Why Most Smart People Become Stupid - Ryan Holiday

1. 0:00 – 5:13

   Why We Need to Push Outside Our Comfort Zone

   1. CWChris Williamson0:00

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

   2. RHRyan Holiday0:02

      Oh.

   3. CWChris Williamson0:03

      ... we were discussing your upcoming live shows.

   4. RHRyan Holiday0:05

      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.

   5. CWChris Williamson0:35

      Yeah. What's new?

   6. RHRyan Holiday0:36

      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.

   7. CWChris Williamson0:48

      Mm-hmm. Mm-hmm.

   8. RHRyan Holiday0:48

      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?

   9. CWChris Williamson0:58

      Hmm.

   10. RHRyan Holiday0:58

       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-

   11. CWChris Williamson1:04

       A huge fucking audience.

   12. RHRyan Holiday1:05

       ... is a, is a... You know, it's a whole thing.

   13. CWChris Williamson1:07

       Difficulty plus, yeah.

   14. RHRyan Holiday1:08

       Yeah.

   15. CWChris Williamson1:09

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

   16. RHRyan Holiday1:15

       Yes.

   17. CWChris Williamson1:15

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

   18. RHRyan Holiday1:18

       Yes.

   19. CWChris Williamson1:18

       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-

   20. RHRyan Holiday1:31

       Yeah.

   21. CWChris Williamson1:31

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

   22. RHRyan Holiday1:37

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

   23. CWChris Williamson1:44

       Doesn't play by your rules.

   24. RHRyan Holiday1:45

       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.

   25. CWChris Williamson2:12

       Everyone's there.

   26. RHRyan Holiday2:12

       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.

   27. CWChris Williamson2:46

       Seven minutes to go.

   28. RHRyan Holiday2:47

       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?"

   29. CWChris Williamson2:59

       (laughs)

   30. RHRyan Holiday2:59

       It's like, "Is no one talking to each other?"
2. 5:13 – 16:42

   Banning Books Isn't Ethical

   1. RHRyan Holiday5:13

   2. CWChris Williamson5:13

      Yeah. What happened with that Naval Academy-

   3. RHRyan Holiday5:18

      Oh, my God. (laughs)

   4. CWChris Williamson5:19

      ... speech?

   5. RHRyan Holiday5:19

      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.

   6. CWChris Williamson5:46

      Real-world Top Gun shit.

   7. RHRyan Holiday5:47

      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-

   8. CWChris Williamson6:18

      Mm-hmm.

   9. RHRyan Holiday6:19

      ... 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.

   10. CWChris Williamson7:18

       Okay.

   11. RHRyan Holiday7:18

       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.

   12. CWChris Williamson7:30

       Mm-hmm.

   13. RHRyan Holiday7:30

       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.

   14. CWChris Williamson7:37

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

   15. RHRyan Holiday7:43

       Mm-hmm.

   16. CWChris Williamson7:43

       So this was the inverse of that situation, that was, uh, one book, or one series of books, Harry Potter-

   17. RHRyan Holiday7:50

       Yeah.

   18. CWChris Williamson7:50

       ... uh, originally in the '90s and 2000s by right wing-

   19. RHRyan Holiday7:55

       Yeah.

   20. CWChris Williamson7:55

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

   21. RHRyan Holiday8:01

       Yeah.

   22. CWChris Williamson8:01

       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-

   23. RHRyan Holiday8:12

       Right wing ca- Yeah.

   24. CWChris Williamson8:12

       ... in the modern world, trying to get rid of books that they don't like.

   25. RHRyan Holiday8:15

       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-

   26. CWChris Williamson9:53

       Mm.

   27. RHRyan Holiday9:53

       ... 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.

   28. CWChris Williamson10:10

       (laughs)

   29. RHRyan Holiday10:10

       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?

   30. CWChris Williamson10:22

       No.
3. 16:42 – 27:48

   Does Learning Keeps Us Humble?

   1. RHRyan Holiday16:42

   2. CWChris Williamson16:42

      You say wisdom is the most elusive of the virtues.

   3. RHRyan Holiday16:46

      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.

   4. CWChris Williamson17:33

      Mm-hmm.

   5. RHRyan Holiday17:33

      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-

   6. CWChris Williamson17:53

      Mm-hmm.

   7. RHRyan Holiday17:53

      ... 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.

   8. CWChris Williamson18:23

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

   9. RHRyan Holiday18:29

      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.

   10. CWChris Williamson19:28

       Mm-hmm.

   11. RHRyan Holiday19:28

       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.

