they were illustrating something about the human experience that we need to remember.

Chris Williamson 27:47 Mm-hmm.

Chris Williamson 27:48 I was spending time with an impressionist a couple of weeks ago, and-

Ryan Holiday 27:52 Like a comedian?

Chris Williamson 27:53 Y- uh, yeah. Yeah, yeah, yeah.

Ryan Holiday 27:54 Or, or do you mean a painter?

Chris Williamson 27:55 No, sorry. Yeah, yeah.

Ryan Holiday 27:56 (laughs) .

Chris Williamson 27:56 Good, good. But he, he does impressions.

Ryan Holiday 27:57 Yeah.

Chris Williamson 27:57 Whatever that person's called.

Ryan Holiday 27:58 Yeah. If-

Chris Williamson 27:59 Are they both called the same thing?

Ryan Holiday 28:00 I think so, yeah.

Chris Williamson 28:00 Someone should change it.

Ryan Holiday 28:01 Yeah.

Chris Williamson 28:02 Um, anyway, and I was explaining, "I've got Matthew McConaughey coming back on the show."

Ryan Holiday 28:06 Yeah.

Chris Williamson 28:06 That w- wouldn't that be exciting? And, uh, he's like, "What was it like to sit down with him the first time?" And I said i- all of the thing, he's very charismatic and all the rest of it, and he does a great McConaughey. Uh, 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 ..." S- s- s- he sort of like, as if there's a little bit of straw or something-

Ryan Holiday 28:28 Yeah. Sure.

Chris Williamson 28:28 ... that he needs, and he does this with his hand. And the dude was like, "That's the unlock."

Ryan Holiday 28:33 Yeah.

Chris Williamson 28:33 And he explained to me that in the art of doing impressions of people-

Ryan Holiday 28:37 Mm-hmm.

Chris Williamson 28:37 ... uh, there is a, uh, an unlock, and the unlock is this one thing, the way that you speak, the pron- pronunciation of the S, the, uh, moving of the fingers, the hands, the face, whatever. He says that's the thing that people hook onto in the same way as what you're talking about here, is that there are these portable stories, as Clay Herbert calls them, these individual, maybe even a tiny little aphori- three-word aphorism-

Ryan Holiday 29:02 Mm-hmm.

Chris Williamson 29:02 ... whatever, um, and you go, "That's the thing." And b- both me and you, uh, quote other people a good bit-

Ryan Holiday 29:09 Yeah.

Chris Williamson 29:09 ... because original thinking's pretty tough, and also people way smarter than me and you have already figured stuff out-

Ryan Holiday 29:16 Yeah.

Chris Williamson 29:16 ... and it's kind of our job to-

Ryan Holiday 29:18 Sure.

Chris Williamson 29:18 ... essentialize that and, and, and make it accessible.

Ryan Holiday 29:20 If I could say it better, I would.

Chris Williamson 29:22 Yeah, (laughs) true, and I've tried. Um, and I think that, you know, in many ways, for me, the reason that I love it is that, um, using small quotes, aphorisms, mantras, stuff like that, is kind of like a WinZip file-

Ryan Holiday 29:36 Mm-hmm.

Chris Williamson 29:36 ... that condenses down this big thing. My memory's not that good, but it's not bad if I just have to remember th- this small sequence-

Ryan Holiday 29:43 Sure.

Chris Williamson 29:43 ... and I go, "Oh, yeah, uh, 'The universe is change, 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-

Ryan Holiday 29:54 Yes.

Chris Williamson 29:54 ... 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.

Ryan Holiday 29:59 Yeah, and, and I think too many people have confused, uh, you know, history and trivia. Exactly what year this happened, exactly how the name is pronounced, you know, exactly, you know, uh-... where the troops were aligned in this battle or that battle, um, 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, 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, th- 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, uh, basically undefended. 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, a small, uh, you know, troop of Roman, uh, Roman auxiliaries, uh, and, you know, frees the Roman army, saves Rome, uh, and is now dictator. And he, uh, after 17 days, resigns, uh, the dictatorship and returns to his farm, right? This is the plot of Gladiator, of course, uh, and it's also the model for George Washington resigning his commission after the Revolutionary War. Um, you know, uh, when King George hears that, that, uh, Washington is gonna 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 a, 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, um, but Cincinnatus almost certainly did not exist. 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.

Chris Williamson 32:19 Mm-hmm.

Ryan Holiday 32:19 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 G- you know, "Cincinnatus didn't really exist," or, "This didn't happen," or, "It was more complicated than that." Um, and look, if you're a, a grad student specializing in that thing, perhaps that is important, 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 tr- tr- continuing this tradition and the peaceful transfer of power.

Chris Williamson 33:21 Mm.

Ryan Holiday 33:21 And so the, the history is supposed to be the sort of sacred, hard-earned knowledge, uh, that we pass on from person to person. And so a lot of these famous stories, you know, maybe they're true, maybe they're not. If, if you're being literal about them, you're missing the point.

Chris Williamson 33:42 Did you read Derek Sivers' book Useful Not True?

