The Hard Truth About Character | General Stanley McChrystal (PT. 1)

We control who we are. We control what we do. We control the standards we hold ourselves to. Ryan sits down with retired four-star General Stanley McChrystal to talk about the thing that makes or breaks every person: character. They explain what character actually is, why discipline matters more than raw talent, and how great leaders can lose their way. General McChrystal is a retired United States Army general best known for his command of Joint Special Operations Command in the mid-2000s. He established a consultancy firm, McChrystal Group, in 2011 and advises senior executives at multinational corporations on navigating complex change and building stronger teams. 📚 You can grab signed copies of On Character: Choices That Define A Life https://www.thepaintedporch.com/products/on-character-choices-that-define-a-life-signed-by-author?_pos=2&_sid=6b1df1465&_ss=r by General McChrystal at The Painted Porch | https://www.thepaintedporch.com/ https://www.thepaintedporch.com/products/on-character-choices-that-define-a-life-signed-by-author?_pos=2&_sid=6b1df1465&_ss=r 🎙️ Listen to General Stanley McChrystal’s first interview on The Daily Stoic Podcast | Apple Podcasts https://podcasts.apple.com/us/podcast/general-stanley-mcchrystal-on-getting-comfortable-with/id1430315931?i=1000547642629, Spotify, https://open.spotify.com/episode/0G5kWu9qiZJyAW2WOsfCwT & YouTube https://www.youtube.com/watch?v=DIU2ANZjuJw 📖 Preorder the final book in Ryan Holiday's The Stoic Virtues Series: "Wisdom Takes Work":https://store.dailystoic.com/pages/wisdom-takes-work 🎙️ Follow The Daily Stoic Podcast on Instagram https://www.instagram.com/dailystoicpodcast/?hl=en: https://www.instagram.com/dailystoicpodcast 🎥 Watch top moments from The Daily Stoic Podcast https://www.youtube.com/@dailystoicpodcast on YouTube https://www.youtube.com/@dailystoicpodcast: https://www.youtube.com/@dailystoicpodcast ✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail 🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/ 📱 Follow us: Instagram https://www.instagram.com/dailystoic/,Twitter https://twitter.com/dailystoic,YouTube https://www.youtube.com/@DailyStoic,TikTok https://www.tiktok.com/@daily_stoic?lang=en, andFacebook https://www.facebook.com/dailystoic See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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

• 0:06Ryan Holiday?

  Welcome to the Daily Stoic Podcast where each weekday we bring you a meditation inspired by the ancient Stoics, a short passage of ancient wisdom designed to help you find strength and insight here in everyday life. And on Wednesdays, we talk to some of our fellow students of ancient philosophy, well-known and obscure, fascinating and powerful. With them, we discuss the strategies and habits that have helped them become who they are, and also to find peace and wisdom in their lives.

• 0:51Ryan Holiday?

  We don't control what's happening in the world. We don't control by and large who our leaders are. We don't control by and large what our leaders do. We don't control the ethics or the standards that other people hold themselves to. I wish it were otherwise, but it isn't. But the one thing we do control, one thing I've been thinking a lot about now, as it feels like the world has fallen apart, is we control who we are, we do, we control the standards we hold ourselves to. It comes down to character. Character, or a lack thereof, is kind of why we're in the mess that we're in, and it's going to be our way out of this

• 1:32Ryan Holiday?

  mess. I read this book on character by General Stanley McChrystal back in December, which feels like a lifetime ago. That's what living in a world of characterless leaders will do to you. There's been disasters since, there's been corruption since, there's been needless division, there's been hateful things that have happened, there have been terrorist attacks. There's been a lot, right? And I've been thinking about this book almost every day since. The subtitle is Choices That Define A Life. That's what character is. It's not anything anyone makes you do. It's not necessarily something that's even incentivized or rewarded.

• 2:14Ryan Holiday?

  You either have character or you don't. You either make character-driven choices or you don't. And so I was really excited to have General Stanley McChrystal on the podcast to talk about what felt like A throwback kind of a book. It's really a series of essays, some short, some long, all about the idea of character, what it means, how we develop it, how it challenges us, how we are challenged to live up to it. I think everyone should read this book and I am really excited to have you listen in on this conversation that I had with General McChrystal. He is best known for his Joint Special Operations Command, which he held

• 2:55Ryan Holiday?

  in the mid 2000s. After his time in Afghanistan and Iraq, he built a consultancy firm called the McChrystal Group, works with executives and Fortune 500 companies and multinational corporations, trying to help them deal with change, deal with building teams. And for all that work, this book is much more individual. This is much more about what we do as human beings, what we do with the problems, dilemmas, crises and opportunities in front of us. And I really enjoyed this conversation and I think you will enjoy listening to it. I'm going to split it up into two parts. Part one, we're going to be talking about the

• 3:36Ryan Holiday?

  evolution of character, talking about virtue and leadership and decision making and some historical examples that he and I nerd out about a little bit. And I think you're really going to like this conversation. Thanks to General McChrystal for coming out. If you haven't read his other books like Team of Teams or Risk, I think you are missing out as well. But this is my favorite of all the books he's written. And we talked before a couple of years ago about his Risk book. I really enjoyed that conversation and I think you will like it too.

• 4:07Ryan Holiday?

  Two of your books are probably on the wall in here. Did you see it?

• 4:09Speaker 01

  One of them is up there. Yeah.

• 4:10Ryan Holiday?

  Okay, so there's a company called Books by the Foot and they do it for like film sets and stuff. And so that's who we use to send them in. But then I asked Portfolio to send me a copy of every book in there.

• 4:23Speaker 01

  That's cool.

• 4:23Ryan Holiday?

  And I think so I think you should be in here at least. I don't know if Risk could come out yet.

• 4:28Speaker 01

  It's so easy to get old books now because people don't keep them like they used to.

• 4:31Ryan Holiday?

  I know. Yes. And you can tell, you can kind of see like different eras, like, oh, this person was super popular then. And so it's probably like. They died and then their kids took them to Goodwill or whatever.

• 4:42Speaker 01

  Exactly.

• 4:43Ryan Holiday?

  What am I supposed to do with dad's books, you know?