   12. CWChris Williamson20:51

       I have this idea about unteachable lessons.

   13. RHRyan Holiday20:53

       Yeah.

   14. CWChris Williamson20:53

       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.

   15. RHRyan Holiday21:11

       Yeah.

   16. CWChris Williamson21:11

       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.

   17. RHRyan Holiday21:21

       Yeah.

   18. CWChris Williamson21:21

       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-

   19. RHRyan Holiday21:38

       Mm-hmm.

   20. CWChris Williamson21:39

       ... 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.

   21. RHRyan Holiday22:03

       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.

   22. CWChris Williamson22:39

       Mm-hmm.

   23. RHRyan Holiday22:40

       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.

   24. CWChris Williamson22:55

       What was Alexander's realization around that point?

   25. RHRyan Holiday22:57

       Well, I'm just saying Alexander gets all the way to the end of the world-

   26. CWChris Williamson23:00

       Mm-hmm.

   27. RHRyan Holiday23:00

       ... 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?

   28. CWChris Williamson23:29

       Wow. Mm-hmm.

   29. RHRyan Holiday23:30

       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...

   30. CWChris Williamson23:48

       The whispers just get louder and louder.
4. 27:48 – 33:42

   The Value of Learning from Others

   1. CWChris Williamson27:48

      I was spending time with an impressionist a couple of weeks ago, and-

   2. RHRyan Holiday27:52

      Like a comedian?

   3. CWChris Williamson27:53

      Y- uh, yeah. Yeah, yeah, yeah.

   4. RHRyan Holiday27:54

      Or, or do you mean a painter?

   5. CWChris Williamson27:55

      No, sorry. Yeah, yeah.

   6. RHRyan Holiday27:56

      (laughs) .

   7. CWChris Williamson27:56

      Good, good. But he, he does impressions.

   8. RHRyan Holiday27:57

      Yeah.

   9. CWChris Williamson27:57

      Whatever that person's called.

   10. RHRyan Holiday27:58

       Yeah. If-

   11. CWChris Williamson27:59

       Are they both called the same thing?

   12. RHRyan Holiday28:00

       I think so, yeah.

   13. CWChris Williamson28:00

       Someone should change it.

   14. RHRyan Holiday28:01

       Yeah.

   15. CWChris Williamson28:02

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

   16. RHRyan Holiday28:06

       Yeah.

   17. CWChris Williamson28:06

       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-

   18. RHRyan Holiday28:28

       Yeah. Sure.

   19. CWChris Williamson28:28

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

   20. RHRyan Holiday28:33

       Yeah.

   21. CWChris Williamson28:33

       And he explained to me that in the art of doing impressions of people-

   22. RHRyan Holiday28:37

       Mm-hmm.

   23. CWChris Williamson28:37

       ... 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-

   24. RHRyan Holiday29:02

       Mm-hmm.

   25. CWChris Williamson29:02

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

   26. RHRyan Holiday29:09

       Yeah.

   27. CWChris Williamson29:09

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

   28. RHRyan Holiday29:16

       Yeah.

   29. CWChris Williamson29:16

       ... and it's kind of our job to-

   30. RHRyan Holiday29:18

       Sure.
5. 33:42 – 50:33

   The Status Quo is There For a Reason

   1. CWChris Williamson33:42

      Did you read Derek Sivers' book Useful Not True?

   2. RHRyan Holiday33:44

      No. (laughs)

   3. CWChris Williamson33:45

      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.

   4. RHRyan Holiday33:52

      Yes.

   5. CWChris Williamson33:53

      Literally true, figuratively false.

   6. RHRyan Holiday33:55

      Yes.

   7. CWChris Williamson33:55

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

   8. RHRyan Holiday33:59

      Yeah.

   9. CWChris Williamson33:59

      Like, it's like, "Hey, two people pointed at the same thing from different angles?"

   10. RHRyan Holiday34:02

       Yeah.

   11. CWChris Williamson34:02

       Like, c- d- th- might be something here.

   12. RHRyan Holiday34:04

       Sure.

   13. CWChris Williamson34:04

       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...

   14. RHRyan Holiday34:23

       What would you do with that energy?

   15. CWChris Williamson34:24

       ... it's fucking useless.

   16. RHRyan Holiday34:25

       Yeah.

   17. CWChris Williamson34:25

       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.

   18. RHRyan Holiday34:47

       Sure.

   19. CWChris Williamson34:48

       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-

   20. RHRyan Holiday35:23

       Yeah.

   21. CWChris Williamson35:23

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

   22. RHRyan Holiday35:29

       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-

   23. CWChris Williamson35:44

       "I'm gonna arrive at it myself."