Ryan Holiday 33:44 No. (laughs)

Chris Williamson 33:45 Okay. So I had this idea for... I swear to God I came up with it independently, (laughs) which was, uh, figuratively true, literally false.

Ryan Holiday 33:52 Yes.

Chris Williamson 33:53 Literally true, figuratively false.

Ryan Holiday 33:55 Yes.

Chris Williamson 33:55 And Derek came up with something that was n- not too dissimilar, which is usually a good idea.

Ryan Holiday 33:59 Yeah.

Chris Williamson 33:59 Like, it's like, "Hey, two people pointed at the same thing from different angles?"

Ryan Holiday 34:02 Yeah.

Chris Williamson 34:02 Like, c- d- th- might be something here.

Ryan Holiday 34:04 Sure.

Chris Williamson 34:04 Um, literally true, figuratively false, uh, you, uh, determinism might be, uh, a way to look at this, that, uh, perhaps we- 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...

Ryan Holiday 34:23 What would you do with that energy?

Chris Williamson 34:24 ... it's fucking useless.

Ryan Holiday 34:25 Yeah.

Chris Williamson 34:25 It makes me nihilistic, it makes me feel like I- I- I don't have any control over my future. Uh, something which is literally false but functionally true, um, in the, uh, Middle East in sort of medieval times, pigs are morally dirty creatures. They're no more or less moral than another cre- other creature, but in a hot climate their flesh contains more pathogens on average.

Ryan Holiday 34:47 Sure.

Chris Williamson 34:48 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 c- 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, g- 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-

Ryan Holiday 35:23 Yeah.

Chris Williamson 35:23 ... that existed, because there was stuff that was, uh, literally false, functionally false, and that n- actually needed to fuck off.

Ryan Holiday 35:29 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 it, this is important, like-

Chris Williamson 35:44 "I'm gonna arrive at it myself."

Ryan Holiday 35:46 Yeah. I, I think for myself, I'm, uh, I, I'm a first principles thinker, I, I, uh, uh-

Chris Williamson 35:52 "Not one of the sheeple, I'm autonomous."

Ryan Holiday 35:53 ... I, 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, uh, and unsustainable to, to truly think, you know, from first principles in everything, but yeah, sometimes, um, things are......incidentally solving one problem and also solving another problem-

Chris Williamson 36:25 Mm-hmm.

Ryan Holiday 36:25 ...where things are, uh, variables are, are hopelessly tied up with each other. So you, you, you go, "Hey, we don't need this. This is stupid."

Chris Williamson 36:32 Mm-hmm.

Ryan Holiday 36:32 And you don't understand because you don't have 20 years or 50 years or 1,000 years of experience in this thing that actually this is a subpar solution or an inelegant solution to a very complicated or, or multifaceted thing. And so there... 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, uh, is, is naive." Like, do you know the story of the Gordian Knot?

Chris Williamson 37:12 No.

Ryan Holiday 37:12 So there, there's this, uh, knot that's tied that is impossible to untie, and person after person, uh, goes to, 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's this, again, this sort of, uh, fetishizing of, like, these, uh, complete solutions to things that... Hey, th- the people before were not idiots.

Chris Williamson 37:51 Mm-hmm.

Ryan Holiday 37:51 And in fact they had a little more, uh, 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-

Chris Williamson 38:34 Mm-hmm.

Ryan Holiday 38:34 ...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.

Chris Williamson 38:50 You don't get to be wrong that much before there's a catastrophic outcome.

Ryan Holiday 38:53 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.

Chris Williamson 39:36 Mm-hmm.

Ryan Holiday 39:36 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 transferrable, and a lot of it is not. And, and the wisdom is knowing what domain expertise is transferrable and what isn't.

Chris Williamson 40:04 You write fantastic songs, wonderful lyricist, great at melodies-

Ryan Holiday 40:09 Yeah.

Chris Williamson 40:10 ...don't care what you think about climate change.

Ryan Holiday 40:12 Yeah.

Chris Williamson 40:12 Don't care what you think about the Ukraine. Don't care... Like you're j- 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.

Ryan Holiday 40:23 Yeah.

Chris Williamson 40:23 But just because you're great at this one thing-

Ryan Holiday 40:25 Yes.

Chris Williamson 40:25 And so I, I agree, uh, but as with most things, uh, the devil is in the details-

Ryan Holiday 40:31 Sure.

Chris Williamson 40:32 ...here. So for instance, there are people from outside of an industry-

Ryan Holiday 40:39 Yes.

Chris Williamson 40:39 ...that get a new perspective because of the fact that they're alien to this thing-

Ryan Holiday 40:44 Yeah.

Chris Williamson 40:44 ...because they see something with a, 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.

Ryan Holiday 40:54 Sure.

Chris Williamson 40:55 So I think balancing this Chesterton's fence-pilled, "Okay, let's be careful with what we get rid of"-

Ryan Holiday 41:01 Yeah.

Chris Williamson 41:02 ...like, 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"-

Ryan Holiday 41:13 Yeah.

Chris Williamson 41:13 ...and, uh, balancing those two, the innovation desire with the iteration desire.