• 4:45Speaker 01

  I, my house is full of books and nobody's gonna want them.

• 4:48Ryan Holiday?

  Yes, I know, I know. It's sort of a metaphor. You like collect all this stuff and then it's, it's worth something to you and then it's not just worthless to someone. It's like less than worthless.

• 4:59Speaker 01

  Cause they gotta get rid of it.

• 5:00Ryan Holiday?

  I know. Although I just saw there was an auction. I'm into like weird antiques. It's very clear that Sherman's great grandchildren are finally getting rid of all his shit.

• 5:08Speaker 01

  Wow.

• 5:09Ryan Holiday?

  Because like there were all these like, it's like a signed copy of Grant's memoirs stamped with Sherman. And it clearly went from him to his son to his grandson. And then his great grandson's like, what am I gonna do with this?

• 5:20Speaker 01

  I've got stuff like that. And I've got my grandfather's old swords and stuff like that. And nobody is gonna want them. Hopefully one of my granddaughters will take them out of, you know, something, but.

• 5:31Ryan Holiday?

  Yeah, that was what I would have liked to have that. It's worth more to someone who's not related to you than your, your own family.

• 5:38Speaker 01

  Exactly.

• 5:39Ryan Holiday?

  Did you work out this morning at the, at the Las Vegas? Did you run or what'd you do?

• 5:43Speaker 01

  Today was a lifting day. So I do, I'm 70 now, so I do a whole bunch of, I do an hour and a half, whole bunch of abs. And then some lifting, not impressive.

• 5:52Ryan Holiday?

  Really?

• 5:52Speaker 01

  And then the other day I do, I do an hour and a half each day. The other day I do 70 minutes on an elliptical, then 20 minutes on an indoor bike.

• 6:00Ryan Holiday?

  Wow.

• 6:00Speaker 01

  Which, you know, you have to watch YouTube. You have to be watching some.

• 6:04Ryan Holiday?

  You have to occupy the mind, otherwise you're, you're not. Yeah.

• 6:07Speaker 01

  I do that every day, seven days a week. My wife gives me a hard time because I never take days off.

• 6:11Ryan Holiday?

  Yeah.

• 6:12Speaker 01

  Even if we travel at like five in the morning, I get up at two.

• 6:15Ryan Holiday?

  Yes.

• 6:16Speaker 01

  Because my mind will be better if I work out.

• 6:18Ryan Holiday?

  I know. I didn't, I didn't get through this morning because I was staying in the same hotel as you and,

• 6:21Speaker 01

  Yeah.

• 6:22Ryan Holiday?

  And I had my kids and it is actually an interesting question. Maybe it goes to your risk book. What age can you leave children unoccupied in a hotel room?

• 6:29Speaker 01

  Yeah, that's a good question. Our oldest granddaughter is now just turned 11 and her sisters are eight and five, but I wouldn't leave them.

• 6:36Ryan Holiday?

  Yeah, I know.

• 6:37Speaker 01

  Unless I was like next door.

• 6:39Ryan Holiday?

  Yes, I know. I took my six year old to Las Vegas with me a couple of weeks ago. I had a talk. He was out of school and I can't perform unless I have worked out first.

• 6:49Speaker 01

  Right.

• 6:50Ryan Holiday?

  And so I was like, okay, you're gonna sit here. Here's your iPad. I'm gonna, I'm gonna do a very fast run on this treadmill. And I was like, it seemed normal to me. And then there was of course, no other children in like in the gym doing this. But I was like, I was trying to think, I was like, I, I think, I think I might be able to sit with it. But if my wife found out that I went for a run while I left them in the room, she would murder me. So.

• 7:13Speaker 01

  Yeah, no, same way. We've got the three granddaughters and we told the oldest will take her wherever she wants when she's turned 10.

• 7:20Ryan Holiday?

  Yeah.

• 7:21Speaker 01

  You know, we're thinking she's gonna want to go to Paris, you know, and she goes, Ohio.

• 7:27Speaker 01

  Really?

• 7:27Ryan Holiday?

  Ohio.

• 7:28Speaker 01

  Really?

• 7:29Ryan Holiday?

  Did you go?

• 7:30Speaker 01

  No, not yet. We're gonna take her as soon as she wants to go. It's.

• 7:34Ryan Holiday?

  Have a real fun trip to Cleveland, I guess.

• 7:36Speaker 01

  I was gonna say, what are you talking about?

• 7:38Ryan Holiday?

  Well, I, I loved the book and I thought maybe we start with character. You know, obviously we talk a lot about character, but you have a pretty good definition of it, which I don't know if I'd see like, character is one of those things you know, when you see it, but it is a hard thing to define.

• 7:54Speaker 01

  Yeah, it is.

• 7:56Ryan Holiday?

  What's your definition?

• 7:57Speaker 01

  Well, my definition is that it is a combination of equation, a product of two things. There is your deeply held convictions. And I've always got to explain that because it's not just little things you believe.

• 8:09Ryan Holiday?

  Yeah.

• 8:09Speaker 01

  It's things you've pressure tested.

• 8:11Ryan Holiday?

  Yes.

• 8:12Speaker 01

  Things you've thought about, things you're willing to live to or die for.

• 8:15Ryan Holiday?

  Yes.

• 8:16Speaker 01

  Times your personal discipline, which means if it's, if you have no discipline, the output is zero because we can all have these great convictions, but if we don't follow them. We don't have character.

• 8:29Ryan Holiday?

  Your ability or your willpower to bring them into existence that has to be added, layered on top of what you actually think. If you don't, if you don't stand for anything, you know, obviously you have no character, but you could be a very sort of philosophical and thoughtful person, but you need a certain fortitude to, to will them into existence.

• 8:50Speaker 01

  And that discipline, I widen that a bit because sometimes it's courage.

• 8:55Ryan Holiday?

  Yeah.

• 8:55Speaker 01

  You're under great pressure. Sometimes it's just the force of habit. You've got to force yourself to do those things that you believe. And most of us don't do that perfectly.

• 9:04Ryan Holiday?