   24. RHRyan Holiday35:46

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

   25. CWChris Williamson35:52

       "Not one of the sheeple, I'm autonomous."

   26. RHRyan Holiday35:53

       ... 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-

   27. CWChris Williamson36:25

       Mm-hmm.

   28. RHRyan Holiday36:25

       ...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."

   29. CWChris Williamson36:32

       Mm-hmm.

   30. RHRyan Holiday36:32

       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?
6. 50:33 – 57:55

   Start the Work Now - Your Wisdom Will Thank You

   1. RHRyan Holiday50:33

   2. CWChris Williamson50:33

      Given that we've got modern culture of shortcuts, life hacks-

   3. RHRyan Holiday50:37

      (laughs) .

   4. CWChris Williamson50:37

      ... how do you convince people that, uh, wisdom is worth a long, uncomfortable path?

   5. RHRyan Holiday50:46

      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.

   6. CWChris Williamson51:31

      Mm.

   7. RHRyan Holiday51:32

      But I don't think any of them came out of the womb that way.

   8. CWChris Williamson51:34

      Which is what distinguishes it from something like raw intelligence.

   9. RHRyan Holiday51:38

      Yes, yes.

   10. CWChris Williamson51:38

       Compute power.

   11. RHRyan Holiday51:39

       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.

   12. CWChris Williamson53:18

       Mm-hmm.

   13. RHRyan Holiday53:19

       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.

   14. CWChris Williamson54:05

       Mm-hmm.

   15. RHRyan Holiday54:05

       And it almost never works.

   16. CWChris Williamson54:08

       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.

   17. RHRyan Holiday54:23

       Yeah.

   18. CWChris Williamson54:23

       And after a while, the chauffeur basically knew the lecture off by heart.

   19. RHRyan Holiday54:27

       They give it-

   20. CWChris Williamson54:27

       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.

   21. RHRyan Holiday54:37

       Yeah.

   22. CWChris Williamson54:37

       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."

   23. RHRyan Holiday54:45

       (laughs) .

   24. CWChris Williamson54:46

       And turns to the chauffeur that's the real guy.

   25. RHRyan Holiday54:48

       Yeah. Yeah, to know by heart is not to know.

   26. CWChris Williamson54:50

       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-

   27. RHRyan Holiday54:58

       Mm-hmm.

   28. CWChris Williamson54:58

       ... and the temptation to rote memorize things that give the allure, the illusion of wisdom.

   29. RHRyan Holiday55:06

       Yeah.

   30. CWChris Williamson55:06

       Like, this looks like being wise because it is an insight that someone far smarter than me came up with.
7. 57:55 – 1:03:45

   The Power of Remembering Who You Used to Be

   1. RHRyan Holiday57:55

   2. CWChris Williamson57:55

      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.

   3. RHRyan Holiday58:14

      Yeah.

   4. CWChris Williamson58:14

      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-

   5. RHRyan Holiday58:32

      Yeah.

   6. CWChris Williamson58:33

      ... uh, arrives them at a port that they have no idea-

   7. RHRyan Holiday58:38

      Yeah.

   8. CWChris Williamson58:38

      ... 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?

   9. RHRyan Holiday58:47

      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-"

   10. CWChris Williamson59:37

       Mm-hmm.

   11. RHRyan Holiday59:38

       "... '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."

   12. CWChris Williamson1:00:47

       Mm-hmm.

   13. RHRyan Holiday1:00:47

       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.

   14. CWChris Williamson1:01:21

       Crazy.

   15. RHRyan Holiday1:01:21

       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.

   16. CWChris Williamson1:01:36

       Mm-hmm.

   17. RHRyan Holiday1:01:36

       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?

   18. CWChris Williamson1:01:46

       Mm-hmm.

   19. RHRyan Holiday1:01:46

       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-

   20. CWChris Williamson1:02:03

       Tracking it.

   21. RHRyan Holiday1:02:04

       ... and tracking it incrementally as you go.

   22. CWChris Williamson1:02:06

       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.

   23. RHRyan Holiday1:02:15

       Yes.

   24. CWChris Williamson1:02:15

       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-

   25. RHRyan Holiday1:02:29

       Mm-hmm.

   26. CWChris Williamson1:02:29

       ... the bravado, the overconfidence.

   27. RHRyan Holiday1:02:31

       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.

   28. CWChris Williamson1:02:47

       Mm-hmm.

