


In this episode of The Daily Stoic, host Ryan Holiday explores the significance of character in contemporary society. He discusses the evolution of character over time, referencing historical examples and the insights of General Stanley McChrystal, who emphasizes the importance of integrity and personal growth through adversity.
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1:05Welcome to the weekend edition of the Daily Stoic podcast. On Sundays, we take a deeper dive into these ancient topics with excerpts from the Stoic texts, audiobooks that we like here or recommend here at Daily Stoic, and other long form wisdom that you can chew on on this relaxing weekend. We hope this helps shape your understanding of this philosophy, and most importantly, that you're able to apply it to your actual life. Thank you for listening.
1:43This isn't a solo journey. Although there is something singular about the great minds and artists of history, it's interesting that most of them were not lone wolves or recluses. In fact, when you study most exceptional and wise people, you find that they were often part of a scene, a community, a collective, a culture, a movement full of other artists or writers or entrepreneurs or philosophers. Think of the Scipionic Circle, a group of Roman politicians and philosophers who met at the House of Scipio, one of Rome's greatest generals, to discuss philosophy, share ideas, and explore stoicism. Think of the Transcendentalists, a movement which Emerson started in Concord in 1836, or the Lost Generation who came of age together in Paris after World War I.
2:31Think of the Bloomsbury Group in 20th century London, or the PayPal Mafia in Silicon Valley, or the grunge scene in Seattle. These people might have done their work alone, but they developed their ideas, their point of view with people. Obviously, they did it with the right people, too. As Seneca said, we must associate with those who are likely to improve us and welcome those who we are capable of improving. It's pretty rare that someone doesn't become better by surrounding themselves with great people, socially, professionally, spiritually. And it's also pretty common that a potentially great person can be ruined by not-so-great influences.
3:12That was Epictetus' observation. If you live with a lame man, you will start to limp. It is key, then, in the pursuit of wisdom and the good life that we cultivate the right influences, the right scene, the right partners, teachers, and friends. Conversely, we must steer clear of the wrong ones or we can end up foolish or worse. That's actually one of the key ideas in the new book, Wisdom Takes Work, which you can pre-order now. We've been talking about it. There's just a couple weeks left, and it would mean a lot if you did. That's at dailystoic.com slash wisdom. The idea is that wisdom, like success, isn't a solo journey.
3:49It requires community and discourse and the friction that comes with engaging with other minds. So we must find or make a scene that inspires and challenges and understands us. We must find a community that holds us accountable and pushes us to go beyond our limits. And if you want to get a little scene going with me, we're going to be having dinner here in Bastrop, Texas around the ideas in the book. We've been doing it for all the books in the Virtue series. We had one for courage. We had one for discipline. We had one for justice. And this will be the fourth and final Philosopher's Dinner. We're going to have it inside the painted porch.
4:26And it's going to be a small gathering, just a handful of us. We're going to sit down and talk about virtue and philosophy as they did 2 ,000 years ago in the Scipionic Circle. You know, usually when I get to meet my readers, it's like I'm doing a big talk. I'm on stage. They're down there. This is just going to be us having dinner. We have it catered by my favorite place here in Bastrop Storehouse. And it's going to be awesome. And all you have to do is buy 120 copies of Wisdom Takes Work and then come see me in Bastrop, Texas. I'll send all the details, but you can grab that at the landing page, dailystoic.com slash preorder.
5:00There's a bunch of bonuses in there. I think it'll be great. I'm looking forward to meeting you. Usually we don't do these meditations on Sunday, but I thought it was worth doing. I'm looking forward to meeting all of you at the Painted Porch. See you soon.
5:19Hey, it's Ryan. Welcome to another episode of the Daily Stoic Podcast. I hope you are all doing well. I did this email a couple of weeks back for the reading list email. And basically the premise was that we are not the first people to live in a time that feels like the world is falling apart. We're not the first people to live through political dysfunction or cruelty or technological disruption. We can quite easily forget that Socrates lived through the great power conflict and the 30 tyrants. The ancient Stoics lived in the time of Nero, and Cato lived in what Cicero called the dregs of Romulus.
6:01Mark Cybillus was there for the decline and fall of the empire. Seneca literally watched Rome burn. My point is that people have always lived through difficult times, and those difficult times tend to repeat themselves. So what do we need to equip ourselves with? What can we learn from those people in the past to equip us for this moment? I would say we should read history, we should read psychology, we should read biographies, we should read information that has a long half-life stuff born of hard-won experience. And one of the books I recommended at the end of that list was this book, which I think was one of the best books I read in the last year or so.
6:40It's On Character by General Stanley McChrystal, and the subtitle is Choices That Define a Life. The Stoics feature in and out of the book because the Stoics believed that character was destiny, that really what your values were determined what kind of person you were and how you would handle the ups and downs of life. And I felt like this was kind of a throwback to an older style of books. It's basically a meditation on like a singular theme, a bunch of short essays and stories. It's very earnest and I thought vulnerable. General McChrystal, since he left the army, you know, has done his share of consulting and advising.
7:22He's built a big company. He's worked with a lot of interesting organizations. If what he was after was more speaking gigs or consulting opportunities, he wouldn't have written this book. It felt to me like the thoughts of a man at the later stages of his career in life, reflecting on what he's learned, the mistakes he's made, the future he hopes to leave his children and grandchildren. And I just love the book. And I've been raving about it. We had him on the podcast. I thought it was a great interview. And as he was leaving, I said, hey, could I run a chapter from the book on the podcast? And he was nice enough to say yes.