  Yes, yes. Well, it is interesting because we tend to think of virtue or character as a thing that you have or a thing that you are. And I do think when you go back to the ancients, they were very clear that it was a thing that you did. Like Aristotle was saying that virtue is basically a habit. It's a practice. It's like any other skill. Like it, it seems weird to reduce something so moral down to a skill. But, but again, yeah, just thinking it doesn't mean anything. It's actually your ability and your, your track record of doing it that makes you the thing.

• 9:40Speaker 01

  And we can be both at the same time or both at different periods. I tell the story of Byron de la Beckwith in the book, who is a young marine in 1942, goes to Guadalcanal. Then he is badly wounded at Tarawa, is mustered out as an American hero.

• 9:56Ryan Holiday?

  Yeah.

• 9:57Speaker 01

  And part of the Tom Brokaw's greatest generation.

• 10:00Ryan Holiday?

  Yeah.

• 10:01Speaker 01

  20 years later, he murders Medgar Evers in his front yard.

• 10:04Ryan Holiday?

  Yeah.

• 10:05Speaker 01

  And so was he an American hero? Was he a psychopathic racist murderer?

• 10:11Ryan Holiday?

  Yeah.

• 10:11Speaker 01

  And the answer is yes.

• 10:13Ryan Holiday?

  Yes, yes. That, that actually is fascinating. I don't think it's something we talk about just how like the bravery, the people who went overseas to fight fascism and then came home and were the fascists is a, is a part of American history that we just kind of skip over.

• 10:30Speaker 01

  And do we have good days and bad days? And it gets to the, as the Greeks said, your virtue is what you do. And I think that's what your character is. So we do have days when my character is better than other days.

• 10:41Ryan Holiday?

  Mm hmm.

• 10:42Speaker 01

  And we have moments when I'm embarrassed by my character. And we have other times which I feel very good about it. And I think it's true of all of us. And I think it's true of our society too. We kind of rise sometimes and then other times we scrape the bottom.

• 10:57Ryan Holiday?

  Or maybe with someone like that, or some, some other people that we, we could point to now, where, so if the equation is your deeply held beliefs with your willpower and fortitude and commitment and all your, your actions. So what happens when you have someone who they have the fortitude, they have the, the courage, they have the strength, and then their compass gets spun around? Or then a less eloquent way to put it, what happens when their brain gets fucked up? Which happens, right? You know, people get sucked down rabbit holes. Like, this is why I think when we look at the four virtues, courage is important, discipline is important, justice is important, but then wisdom, the ability to separate a good cause from a bad cause, truth from fiction.

• 11:39Ryan Holiday?

  I think you sometimes see people who actually are high character, but they got spun around and now they think that this thing is a cause worth killing for, giving everything for, but they're just not on this planet anymore.

• 11:55Speaker 01

  That's right. Or sometimes they get on the bus and they kind of don't realize what they've done.

• 12:01Ryan Holiday?

  Yes.

• 12:01Speaker 01

  Suddenly they find themselves, oh my God, I am in a group or with people who are doing things that I fundamentally don't agree with.

• 12:08Ryan Holiday?

  Yes.

• 12:08Speaker 01

  But it's hard to back off once you're committed.

• 12:11Ryan Holiday?

  Yes.

• 12:23Ryan Holiday?

  Well, you, you talked in the book, this is something I related to. Like, I think when you look back on your life, however old you are, whatever you've gone through, you're going to wish you were more contemplative and sort of principle driven. Like, you look back and there, there's all these situations where you had your reasons, but I've found that the reasons don't age well. And, and it is kind of a shame that we leave the sort of reflective part to the end of life. We should be doing it as we go. I, I think about different decisions I made or people I worked for, things where I was in where I was just, as you said, just kind of going along with it or just too busy? And I wasn't going, does this align with who I want to be? Am I making the world better or worse? Is this right or wrong?

• 13:03Ryan Holiday?

  I was just doing and I wasn't thinking about, I wasn't thinking about it the way that I, I think I'm better at thinking about it now.

• 13:11Speaker 01

  Yeah, I feel the same way. I think of this story of Robert E. Lee. Of course, you preceded me at the military academy in my many years. More years than people want to say, but

• 13:21Ryan Holiday?

  Not that long.

• 13:22Speaker 01

  Yeah, he was known as the marble man as a cadet, and it wasn't a compliment.

• 13:26Ryan Holiday?

  Right.

• 13:26Speaker 01

  People meant that he was too stiff and he was too

• 13:29Ryan Holiday?

  Yeah.

• 13:30Speaker 01

  Interested in his future. And I go back to my time at West Point. I didn't think that way. I was there trying to wrench every bit of good time that I could out of a place that didn't want you to do that. And I almost lost it all

• 13:45Ryan Holiday?

  Yeah.

• 13:45Speaker 01

  because of my lack of personal discipline. And I could have been thrown out. It wouldn't be funny now if I was telling you I almost graduated from West Point. But you want life, you want to have a long-term view of life, but you don't want to be old before your time.

• 13:59Ryan Holiday?

  That's true.

• 14:00Speaker 01

  And there's that constant tension.

• 14:01Ryan Holiday?

  Yeah.

• 14:02Speaker 01

  How much of a very mature adult should you be when you're still young?

• 14:06Ryan Holiday?

  Yeah.

• 14:06Speaker 01

  But at the same time, don't make life tarnishing mistakes.

• 14:12Ryan Holiday?

  My experience with the service academies, I am blown away when you meet these 18, 19, 20-year-old kids and you're just like, I'm not, I wasn't like that at all. Like, there's a seriousness and a gravity and a dignity. And also, I would say, like, an earnestness that I think I was too insecure or fundamentally unserious to one if you've qualified for one of the academies, but just to be thinking about some of the weighty things that they're already thinking about at that age is very impressive.

• 14:43Speaker 01

  Which I agree. And I know your time at the Naval Academy is really valuable. And I think all the academies reflect that. And the challenge is always, I never wanted to see cadets who want to be admirals or generals

• 14:55Ryan Holiday?

  Sure.

• 14:55Speaker 01

  or think about that.

• 14:56Ryan Holiday?

  Yeah.

• 14:57Speaker 01

  You know, there are always a few in every class who are already thinking about it. Most of them want to be lieutenants or captains. They want to be good lieutenants or good captains.