Ryan Holiday 41:18 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, uh, 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, 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?" You know, they spent hours and hours just studying how birds, uh, you know, fly. They had a scrappiness to them. They were outsiders. They were independent. 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 a, 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, uh, as part of it. So I... There's this tendency to celebrate the sort of...... brash, you know, domineering, uh, 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, 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, uh, profound... Well, I'll give you two sort of related reformers. You have Abraham Lincoln, and then you have, uh, Thomas Clarkson, the two basically forerunners of- of- o- uh, the- the abolitionist movement. Thomas Clarkson in the UK, uh, l- leads to the- the- the eradication of the slave trade and then slavery in England, and then- then, uh, Abraham Lincoln ends it in the United States. Both of them start their campaigns against slave... They had this, 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- 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 preserve and protect slavery, actually wasn't true.

Chris Williamson 44:14 Mm.

Ryan Holiday 44:14 Thomas Clarkson, his genius is, he realizes that slavery is actually just, like, bad as a business. Like, he studies the insurance claims that slave, uh- uh, traders are making on the- the human ca- uh, cargo that they are transporting. He's looking at the fact that, like, 20% of the sailors are dying on each voyage. He- he's actually going and looking at what a slave ship looks like and then he draws his famous draw- diagram that, like, illustrates the vividness of- of what was an abstract problem before. So- so the point is, um, it's not that you have to absorb the- the dominant view or the status quo, but you have to understand the logic of why it is that way. This is where justice and wisdom are- 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 'cause, 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... if- if we were in their condition." Meaning, he's like, "If you were raised in the South-

Chris Williamson 45:40 Mm-hmm.

Ryan Holiday 45:41 ... and this is what you were taught from day one, you would think about it this way."

Chris Williamson 45:44 Mm-hmm.

Ryan Holiday 45:44 And so, uh, what- what you have to have the negative capability to understand, and for people that don't know, that's uh, uh, uh, 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 gonna change what I know to be true, or that's not gonna 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.

Chris Williamson 46:23 Mm.

Ryan Holiday 46:24 Like, Elon Musk is right, the federal government is very inefficient. Uh, and- 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, uh, obstacles and difficulties that I think he thought he could overwhelm with sheer force.

Chris Williamson 46:45 Do you know a Sam Coccos from Levels?

Ryan Holiday 46:47 No.

Chris Williamson 46:48 You know Levels, it's like a- a glucose monitor thing?

Ryan Holiday 46:50 Oh yeah, yeah, I know Levels, yeah.

Chris Williamson 46:51 Okay. So he was the founder of Levels. He is now the CIO of the Treasury Department.

Ryan Holiday 46:57 Yeah.

Chris Williamson 46:58 I'm interviewing him on Thursday. We've got an episode with him on Thursday. It's the first long-form conversation anybody from Doge has been permitted to have, and it's been, like, it's okay to happen.

Ryan Holiday 47:09 Yeah, yeah.

Chris Williamson 47:09 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- 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-

Ryan Holiday 47:36 Yeah.

Chris Williamson 47:37 ... the government into efficiency?

Ryan Holiday 47:39 Yes.

Chris Williamson 47:39 And how much of it is this ossified, walnut-shelved, mahogany, leather, fucking Chesterfield sofa bullshit that's getting in the way?

Ryan Holiday 47:47 Yeah.

Chris Williamson 47:47 And I think that's gonna be-

Ryan Holiday 47:48 And then- and- and then how much of it is there because that is the, uh, best solution to an imperfect situation? And do you have the humility and the openness, uh, and the- the, uh, empathy to understand that that's, uh, why it is that way?

Chris Williamson 48:09 Does that suggest that along with wisdom comes a, um, a ti- a humble comportment sort of gets brought in for the ride as well, that an- an amount of humility, uh, grows with the more that you are wise?

Ryan Holiday 48:26 I think so. I think so. Um, you know, uh...Epictetus said one of the signs that you're making progress in the path to wisdom is that you get in fewer arguments.

Chris Williamson 48:38 Mm.

Ryan Holiday 48:39 And, and I don't think that means that you, you know, just roll over all the time. Uh, 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, a- as I get older, I have, I d- 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, uh, they're right. They like that.

Chris Williamson 49:09 Mm-hmm.

Ryan Holiday 49:10 You know? And I'm spending a lot of my energy trying to explain why they shouldn't like that, as if it changes or means anything.

Chris Williamson 49:17 Mm-hmm.

Ryan Holiday 49:17 And so, uh, pa- 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, uh, removing yourself from most of the contentious and complicated parts of life, right? Uh, 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, 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-

Chris Williamson 49:53 Mm-hmm.

Ryan Holiday 49:53 ... accomplish and do and contribute? That's a, that's a diff-

Chris Williamson 49:56 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?

Ryan Holiday 50:07 Well, you could have, it, i- if it always goes that way, you'll be fine. But it's not always gonna go that way.

Chris Williamson 50:13 A kind of fragility, a certain kind of fragility, yes.