   29. RHRyan Holiday1:02:47

       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-

   30. CWChris Williamson1:03:03

       Torture.
8. 1:03:45 – 1:13:53

   How Stockdale Remained Unbroken

   1. RHRyan Holiday1:03:45

   2. CWChris Williamson1:03:45

      I was reading Unbroken about Zamperini.

   3. RHRyan Holiday1:03:49

      Mm-hmm.

   4. CWChris Williamson1:03:50

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

   5. RHRyan Holiday1:03:57

      Yeah.

   6. CWChris Williamson1:03:57

      Endurance by Alfred Lansing. Uh, Forgotten Highlander by Alistair Urquhart-

   7. RHRyan Holiday1:04:02

      Yeah, yeah, I read that. Yeah.

   8. CWChris Williamson1:04:02

      ... that I got you onto. Uh, uh, and, uh, Unbroken, Laura Hillenbrand.

   9. RHRyan Holiday1:04:07

      Mm-hmm.

   10. CWChris Williamson1:04:07

       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?

   11. RHRyan Holiday1:04:14

       I'm in the works.

   12. CWChris Williamson1:04:15

       No way.

   13. RHRyan Holiday1:04:16

       Mm-hmm.

   14. CWChris Williamson1:04:16

       Let's fucking go-

   15. RHRyan Holiday1:04:17

       Yeah.

   16. CWChris Williamson1:04:17

       ... dude. Let's go.

   17. RHRyan Holiday1:04:18

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

   18. CWChris Williamson1:04:22

       That's gonna be the next one?

   19. RHRyan Holiday1:04:23

       That's, uh-

   20. CWChris Williamson1:04:24

       One of them?

   21. RHRyan Holiday1:04:24

       So Wisdom is this, and then that's- that's the next one. I've- I-

   22. CWChris Williamson1:04:28

       So perfect.

   23. RHRyan Holiday1:04:29

       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?

   24. CWChris Williamson1:04:38

       Yeah, yeah, yeah, bring it on.

   25. RHRyan Holiday1:04:39

       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?

   26. CWChris Williamson1:05:14

       Mm-hmm.

   27. RHRyan Holiday1:05:14

       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-

   28. CWChris Williamson1:06:06

       Mm-hmm.

   29. RHRyan Holiday1:06:06

       ... 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-

   30. CWChris Williamson1:07:02

       Like he has a very special sort of artillery shell hidden inside of his brain.
9. 1:13:53 – 1:20:03

   How Ryan Celebrates His Wins

   1. CWChris Williamson1:13:53

      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?

   2. RHRyan Holiday1:14:07

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

   3. CWChris Williamson1:14:08

      Okay. So there's a-

   4. RHRyan Holiday1:14:08

      I know when the call's coming in-

   5. CWChris Williamson1:14:10

      Okay. So there's-

   6. RHRyan Holiday1:14:10

      ... so I flip on the camera.

   7. CWChris Williamson1:14:11

      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."

   8. RHRyan Holiday1:14:30

      Yes.

   9. CWChris Williamson1:14:30

      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.

   10. RHRyan Holiday1:14:37

       Really?

   11. CWChris Williamson1:14:37

       Yeah, yeah, yeah. Forever ago. Like when I was still in

   12. RHRyan Holiday1:14:38

       Oh, this is sick. I thought you were saying I was on sick. Got it.

   13. CWChris Williamson1:14:40

       No, no, no.

   14. RHRyan Holiday1:14:40

       Okay, I get what you're saying.

   15. CWChris Williamson1:14:41

       Um, so I've got like a, you know-

   16. RHRyan Holiday1:14:43

       Yeah.

   17. CWChris Williamson1:14:43

       ... 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."

   18. RHRyan Holiday1:15:12

       Yeah.

   19. CWChris Williamson1:15:12

       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-

   20. RHRyan Holiday1:15:40

       Yeah, yeah.

   21. CWChris Williamson1:15:40

       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-

   22. RHRyan Holiday1:15:58

       Yeah, yeah.

   23. CWChris Williamson1:15:58

       ... unfortunately including-

   24. RHRyan Holiday1:15:59

       (laughs)

   25. CWChris Williamson1:15:59

       ... the celebrations. Um, th- did you consider taking-

   26. RHRyan Holiday1:16:02

       Yeah.

   27. CWChris Williamson1:16:02

       ... the condom off at some point?

   28. RHRyan Holiday1:16:03

       (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-"

   29. CWChris Williamson1:16:26

       Be gracious with it, yeah.

   30. RHRyan Holiday1:16:26

       ... be, be gracious with it because you think you're being self-effacing, but actually you're rejecting-

Episode duration: 1:49:16