• 15:05Ryan Holiday?

  Yeah.

• 15:05Speaker 01

  I think that's about the right focus. They want to be good sailors or good soldiers. If you're starting to think, I am going to be a great person someday.

• 15:14Ryan Holiday?

  Yeah.

• 15:14Speaker 01

  Then I think you lose focus.

• 15:17Ryan Holiday?

  Well, it's probably, that's probably the John Boyd thing about the to be or to do. Are you trying to go somewhere to accomplish and do a certain thing? Or are you after a certain title or rank? And you're kind of, you're forgetting that those things are extra. They should be rewards for doing the same. It's the same for, for a young person today that wants to be famous. No, you want to be so good at something that fame is perhaps a byproduct of what you're doing. But if the, if the aim is fame or money, you've got it backwards.

• 15:48Speaker 01

  Yeah, and I think if you are trying to be so careful, you never make any mistakes.

• 15:52Ryan Holiday?

  Yes.

• 15:53Speaker 01

  That you are unlikely to accomplish much either.

• 15:55Ryan Holiday?

  Yeah, you know, this idea that character is destiny, I come back to because character is fate. Because it's true, you know, you can sort of see in someone and it, either their, their, their fundamental greatness or their flaw. And then I don't know if I like the idea that we're fixed, you know, that, that we can't change. You seem to think that character is something that can evolve and grow and change, right? And it's something you can work on like any other skill?

• 16:24Speaker 01

  I think it has to.

• 16:25Ryan Holiday?

  Yeah.

• 16:25Speaker 01

  I don't think my view of my character when I was young was static. I had a sort of general heroic view of what my father was or what other heroes were. But as I went through life, a couple of things happened. One, life gets more complicated.

• 16:41Ryan Holiday?

  Yes.

• 16:42Speaker 01

  And those things you think, in this situation, I will do this or I will do that. And the reality is it gets gray, new pressures, new challenges. And so you think differently. And if we don't grow.

• 16:54Ryan Holiday?

  Yeah.

• 16:54Speaker 01

  Then I think shame on us.

• 16:56Ryan Holiday?

  Yes, if you're the same as you've always been, then you're saying that, you know, like, have you ever heard that? People go, if a 17 year old me could see me now, they'd kick my ass. And it's like, who cares what a 17 year old thinks? You know, like the idea that, that, that the smallness of your world then, that you're trying to get back to the purity of that is silly. Obviously, there's, I think, an idealism that you want to protect, that you shouldn't necessarily get more jaded and cynical as you get older. But your, yeah, your view and your understanding of things should certainly evolve.

• 17:26Speaker 01

  I remember an old quote by a Frenchman, his, he was told his son had become a communist. And he said, if my son had not become a communist by age 20, I'd have disowned him.

• 17:36Ryan Holiday?

  Yeah.

• 17:36Speaker 01

  If he's still a communist at 30, I will disown him.

• 17:39Ryan Holiday?

  Yes. Well, you know, there's that quote, like, if you're not liberal when you're young, you have no heart. If you're not conservative when you're older, you have no brain. I've always hated that quote, which, by the way, is a very old quote. But what I hate about that quote is, is sure, as you get older, you should get wiser. But the idea that you should become more risk averse, more closed off, that your heart should harden as you go. And here, we're talking about lower C conservatism, not any one specific political policy. But the idea that that you must become more conservative as you get older seems profoundly sad to me.

• 18:13Speaker 01

  Yeah, as you see more of society, I would like to believe that your empathy for people.

• 18:18Ryan Holiday?

  Yes.

• 18:18Speaker 01

  As you experience some of the difficulties other people do.

• 18:22Ryan Holiday?

  Yes.

• 18:23Speaker 01

  We had a fascinating ride in an Uber driver here today. And he had served in the army, starting back in 1988. And then he'd gone after four years, he'd gone into the Texas justice system. He'd worked in a couple of different prisons and jails. And he had a view of the world that's not exactly mine. But he had a view of the world that was pretty thoughtful for his journey.

• 18:44Ryan Holiday?

  Yeah.

• 18:45Speaker 01

  And so you have to respect that. You have to say, he grew with it. And now he's got grandkids. And he's thinking like I think it was very interesting.

• 18:54Ryan Holiday?

  Yeah, there is something about it's like exactly reverse, I think, that like the the older generation should be all about sort of keeping things as they are, because they're not going to be around. You know, if anything, you should become more empathetic, more concerned with the problems off in the distant future, because they're going to affect, you know, the people that you claim to care about the most. It's like, I love my grandchildren more than anything. By the way, I'm willing to bankrupt the country to make sure my benefits stay the same. You know what I mean? There's something backwards about how we're, we're doing it. Like, I gave this talk at this biohacking conference a couple of weeks ago. And there's this technology now where old people can get blood transfusions

• 19:35Ryan Holiday?

  from young people. The idea is like, the blood transfusion from a younger person in an older body reinvigorates the older body. But I said, to me, this is the perfect embodiment of our ass backwards system, where the old are sucking the blood from the young. Instead of planting trees in whose shade they'll never sit, you know? But yeah, I think if you get more cynical as you get older, that's very sad.

• 20:00Speaker 01

  Well, it is. I mean, there was a movie that I watched a few years ago about raising orphaned children and then harvesting different organs from them.

• 20:09Ryan Holiday?

  Again, a metaphor.

• 20:11Speaker 01

  I go, oh, my word. I mean, what are we thinking about here?

• 20:13Ryan Holiday?

  But we do a version of that. So, character can't be fixed. I think we have to believe that because otherwise, what are we doing? And then I think we have to understand that philosophy wasn't supposed to be riddles and abstractions, but the medium through which society developed its character. And by the way, this is also what the study of history was, and this is what literature was. It was all focused on what the ancients thought was the most important thing, which was the development of character in the next generation. And now, you know, who knows what the philosophy professors are doing at insert university? And you read most literature and you're like, what is this?

• 20:58Ryan Holiday?

  You know, like, I don't really, it's all the anti-heroes and there's something interesting. Even history seems to be so bogged down in facts and figures and not what can we learn from this about the good life and a good world?