Ryan Holiday 50:14 Yes, yes. And so resilience, uh, adaptability, you know, uh, being able to function and contribute and perform is the ability to, to work in less than ideal environments-

Chris Williamson 50:26 Mm-hmm.

Ryan Holiday 50:26 ... with less than ideal people.

Chris Williamson 50:27 Mm-hmm.

Ryan Holiday 50:28 Um, and, and that's a, I think a skill you cultivate and develop over time.

Chris Williamson 50:33 Given that we've got modern culture of shortcuts, life hacks-

Ryan Holiday 50:37 (laughs) .

Chris Williamson 50:37 ... how do you convince people that, uh, wisdom is worth a long, uncomfortable path?

Ryan Holiday 50:46 The thing is, at, 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 want to 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, on, about wisdom is that it's not something you're born with. There are certainly people who are wiser than others.

Chris Williamson 51:31 Mm.

Ryan Holiday 51:32 But I don't think any of them came out of the womb that way.

Chris Williamson 51:34 Which is what distinguishes it from something like raw intelligence.

Ryan Holiday 51:38 Yes, yes.

Chris Williamson 51:38 Compute power.

Ryan Holiday 51:39 Yeah. Wi- wisdom is something you accumulate over time. And so if you're gonna want to 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, the fetishizing of, of, of like gurus and teachers who can just tell you everything you need to know. "Watch this video and, uh, you know, they'll tell you everything you need to know." Or, you know, "Come to this seminar." Um, 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 things. And instead, this guy, uh, acquires a, a number of wealthy slaves. Or sorry, this wealthy Roman, uh, 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 the shortcut. Until, uh, one of the men comes up to him and says, you know, "Hey, uh, this is a great party, you're ver- uh, love this repartee." He says, "Have you ever thought of, of taking up wrestling, competing in a wrestling competition?" And he goes, "Wrestling? I'm, uh, 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 for you also. And, and I think we, we are under the impression, for instance, that like, uh, artificial intelligence is this magical, transformative thing because it contains all this knowledge.

Chris Williamson 53:18 Mm-hmm.

Ryan Holiday 53:19 Um, 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 w- 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. A- a- and you can really only do that from the work. It can help you solve some problems, but if you can't recognize a good solution from a bad solution or bullshit from, from, from, from a real insight, it's not gonna do much for you. And I, 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.

Chris Williamson 54:05 Mm-hmm.

Ryan Holiday 54:05 And it almost never works.

Chris Williamson 54:08 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 over and over again, and his chauffeur, uh, was there at every single lecture that he gave.

Ryan Holiday 54:23 Yeah.

Chris Williamson 54:23 And after a while, the chauffeur basically knew the lecture off by heart.

Ryan Holiday 54:27 They give it-

Chris Williamson 54:27 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.

Ryan Holiday 54:37 Yeah.

Chris Williamson 54:37 And somebody at the end asks a question and says, "Excuse me, I, I, I just need to ask you about this." He says, "That is a question that's far too difficult for me, you're gonna have to ask my chauffeur."

Ryan Holiday 54:45 (laughs) .

Chris Williamson 54:46 And turns to the chauffeur that's the real guy.

Ryan Holiday 54:48 Yeah. Yeah, to know by heart is not to know.

Chris Williamson 54:50 Well, Naval, Naval came on the show at the start of the year and-... just this lovely idea, which is there's a big difference between appearing wise and being wise-

Ryan Holiday 54:58 Mm-hmm.

Chris Williamson 54:58 ... and the temptation to rote memorize things that give the allure, the illusion of wisdom.

Ryan Holiday 55:06 Yeah.

Chris Williamson 55:06 Like, this looks like being wise because it is an insight that someone far smarter than me came up with.

Ryan Holiday 55:12 Sure.

Chris Williamson 55:13 Uh, the difference between being able to put that out, and that's not necessarily a bad thing. It's like, right, okay, I, I understand and have retained the concept. That's a very good first start because without understanding it and retaining it, write down, write down, write down, uh, y- 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?

Ryan Holiday 55:43 Yes. Yeah, uh, to even recognize that there was a kernel of insight or truth in the idea is no-

Chris Williamson 55:50 Mm-hmm.

Ryan Holiday 55:51 ... is not nothing.

Chris Williamson 55:52 Mm-hmm.

Ryan Holiday 55:52 Uh, 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, uh, it's also why it's a loop because there are some things, you know, maybe narrative nonfiction or whatever, um, travel book or something, you read it once and you're like, "I get, I get the argument. I get, I get what I'm supposed to take from this." And then many of the great texts, uh, literature, philosophy, uh, plays, stories, poems, et cetera, you have to read, have experiences, read again, have experiences because, um, every vantage point that you look at it from, uh, particularly with the passage of time, allows you to unlock something new in it.

Chris Williamson 56:44 McConaughey says w- when he's reading a script that he reads it when he's tired, when he's happy, when he's hungover.

Ryan Holiday 56:51 Yeah.

Chris Williamson 56:51 And each time that he reads it, 'cause you don't have the luxury of taking five or 25 years to go back to fucking-

Ryan Holiday 56:58 Yeah.