• 21:14Speaker 01

  Think we've made knowledge of history and philosophy as something pretentious.

• 21:18Ryan Holiday?

  Yes.

• 21:19Speaker 01

  And I remember I went to the Navy War College when I was a mid-grade officer and the lecturer got up, we were reading the Iliad as part of the course. And he says, well, if you haven't read it in the ancient Greek, it's just not the same. And, you know, most of us just kind of rolled our eyes and said, we're lucky you're getting us to read this at all, cut down version. But I think when we make philosophy not approachable for the average person, and when somebody throws around the terms in a way that that highlights their erudition and not yours, we push people away from it, when in reality, it should be eminently practical.

• 21:57Ryan Holiday?

  Yes.

• 21:58Speaker 01

  That's what they were actually trying to do. This is the world you live in, and here's a way to think about it.

• 22:03Ryan Holiday?

  Yeah, and these weren't like these sort of tenured academics. I mean, Socrates fights in the Peloponnesian War, like a great power conflict. And, and, you know, they ran for office, they played sports, they were not like eggheads. They were of the world and they were trying to figure out how to have a good life in a bad world. I've been thinking about this recently, how, how we tend to romanticize the past. And again, you know, Athens looks cool in the ruins and it looks cool in the pictures, but Socrates is living through Sparta and Athens and existential conflict. And then he lives through the 30 tyrants and then he lives through, you know, a death sentence. He doesn't live through it, but it concludes with a death sentence. You know,

• 22:47Ryan Holiday?

  the Stoics lived through Nero, the fall of the Republic, Marx realist's emperor during a plague and a famine and a flood. It, it was just as scary as now. And they weren't just walking around in their togas, eating olives and figs and stuff. It was stressful and they, they thought, just like we do, that things were falling apart or things were moving too fast. And, and philosophy was supposed to help them deal with the, the practical problems of that existence.

• 23:16Speaker 01

  And I think of the founding fathers. We tend to say now, they were 10 feet tall. What would they do? They were deeply flawed and they realized that their fellow citizens were deeply flawed as well.

• 23:26Ryan Holiday?

  Yes.

• 23:26Speaker 01

  And so they set up a system to account for that.

• 23:29Ryan Holiday?

  Yes.

• 23:30Speaker 01

  And I think sometimes we shouldn't be intimidated by that. We should say, we are not founding fathers now.

• 23:36Ryan Holiday?

  Yeah.

• 23:37Speaker 01

  But there has to be a term because we now own where the nation is and we're responsible.

• 23:43Ryan Holiday?

  Well, they were, I was just working on this for a talk I'm going to give next week. They were, the average age is like 40, some were 20, but they were older than their years in the sense that they were steeped in these classical ideas. Washington is the only one who doesn't read the classical texts in Greek or Latin, but he did read them in English. And like, I've been joking about this because Ron Chernow was here a couple of weeks ago. The Hamilton of its day was this plague. Called Cato, that was all about classical virtue and discipline and courage and principle and country. And they all knew it by heart. They were sort of steeped in these ideas. I think,

• 24:24Ryan Holiday?

  again, yeah, we tend like when I learned about the founders, they talked about Locke and like these other, they talked about their, their sort of legal philosophical influences, which to me is secondary to the philosophical, the classical philosophy that influenced them as human beings, like, like Adams's line about how a country without virtue and the people will break through the constitution like a whale through a net. They understood that they were setting up this legal system, but it was still incumbent on the individual to be a man or woman of character, that you have to cultivate this. And that, that's the primary purpose of education was to cultivate character in people.

• 25:06Speaker 01

  I think that's an extraordinarily important point that I happen to feel that we don't do very well right now, because we don't have a body of, now, they were elites, let's be honest, not every person, but we don't have a body of knowledge that is sort of entry level requirement for being in the conversation. And because of that, we don't have a foundation where we can talk about things and refer to things through those ideas. And I think that's a mistake.

• 25:34Ryan Holiday?

  Yeah, when they were signing the Federalist Papers with these pseudonyms, everyone understood which ancient figure they were alluding to when they called someone a Catalin or a Cato, were they a Republican or a usurper? There was just this, this sort of shared understanding of the good guys and bad guys, cautionary tales, exemplary examples. When, when, when Washington leaves after two terms, and when he resigned his commission before that, everyone understood it was, this was a nod to Cincinnatus. And today, I mean, how many people could even know that Cincinnati is from Cincinnatus, right? But this is a myth that probably isn't true. Like, there probably was no Cincinnatus, or maybe it didn't happen

• 26:19Ryan Holiday?

  that way. But that's secondary to the fact that for thousands of years, people were taught about the story of Cincinnatus as a model of someone who, who temporarily held power on behalf of the people and then was Willing and disciplined enough to lay it down.

• 26:38Speaker 01

  You know, you've just ruined my day if Cincinnatus wasn't real.

• 26:41Ryan Holiday?

  Yeah, I don't think you, I mean, there's no verifiable proof he existed.

• 26:44Speaker 01

  Yeah.

• 26:45Ryan Holiday?

  But I feel like history nerds out about like, did Washington actually cut down a cherry tree or not? It doesn't matter. That's not the point of the story.

• 26:54Speaker 01

  You know, there was a book when I was a younger army officer, it's still around, written in 1968 by Anton Meyer called Once an Eagle. And it was read by most of the army officers of my generation.

• 27:05Ryan Holiday?

  Yeah.

• 27:06Speaker 01

  And it's because of that, it became something that you could refer to.

• 27:11Ryan Holiday?

  Yes.

• 27:11Speaker 01

  Nowadays, we use lines from The Godfather, but from this book, there were these two characters, Sam Damon and Courtney Massengill. One was really a good guy and one was not a good guy. But I read the book about seven times through my career. And when I was very young, it was binary. Sam Damon, Nebraska farm boy, enters the military as an enlisted man, wins a medal of honor, and he's thrifty, brave, clean, reverent. And Courtney Massengill's an Ivy League conniver. But as you read it, as you get older and you are in a more complicated part of your career, you start to view the characters differently.

• 27:46Ryan Holiday?

  Yeah.

• 27:46Speaker 01

  You don't like Courtney Massengill, but you start to get it.

• 27:50Ryan Holiday?

  Yes.

• 27:51Speaker 01

  And you don't, you still love Sam Damon, but you see his limitations.

• 27:55Ryan Holiday?

  Yes.

• 27:55Speaker 01

  But the most important thing is in the military, someone could refer to someone else and they say, he's a Courtney Massengill. And you immediately go, I got it.

• 28:04Ryan Holiday?

  Yeah.

• 28:05Speaker 01

  Yeah. And the same for Sam Damon. So I think having those common things we can analogize to are really important.

• 28:24Ryan Holiday?

  Well, just to have a text and evolve with it is a very powerful thing. I was going to write something about Gatsby. It's the 100 year anniversary of Gatsby this year. And that's a book, you know, I read in high school and you realize, oh, they're teaching it so you know what the Jazz Age was, not as what it's supposed to be, this sort of, these different personalities, this, the effect of money on. People, one of the scenes that I just reread it and one of the scenes that strikes me the most is there's this part where Gatsby wants to get to Nick Carraway's cousin, who he's obviously in love with, and he says, hey, you know, I had this like little business thing. Would you want to be involved in it? And he goes, no, I'm okay. Nick Carraway

• 29:05Ryan Holiday?

  does. And he says, you know, later, I reflected that on that as potentially being one of the great crises of my life, that he realized that Gatsby was trying to draw him into the criminal underworld. And he had just sort of shrugged it off. And he didn't realize just how narrowly the whole course of his life might have turned out very differently. And, you know, you're gonna miss that at 16. I missed it ironically in my 20s, when I desperately needed to see that, when I was in my own potentially going down a road like that. And then, you know, here in my late 30s, I go, oh, that's what this is. And there's something about coming to a book over and over and over again, that you're able to, once you get the basic facts, then you notice all these other layers that you didn't know were there.

• 29:50Speaker 01

  Absolutely. It's like looking at the Spartans in the military, particularly after nine 11, we fell into another phase where we just were in love with the Spartans.

• 29:59Ryan Holiday?

  Yes.

• 30:00Speaker 01

  But they were an awful lot like the pre-Civil War South.

• 30:04Ryan Holiday?

  Yes.

• 30:05Speaker 01

  And they did things to the helots or the slave population that were unthinkable.

• 30:10Ryan Holiday?

  Yes.

• 30:11Speaker 01

  And they did it routinely.

• 30:12Ryan Holiday?

  Yeah, fetishizing a military death cult.

• 30:15Speaker 01

  Well, that's right. And, you know, they did some heroic things, but you look just two dimensionally at anything or anyone.

• 30:23Ryan Holiday?

  Yes.

• 30:24Speaker 01

  And you draw away a certain view. And I think that's dangerous.

• 30:27Ryan Holiday?

  Yeah, the Stoics talk about how we never step in the same river twice. And so when you come back to these books, particularly like, there's the experience of rereading a book you've already read, and you see what you noted. And then, like, just reading Gatsby again, there's this annotated 100 year anniversary edition. So I'm reading it a fresh copy, and I'm noticing different things because I'm not even able to see what I remembered before. It was actually funny. I wrote this book a couple of years About Peter Thiel and this crazy thing he did. And I had been reading one of Eisenhower's memoirs at the same time. And then I remembered that Mayor Wolfsheim, the character in Great Gatsby is the stand in

• 31:08Ryan Holiday?

  for the gangster Arnold Rothstein, who fixes the 1919 World Series. And did you know this?

• 31:14Speaker 01

  No.

• 31:15Ryan Holiday?

  Okay, so did you know the 1919 World Series was fixed?

• 31:18Speaker 01

  I probably know more about that than I knew about Gatsby.

• 31:21Ryan Holiday?

  So there's a character in Gatsby that's supposed to be that. And I was reading in Eisenhower's memoirs, he was listening to the radio when the news broke that it had been fixed. And he's talking about how that always stayed with him, that events, he'd remembered watching it on the, I guess probably listening to it or whatever. And then later it breaks that it had been fixed. He goes, things are not always what they seem. There's always things beneath the table. And this always, this shaped his understanding of power and news, et cetera. So I go back and I'm gonna, as I'm writing a book about a conspiracy, I'm like, I'm gonna go read that section in Gatsby. And in that section in Gatsby, Nick Caraway is introduced by Gatsby to Mayor Wolfsheim, who is Arnold Rothstein. And Gatsby goes, this is, you know, Mayor Wolfsheim, he fixed the 1919 World Series.

• 32:06Ryan Holiday?

  And Caraway goes, you know, I knew that it was fixed, but the idea that it had been a person who had done it, that one person had affected the lives of millions of people. He's like, I just thought, I thought it happened as, like he says, like the result of an inevitable chain, not that an individual could change the course of history. And so anyways, like, of course, I missed that the first five times I read the book, but it's not until I'm writing about something and then reading something else, and then you suddenly make these connections. And so it's not enough to just read some of these texts, the Odyssey, whatever, once. You have to have this kind of lifelong engagement with it, which I'm sure was easier in the ancient world when there are a lot fewer books.

• 32:48Speaker 01

  But I wish we had a culture where we talked about books more because I can read a book and I probably get 40% of the real message. But if I'm in a group with somebody who then describes, like Gatsby, I read Gatsby back in school, but you just told me some things I had no idea.

• 33:04Ryan Holiday?

  Yeah.

• 33:05Speaker 01

  But if I'd been in a group where somebody said, oh, yeah, this.

• 33:07Ryan Holiday?

  Yes.

• 33:08Speaker 01

  I wouldn't have probably admitted it to the group.

• 33:10Ryan Holiday?

  Sure.

• 33:10Speaker 01

  But I would've said, oh, for sure. But trying to get as much as you can out of something as complicated as a good book.

• 33:18Ryan Holiday?

  Yes.

• 33:18Speaker 01

  Is important.

• 33:19Ryan Holiday?