Chris Williamson 56:58 ... Crime and Punishment or whatever. Uh, you need short period, "Okay, so how can I change my state-"

Ryan Holiday 57:03 Yeah.

Chris Williamson 57:03 "... so that that different perspective that I'm coming in from, that different vantage point, I get access to?"

Ryan Holiday 57:07 Yeah, that, that makes a lot of sense. Y- y- there are books that you, there are books, you know, people go, "Oh, I read that." And it, 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.

Chris Williamson 57:22 Mm-hmm.

Ryan Holiday 57:23 And this was easier to do in the ancient world 'cause 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 Hero exposed 'cause there's not any other, you know, major works to draw on. We have this, uh, 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. That's our, our blessing and our curse.

Chris Williamson 57:55 Well, I think that's a, a, a really interesting challenge that we're facing. 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, I, I had geographically triangulated who I am and why I'm here at this point.

Ryan Holiday 58:14 Yeah.

Chris Williamson 58:14 And then they go through a period of protracted challenge, uh, 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-

Ryan Holiday 58:32 Yeah.

Chris Williamson 58:33 ... uh, arrives them at a port that they have no idea-

Ryan Holiday 58:38 Yeah.

Chris Williamson 58:38 ... where the ships sail to. So, uh, what do you think, uh, a wise Stoic would say about somebody who's lost themselves in life?

Ryan Holiday 58:47 Yeah, it's, it, it, 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 'cause you don't, you don't have anything. So, uh, I think you go... Maybe one of the things you do is you go back to those things that were formative to you at one point. And I- I've been thinking a lot now about, like, what I'm rereading, what I'm rewatching, what I am reexamining because now that I am different, now that I am in different places, what I, what I, what strikes me about them as so different. Uh, 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 The Great Gatsby for the first time-"

Chris Williamson 59:37 Mm-hmm.

Ryan Holiday 59:38 "... 'cause 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 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, uh, 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, A Notebook, she says, "Well, why did I, why, why do I do this? Is it a professional, like, Rolodex? Is this, like, um, someday I'll find a story to put this quote in?" And then she said, "No, that's, that's, uh, it's gotta be more than that." 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."

Chris Williamson 1:00:47 Mm-hmm.

Ryan Holiday 1:00:47 And there's something very powerful about journaling. Like, I have this journal that I do every day where, um, 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 were doing, what you were 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 it's kinda cool, and the second year it's kinda cool, but by three, four and five, it's very powerful, 'cause you're like, "Oh, you know, in September of 2022, this is what I was thinking about." And that feels very urgent and important, or that feels, like, silly and weird.

Chris Williamson 1:01:21 Crazy.

Ryan Holiday 1:01:21 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.

Chris Williamson 1:01:36 Mm-hmm.

Ryan Holiday 1:01:36 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?

Chris Williamson 1:01:46 Mm-hmm.

Ryan Holiday 1:01:46 And, uh, 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. You've been monitoring it-

Chris Williamson 1:02:03 Tracking it.

Ryan Holiday 1:02:04 ... and tracking it incrementally as you go.

Chris Williamson 1:02:06 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.

Ryan Holiday 1:02:15 Yes.

Chris Williamson 1:02:15 Like- like that moment when you are caught up in the rumination cycle, the worry, the despair, the depression, the anxiety, the concern, uh, and- and although people unfortunately don't tend to journal when this is happening, the elation-

Ryan Holiday 1:02:29 Mm-hmm.

Chris Williamson 1:02:29 ... the bravado, the overconfidence.

Ryan Holiday 1:02:31 Yeah, the ephemerality of all of it. Like, uh, this is from Buddha, but- but this- this 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.

Chris Williamson 1:02:47 Mm-hmm.

Ryan Holiday 1:02:47 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-

Chris Williamson 1:03:03 Torture.

Ryan Holiday 1:03:03 ... it can be true of happiness, torture. All- all of it lasts, uh, longer... uh, less long than you think it does, and eventually it all does end. Like, uh, it ends one way or another, the Stoics say. Like- like you're f- 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 'cause it's going to kill you, or it's gonna 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.

Chris Williamson 1:03:45 I was reading Unbroken about Zamperini.

Ryan Holiday 1:03:49 Mm-hmm.

Chris Williamson 1:03:50 And, uh, I'd never read that so, uh, my favorite stories are kind of solo or group people against the odds.

Ryan Holiday 1:03:57 Yeah.

Chris Williamson 1:03:57 Endurance by Alfred Lansing. Uh, Forgotten Highlander by Alistair Urquhart-

Ryan Holiday 1:04:02 Yeah, yeah, I read that. Yeah.

Chris Williamson 1:04:02 ... that I got you onto. Uh, uh, and, uh, Unbroken, Laura Hillenbrand.

Ryan Holiday 1:04:07 Mm-hmm.

Chris Williamson 1:04:07 By, uh, about Louis Zamperini. And, uh, I said this to you last time, no one's done a good Stockdale book yet, have they?

Ryan Holiday 1:04:14 I'm in the works.

Chris Williamson 1:04:15 No way.

Ryan Holiday 1:04:16 Mm-hmm.

Chris Williamson 1:04:16 Let's fucking go-

Ryan Holiday 1:04:17 Yeah.

Chris Williamson 1:04:17 ... dude. Let's go.

Ryan Holiday 1:04:18 I'm, uh, I am maybe three chapters in. Uh, I've- I've been-

Chris Williamson 1:04:22 That's gonna be the next one?

Ryan Holiday 1:04:23 That's, uh-

Chris Williamson 1:04:24 One of them?

Ryan Holiday 1:04:24 So Wisdom is this, and then that's- that's the next one. I've- I-

Chris Williamson 1:04:28 So perfect.

Ryan Holiday 1:04:29 His story is fucking incredible. Like, so much better than you would think it is. Like, I think people think... Can we nerd out about Stockdale?

Chris Williamson 1:04:38 Yeah, yeah, yeah, bring it on.

Ryan Holiday 1:04:39 Okay, 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. Um, horrendously tortured. Okay, so the key to understa- like, it's not... It- it's actually a much more powerful story than even Unbroken, because, um, Zamperini, I think I'm saying that right, is- is your ordinary prisoner of war, right? He is, uh, an enemy combatant held against his will, right?

Chris Williamson 1:05:14 Mm-hmm.

Ryan Holiday 1:05:14 So, Stockdale is in, effectively, a re-education prison, right? Like the- the job is to- to take these people, to break them, and to turn them into propaganda ass- uh, assets. Okay, 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 has begun under effectively false pretenses. So, when he is shot down, uh, several months later, and he's pre- 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 see his- see his family for, you know, however long. He possesses the most terrible secret that you could possibly possess, other than perhaps knowing the nuclear codes, or the-

Chris Williamson 1:06:06 Mm-hmm.

Ryan Holiday 1:06:06 ... 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... I- because the- the- 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- who saw his country do something wrong, 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 S-16." He possesses the most significant secret of... A- and- and, um...... uh, you know, piece of information. So-

Chris Williamson 1:07:02 Like he has a very special sort of artillery shell hidden inside of his brain.

Ryan Holiday 1:07:06 Yeah.

Chris Williamson 1:07:06 And that can be deployed by people who would really like that specific weapon.

Ryan Holiday 1:07:10 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. Uh-

Chris Williamson 1:07:24 He's the bad guys.

Ryan Holiday 1:07:24 Fighting... Yeah, he is, he is, he is not, uh, fighting... It-It's a, it's, it's, it's a morally complicated war.

Chris Williamson 1:07:33 He doesn't have, he doesn't have pure virtue to stand on top of.

Ryan Holiday 1:07:36 Yes, yes. And he, and so he has to bear the weight of this.

Chris Williamson 1:07:39 It's a flimsy position to hold.

Ryan Holiday 1:07:40 Yes. And so what is he cl- 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-He's betraying... It's, he's not worried about protecting Lyndon Johnson, right? He's worried about the person in the cell next to him.

Chris Williamson 1:08:07 Mm-hmm.

Ryan Holiday 1:08:07 And so the, the, the, the m- mental gymnastics and the moral injury and weight that this guy has is unfathomable if you think about-

Chris Williamson 1:08:18 Right, yeah.

Ryan Holiday 1:08:18 ... what he's dealing with.

Chris Williamson 1:08:19 Whereas when you look, when you look at Alex Urquhart from The Forgotten Highlander, d-dysentery for four years straight.

Ryan Holiday 1:08:26 Yeah.

Chris Williamson 1:08:26 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.

Ryan Holiday 1:08:33 Yes.

Chris Williamson 1:08:33 Hardcore shit.

Ryan Holiday 1:08:34 That's like the equivalent of just climbing Mount Everest, which is just y-you versus the elements, you versus the, the situation.

Chris Williamson 1:08:40 Battle of attrition-

Ryan Holiday 1:08:41 Yes.

Chris Williamson 1:08:41 ... that's on this sort of one plane of existence.

Ryan Holiday 1:08:44 Yes.

Chris Williamson 1:08:44 What you're saying that Stockdale had was this, like, astral-

Ryan Holiday 1:08:48 Yes.

Chris Williamson 1:08:49 ... karmic challenge that he's also fighting with.

Ryan Holiday 1:08:52 Yeah, and, and, yeah, so far I've been fascinated by his childhood. Uh, and then when he's at the Naval Academy, and this is what I've been finding out about. So when he's at the Naval Academy, as, when he's a senior, the first, uh, the, 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.

Chris Williamson 1:09:14 Mm-hmm.

Ryan Holiday 1:09:14 And so as Stockdale is this young student who's just trying to get ahead, he's watching this other guy go through this, you know, horrendous ordeal. Like, they... He had to have, like, basically guards on him because they were worried other midshipmen might kill him. Uh, a-and he... There was a, 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 had only been like 10 naval officers in hist- 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-

Chris Williamson 1:09:58 Mm-hmm.

Ryan Holiday 1:09:59 ... and crush your soul, right? That's what the, the, the, the captors in the prison are not just trying to go, "Hey, if we don't give him food and water-"

Chris Williamson 1:10:10 Mm.