  Yes, and sometimes you just can't know what you didn't know until you know it. I mean, obviously, I've had this 20 year relationship, I guess it would have been 15 year relationship with Marcus Schurles' meditation since I read in college. And then it's not until we're in the middle of the pandemic that I go, oh, wait, he wrote this during a plague. This is a plague book and he's not being metaphorical here. He's being literal. He's literally talking about the way that this screws with our minds when there's this thing out in the air killing people and the, the stress and strain it puts on society and relationships and how exhausted we get. And, and you go, oh, unless I'd been alive in 1919 and experienced that pandemic, I couldn't have ever gotten this until we're here.

• 34:04Ryan Holiday?

  And so I think that's that it's critical that you not just read, but then you go out and experience because that informs the reading and it's, it's this sort of endless feedback loop of reading, experiencing, reading, experiencing.

• 34:18Speaker 01

  Absolutely.

• 34:19Ryan Holiday?

  You talked about something, you said like, what is it like the tale of the dinosaur?

• 34:23Speaker 01

  The dinosaur's tale, right?

• 34:24Ryan Holiday?

  Yes, what is that?

• 34:25Speaker 01

  Yeah, um, and I used a story, a real one, uh, where I was commanding a battalion of Rangers and we were told that the chief of staff of the army was visiting, which is the head of the army, really important person coming out.

• 34:37Ryan Holiday?

  Yeah.

• 34:37Speaker 01

  And because his, we do a preparation for a big demonstration and we're going to really wow him. We didn't want to do it, but once you're prepared, you want to go on and show him what you got. It's a Friday afternoon and about noon, we get this call that says, well, the chief's schedule got too busy. We canceled the afternoon, so we canceled this. And so had to go to the troops and tell them, all right, you've done all this stuff. You've rehearsed, we were all ready. It's canceled, he had something more important. And everybody was disappointed.

• 35:08Ryan Holiday?

  Yeah.

• 35:09Speaker 01

  Now, if you'd canceled it on Monday, they'd have said, great, we avoided it.

• 35:11Ryan Holiday?

  Yeah.

• 35:12Speaker 01

  But after you've done all the work. And what it really came down to is you get very senior, very important, you've got handlers around you. And if you're the senior person and the schedule starts to get full, I go, we got a problem here, Ryan, we gotta, we gotta cut some stuff. And you go, is that any problem?

• 35:32Ryan Holiday?

  Not a problem for you.

• 35:34Speaker 01

  You know, I go, no, sir, no problem.

• 35:36Ryan Holiday?

  Yeah.

• 35:37Speaker 01

  And you are like a dinosaur where you've gotten huge, your tail's big, your brain didn't get any bigger, and you turned and your tail knocked stuff over. And it happens all the time. And unintentionally, the, the decisions or non-decisions of very important people affect incredible numbers of people. And it's, it's still your fault. If you're the senior person, even if the schedule got full, there wasn't another option, it is your fault.

• 36:06Ryan Holiday?

  Yeah.

• 36:07Speaker 01

  Now, that means that whenever possible, you should be informed of it. You should ask probing questions. Now, wait a minute, what do we cancel? And what's the effect on people and that sort of thing? And understand that you're doing damage that you probably need to repair.

• 36:22Ryan Holiday?

  And you, and, and no one's ever going to come to your face and go, sir, that was rude, or sir, so and so missed his daughter's recital for no reason as a result of what you did. So you, you're first off, not aware of the impact you're having on people. You're not even, you're also not aware of the emotions or the, the resentments that it's generating. And there's going to be consequences for that at some point, too, I'm sure.

• 36:43Speaker 01

  Some are huge. Just like being late to a meeting.

• 36:45Ryan Holiday?

  Yes.

• 36:46Speaker 01

  It's a sign of power on the part of some people. They automatically show up late. So everybody is convened and waiting. And then they breeze in and they go, sorry, I'm late.

• 36:55Ryan Holiday?

  Yeah.

• 36:56Speaker 01

  They didn't have to be late. I mean, occasionally, things are going to happen. But the reality is, it's a sign of arrogance.

• 37:02Ryan Holiday?

  Yeah.

• 37:02Speaker 01

  And it builds up this scar tissue. It builds up resentment over time. And leaders need to understand they're doing that.

• 37:09Ryan Holiday?

  Yeah. There's a story about Antoninus, who's Mark's realist's successor. And the, obviously, the Roman Empire is enormous. And they would have to tour the different provinces. They'd go see this people, they'd inspect the troops over here. And it's also, I'm sure, a very pleasurable endeavor for the emperor. He's feted at parties and they're bringing him the best this and the best that. And, um, but Antoninus does almost none of this. And we're told that he doesn't do it because he understands how expensive and how exhausting it is to host the emperor. And I just think of the empathy to go like, hey, I would like to do this, but I wouldn't like to do it for the outlay that it has on other people. It's not worth it.

• 37:53Ryan Holiday?

  And I think sometimes as a leader or as a person who's used to getting what you want, you just think about whether it's good for you and you're not thinking about the, what it means for it to be good for you, what it takes out of other people for you to get what you so willingly accept or appreciate.

• 38:10Speaker 01

  When I was a, uh, still on active duty, there was a brigadier general in the army who was in recruiting command. And so he would go around the United States to visit recruiting locations. And his aide de camp wrote a letter that was sent out to all the different subordinate units so they could always be prepared for his visits.

• 38:28Ryan Holiday?

  Yeah.

• 38:28Speaker 01

  And of course, it ended up going viral because I remember something. It says that the general is a big man, so you need to get a minivan and take out the rocket seats so he's got room. And then it said, he wants a diet Coke or diet Pepsi in there in a bottle, not a can. And then it goes can taste funny. And then it says, I remember this line, if there are chocolate chip cookies, they will be consumed. And I remember seeing this thing and I meant, oh my God. One, who's going to provide the chocolate chip cookies? Who's paying for that? It's not the army.

• 39:03Ryan Holiday?

  Sure.

• 39:04Speaker 01

  And if the general knew about it, hopefully he went ballistic.

• 39:10Ryan Holiday?

  Right, he might not, he might have one time said, "I like chocolate chip cookies."

• 39:13Speaker 01

  Right.

• 39:14Ryan Holiday?

  And he doesn't know that down the line, this has come down as the word of God.

• 39:18Speaker 01

  But this happens.

• 39:19Ryan Holiday?

  Yes.