Ryan Holiday 1:10:10 "... you know, will they turn on their country?" They're trying to break them as human beings.

Chris Williamson 1:10:15 Mm.

Ryan Holiday 1:10:16 Um, you know, uh, they're torturing them, they're playing mind games on... And his famous thing, Stockdale is, uh, tortured for days on end, and then they basically, in a moment, they switch. And they go, "Okay, uh, this is too much. We've, we've pushed you too far. We're sorry. Why don't you go, uh, 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 wanna clean me up." And he realizes they're about to, to parade him in front of the cameras. They want him to give a videotaped statement. Maybe they, maybe he's even sensing in this moment that they know what he knows.

Chris Williamson 1:10:56 Mm.

Ryan Holiday 1:10:57 And so at this moment, he walks into the bathroom. He says he, he knew he had about a minute in there. And he begins to beat his face to a bloody pulp, uh, with the stool. And then he cuts, he shatters the mirror and he, 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, um, uh-

Chris Williamson 1:11:23 Unspeakable, let's say.

Ryan Holiday 1:11:24 Un- Un-

Chris Williamson 1:11:24 Yeah.

Ryan Holiday 1:11:24 Yeah, he's bleeding everywhere. And, and it's like they come in, they think he's trying to kill himself, and he hasn't. He's just, just-

Chris Williamson 1:11:31 Maimed himself.

Ryan Holiday 1:11:31 Maimed himself so he is unfilmable.

Chris Williamson 1:11:34 Not press-worthy.

Ryan Holiday 1:11:35 Yeah. And, and they go, you know, you know, "What are we supposed to do? We were supposed to take you downtown." And, 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 ate- intensity-

Chris Williamson 1:11:55 Mm-hmm.

Ryan Holiday 1:11:55 ... that takes on a whole different color when you realize what he's holding and what he's been through.

Chris Williamson 1:12:01 Mm-hmm.

Ryan Holiday 1:12:01 And that, that he realizes that, yeah, it, it's about his connection to these other people, which I think is interesting. What I'm f- 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 believe when he was 20 at the Naval Academy. Th- 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 cross-country with him. And Jimmy Carter is famously like this suppor- a guy who grows up in like se- the segregated South, is there helping and encouraging this guy. And, and Stockdale's like sort of too busy doing his own thing.

Chris Williamson 1:12:47 Mm-hmm.

Ryan Holiday 1:12:47 And so I- I'm, I'm fascinated. How does this person go from like selfish in the way that when we're young, we're all, "I'm into me-"

Chris Williamson 1:12:55 Mm-hmm.

Ryan Holiday 1:12:55 "... and my thing and what I'm trying to do. I don't have time."

Chris Williamson 1:12:57 "I love me. Who do you love?"

Ryan Holiday 1:12:58 "I don't have time for this other stuff." You know? Like that, "If not, if I am not for me, who is?"

Chris Williamson 1:13:03 Mm-hmm, mm-hmm.

Ryan Holiday 1:13:04 And then he becomes, by the end, "If I am only for me, who am I?"... and that's the arc of Stockdale. So that's the book I'm writing.

Chris Williamson 1:13:11 Bro, I cannot wait for you to do that.

Ryan Holiday 1:13:13 I, I'm loving it.

Chris Williamson 1:13:14 That's it. That's sick. And I guess, Conspiracy, you're tracking a story but it's over, like, a tighter-

Ryan Holiday 1:13:20 Yeah.

Chris Williamson 1:13:20 ... timeline, right? But a lot of investigation, what's going on, but this is like archive shit. This is-

Ryan Holiday 1:13:25 Well yeah, to, 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.

Chris Williamson 1:13:32 Yeah.

Ryan Holiday 1:13:32 And I wanna... I love those kind of books.

Chris Williamson 1:13:34 Mm-hmm.

Ryan Holiday 1:13:35 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.

Chris Williamson 1:13:52 I

Chris Williamson 1:13:53 j-... I, I want to bring up a video of yours that I remember seeing. I wanna 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?

Ryan Holiday 1:14:07 I think I've done it a couple of times.

Chris Williamson 1:14:08 Okay. So there's a-

Ryan Holiday 1:14:08 I know when the call's coming in-

Chris Williamson 1:14:10 Okay. So there's-

Ryan Holiday 1:14:10 ... so I flip on the camera.

Chris Williamson 1:14:11 Yeah. The, the, there's this video... Maybe, maybe your kid's in the room, or maybe not. Anyway, and then you're, you're there, and you're talking to them and they say, "Ryan, just congratulations. Bestseller list, 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."

Ryan Holiday 1:14:30 Yes.

Chris Williamson 1:14:30 And I remember, I remember watching that and, you know, we've met... This is episode, like, seven. First time you came on this show was, like, fucking six, seven years ago or something.

Ryan Holiday 1:14:37 Really?

Chris Williamson 1:14:37 Yeah, yeah, yeah. Forever ago. Like when I was still in

Ryan Holiday 1:14:38 Oh, this is sick. I thought you were saying I was on sick. Got it.