• 39:20Speaker 01

  And whose reputation was really impacted was not this aide, this overeager aide. It's the person themselves.

• 39:28Ryan Holiday?

  Well, it's not even them. It's also just, this is now the frustration with leadership generally, or the public and what you're a representative of.

• 39:36Speaker 01

  Exactly.

• 39:37Ryan Holiday?

  There's a story about Cato. So, Cato's a Roman senator, well-known, later a general. He's traveling, I think, maybe for personal reasons, he's traveling through the empire. And he would often travel ahead of his baggage train. And, you know, he gets to the city one day, and usually, you know, they know he's coming. And so, there's this, the whole rigmarole. And he gets there and no one's there to greet him. And he's, he just sits, he sits down and waits for the people to arrive. And then, when they get there, "Oh, my gosh, we're so sorry," it's a whole thing. And he says, you know, "I don't care." He's like, "You should just, you should just be aware that not all your guests will be Catos." And, and the point is, you want to be chill. And on the other hand, you want to understand that everyone's not always going to be so understanding.

• 40:22Ryan Holiday?

  The reason Kobe Bryant played for the Lakers and not the Nets is that as he was touring the different teams before he gets drafted, the Nets had to send him back to LA or something. He visited the Nets, they booked his travel. They put him on a middle seat in economy on the way home. And he was like, "No, never these." So, you never know, like, you want to assume everyone's chill and humble about these things. And they're not going to be. I think about the contrast of those two stories.

• 40:48Speaker 01

  You know, that's fascinating. And you, you hope you're not the kind of person who needs or demands that.

• 40:54Ryan Holiday?

  Yeah.

• 40:54Speaker 01

  I kind of think we have gone too far in our country towards a regal treatment.

• 41:02Ryan Holiday?

  Sure.

• 41:02Speaker 01

  Of the president.

• 41:03Ryan Holiday?

  Yep.

• 41:04Speaker 01

  You know, I actually think we ought to get rid of hail to the chief. I think that was not the idea when we formed the country, that we were gonna... I don't think we need over-the-top accommodations or airplanes and, and things like that. And... Because I think it actually sends a bad message internally and externally when we go too far with that. And that's true of some corporate CEOs and other leaders as well.

• 41:29Ryan Holiday?

  There's something about the British system where the, there's a separation between the embodiment of the state and then the actual person running. I don't think they did it on purpose, but that's probably healthier, right? Because the person doing the job is wearing the suit and is, is, you know, much more a government employee and the other person is the symbol. And in, in the US uniquely, those things are merged. Actually, that's a problem. That's a, that it's like, no, the pomp and circumstance should be in the legislative body, which is the representative of the people. And then the executive is the executor of that thing. We've got it. We have a misperception of what the president's job is and who they are,

• 42:13Ryan Holiday?

  what they are supposed to represent. I think that's the problem.

• 42:16Speaker 01

  I've never thought of it that way, but I really like that. You know, I got to go into number 10 Downing Street.

• 42:21Ryan Holiday?

  Yeah.

• 42:21Speaker 01

  And it's very modest in there.

• 42:23Ryan Holiday?

  Yeah.

• 42:23Speaker 01

  It's, it's not very nice. And where the prime minister works and lives is, is pretty limited, but it, but it does. It keeps a real realism.

• 42:32Ryan Holiday?

  Yeah.

• 42:32Speaker 01

  What am I doing here?

• 42:33Ryan Holiday?

  Yes. Yeah, yeah. It's also weird. Like, the vice president travels or goes around to do the, is sort of the president's emissary and the ceremonies or whatever. But there is something about, yeah, you're, you're puffing this person up in a way that is probably not, not healthy. But you do need that. Who, who greets the team when they wins, win the Super Bowl? Who pins the medals on people? You do, that is part of the role of a state. But it's hard for, you don't make the CEO of a company do a lot of those things.

• 43:04Speaker 01

  Why don't we create a separate thing?

• 43:06Ryan Holiday?

  Yeah.

• 43:06Speaker 01

  Not royalty, but elect somebody with those skills and that interest.

• 43:11Ryan Holiday?

  Yes.

• 43:11Speaker 01

  And they could be that. And we could give them a 10 year term so that they don't have to change too much.

• 43:17Ryan Holiday?

  But that goes to your point about the founding fathers, which is, I think we have, as smart as they are and as impressive as the system they created is, we have, we have lost the ability to

• 43:30Ryan Holiday?

  Tweak or improve the system. You know, I mean, the idea of amending the Constitution is effectively inconceivable, you know, and if not impossible. It's probably impossible because it's inconceivable. But they were tweaking it, I mean, not that long ago. The last constitutional amendment is not some lofty thing. It's like that Congress can't give themselves a pay raise.

• 43:53Speaker 01

  Yeah, and if you think about it, it was designed to be updated.

• 43:56Ryan Holiday?

  Yes.

• 43:56Speaker 01

  It was the whole idea of-

• 43:58Ryan Holiday?

  They updated it right after they wrote it the first time.

• 44:00Speaker 01

  Exactly.

• 44:00Ryan Holiday?

  Immediately after, they were like, we missed all the important stuff.

• 44:03Speaker 01

  And we also think that the founding fathers, what their intent was, is sacrosanct.

• 44:09Ryan Holiday?

  Yes.

• 44:09Speaker 01

  Well, it is what their intent was back 250 years ago.

• 44:12Ryan Holiday?

  Sure.

• 44:13Speaker 01

  Their intent might be different now.

• 44:14Ryan Holiday?

  Yeah, they don't, they didn't know some stuff. I mean, people do that with the Stoics, too. It's like, it was 2,000 years ago. They didn't know about a lot of things. Like, I would be disappointed if they were not on the same page as us about a lot of stuff that we have subsequently discovered and learned. That would be, that would be the whole point of it. So, is you just become closed off to new ideas once you get to a certain age? That's a shame.

• 44:38Speaker 01

  I'm 70, yeah, that's what you do. You can't do that because just too much comes, and it's too interesting.

• 44:48Ryan Holiday?

  Thanks so much for listening. If you could rate this podcast and leave a review on iTunes, that would mean so much to us, and it would really help the show. We appreciate it, and I'll see you next episode.