Chris Williamson 1:14:40 No, no, no.

Ryan Holiday 1:14:40 Okay, I get what you're saying.

Chris Williamson 1:14:41 Um, so I've got like a, you know-

Ryan Holiday 1:14:43 Yeah.

Chris Williamson 1:14:43 ... good understanding of, sort of, I think, where you're at. I, I wanted to ask you about that, because 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, philosophically shallow as, "I'm just moving onto the next thing."

Ryan Holiday 1:15:12 Yeah.

Chris Williamson 1:15:12 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 that's great, that by all accounts I probably should put the fucking book 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... 'Cause I'm, I'm very interested-

Ryan Holiday 1:15:40 Yeah, yeah.

Chris Williamson 1:15:40 O- one of the criticisms, typically, of Stoicism, is sort of a, a, a, a lack of celebration of the good, this sort of, um, indifference to emotion that is good in times of strife, but kind of, like, having sex with a condom on in times of, uh, you know, in times of good. It's like a prophylactic against everything-

Ryan Holiday 1:15:58 Yeah, yeah.

Chris Williamson 1:15:58 ... unfortunately including-

Ryan Holiday 1:15:59 (laughs)

Chris Williamson 1:15:59 ... the celebrations. Um, th- did you consider taking-

Ryan Holiday 1:16:02 Yeah.

Chris Williamson 1:16:02 ... the condom off at some point?

Ryan Holiday 1:16:03 (laughs) I, I... There's a couple of things there. I think, talking about wisdom, one of the things you'll sometimes, uh, you can hear from older people is something 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 ca-" And they're like, "No, no, no, I appreciated it. You should take the compliment." And that, I think that's something that, that everyone should work on, if, with s-... If someone's saying they like something, if someone's saying, "Great job-"

Chris Williamson 1:16:26 Be gracious with it, yeah.

Ryan Holiday 1:16:26 ... be, be gracious with it because you think you're being self-effacing, but actually you're rejecting-

Chris Williamson 1:16:31 It's a middle finger to them.

Ryan Holiday 1:16:31 Yes, exactly. And I, 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 times, "and, and then you just work right back to work? Where's the joy? Where's the fun?" Um, and my answer i- i- is that the joy and the fun is not in throwing a party for hitting number one.

Chris Williamson 1:16:52 Mm.

Ryan Holiday 1:16:53 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, uh, invigorating, uh, problem to solve, and that I'm making progress on it and it's coming together, and I'm learning and I'm growing and I'm, I'm doing what I, like, am meant to do.

Chris Williamson 1:17:22 Mm.

Ryan Holiday 1:17:23 So, um, one of the hardest parts of the schedule that I am on is that usually my m- my last project is coming out when I'm in the, my favorite part of the next one-

Chris Williamson 1:17:36 Right now, which is why you're so fired up about Stockdale-

Ryan Holiday 1:17:38 Yeah.

Chris Williamson 1:17:38 ... when we should be talking about-

Ryan Holiday 1:17:39 I know.

Chris Williamson 1:17:39 ... fucking wisdom.

Ryan Holiday 1:17:39 Yeah. Like, I, I didn't really do... I, 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've gotta pick up my... So, like, I'm actually not doing the thing that I like to do. Um, 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, uh, like all people, I, I, I was somewhat extrinsically motivated al-... Like, I wanted to hit-

Chris Williamson 1:18:05 Exoteric.

Ryan Holiday 1:18:05 ... the bestsell-

Chris Williamson 1:18:06 Yeah.

Ryan Holiday 1:18:06 ... b- bestseller 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, um, I just feel like the reward for succeeding-

Chris Williamson 1:18:23 Mm.

Ryan Holiday 1:18:23 ... should not be taking away from it. Like, I'll tell you, like, my first... The first time I hit, uh, the New York Times bestseller list, uh, Stillness is the Key De-... Stillness is the Key debuted at number one in 2019. And I remember I woke up, I was in LA on book tour, and, um, I could... I, you know, my alarm goes off on my phone, and one of my rules, I don't check my phone the first thing that I do when I wake up, 'cause I, I try to-

Chris Williamson 1:18:46 But that's difficult on the road, right? Because-

Ryan Holiday 1:18:47 Yeah, exactly. It's an alarm phone.

Chris Williamson 1:18:49 ... you're using your phone as the alarm.

Ryan Holiday 1:18:50 And so, so, it's like, you know you pick up your phone and you're like, "Some stuff has happened." You know?

Chris Williamson 1:18:54 (laughs)

Ryan Holiday 1:18:54 Like, I can tell some stuff has happened. And, and, and I remember going-

Chris Williamson 1:18:58 Yeah.

Ryan Holiday 1:18:58 ... um, so I was staying at the Los Angeles Athletic Club, which is one of my favorite places to swim, and I, I go, "Okay, like, this is either good news or it's bad news about the book." 'Cause it's coming from New York, right? So I'm on the West Coast.

Chris Williamson 1:19:10 Uh, you're three hours behind.

Ryan Holiday 1:19:11 Yeah.