7:57And so was his publisher. So thanks to Penguin Random House for allowing this. This chapter is titled, Does Character Still Matter? I think it does. I think it must. I don't want to live in a world where it does not matter. If you don't know who General McChrystal is, he's a retired U.S. Army general, best known for his command of the Joint Special Operations Command in the mid-2000s. And then he established a consultancy firm called the McChrystal Group. He had some ups and downs as part of that career. Maybe you only heard about him in the news when there was a controversial Rolling Stone article, and then he ended up resigning.
8:32I'm sure he would concede that he made mistakes there, that he wished it had gone differently. He didn't really control that it happened. But I do think his character shined through in the years since. He's not become this sort of embittered, radicalized, angry person. This is something we talked about in the episode. Actually, let me play you that little chunk here because I asked him about this specifically.
8:58I've always thought it's interesting about you because we live in this, I guess today we sometimes call it cancel culture. We have these figures where something happened to them, they got fired, they screwed up, there was a scandal, whatever. It's this breaking point in their public persona, their life, where the resulting person is bitter or angry or aggrieved or becomes a reactionary or switches political parties, just sends them on this trajectory that they wouldn't have been on otherwise. and I find it very impressive and we don't need to get into the specifics of it for you but I am curious about how you handled that closing of your career one of the things that Stoics talk about is they say it can only harm you if it harms your character that basically you can lose the job you can lose your career you can lose all your money all these things can happen to you but the harm is if it turns you into something that you're not and I feel like And you just went in a different direction than so many people in that position.
10:05Yeah, thanks for bringing it up. I in no way compare myself to James Stockdale. Yes. But if I think about his experience where he lost control over everything about his physical well-being and in short term, almost everything, he chose not to let that re-identify him, change who he was. Yes. In fact, I would argue it strengthened and it expanded him. And I think I was lucky enough when I resigned from the military after 34 plus years, and I suddenly had my previous identity challenged, had a couple of options. I could become an embittered former general, and you'd have me on your show to tell that story about how I got screwed.
10:50You could be in Steve Bannon's war room right now. Yeah, exactly. And instead made the decision with the help of my wife, Annie, not to do that. Yeah. instead to say, okay, I am not a bad person. And so I'm going to be as good a person as I could be going forward. And that became really liberating. And the thing that was important to remember is you don't do away with the injury. You can't pretend it didn't happen. It did happen. And to the degree I was agent of it, I have responsibility and I don't dodge that. But on the other hand, if I say there is redemption, I can move forward. I can be as much as I'm capable of being going forward.
11:32That's what I'll do. And that's been the luckiest point in my life because I never to that point in my life, I've had pretty much unbroken success. There's some hard things, but, you know, generally. And if I think about it, I came out of those years of war. I had lost no limbs. I wasn't killed. I wasn't, you know, in other ways damaged. So I don't have much to complain about. Right. And then I have opportunities and I have the opportunity to be whatever I will myself to be. Yeah. And that's the direction I've taken. And, you know, it's limited by my talents and whatnot, but I'm so happy I did that.
12:14So we had a great conversation. listen to the whole episode but here is a chapter on character and whether it still matters you can grab on character at the painted porch you can check out his other books which he signed copies of team of teams and leaders one of my favorite writers one of my favorite thinkers and i hope you enjoy this episode of the daily stoke podcast
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14:31And this truck wasn't just transportation getting me to and from my house. It unlocked a whole different style of living for us, not just on the ranch, but in our little Texas towns. There were places I could go now that I couldn't go before, especially out here in the piney forests, through the fields, and on the unpaved roads like the one that I lived in. We got to go deep into the hill country's wild beauty. We've driven all the way out to East Texas. We've driven it across the country. And by we, I mean not just my wife, but both my kids who I drove home from the hospital in that truck. Toyota trucks are built for those who understand that the best adventures happen when you're willing to veer off course.
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15:48Does character still matter? Character is more essential than ever to our world. I've spent a lifetime studying leaders, heroes, and scoundrels, with more than a few individuals who are justly categorized in all three groups. We seek to define each person's character so that we can venerate or denounce them, but in most cases, cleanly defining who a person is proves elusive. Many of us struggle to know what even our own character is. This raises the obvious question of whether character is real or a useful construct to advocate for selected values and behaviors. Many of us profess faith in things we can never confirm, like miracles, but we accept them anyway.
16:42Could character be the same? Might what we venerate, the bedrock of values supporting a superstructure of worthy behaviors, be nothing more than an ideal? Is it dead, dormant, or simply difficult? I was blessed to have loving parents of admirable character, mostly good sports coaches, and later some excellent military commanders. I was exposed to decades of values-oriented education and training. Raised in an era when even my elementary school unabashedly advocated for patriotism and ethics, then molded at West Point through a narrative of service, discipline, and an unequivocal honor code, I wouldn't have been able to dodge thinking about character.
17:34Then there was the real world. We're all unsurprised when people we don't respect validate our estimation of them by being dishonest, disloyal, or selfish. It's strangely satisfying to be both right and feel morally superior at the same time. We're also disappointed when leaders we esteem prove all too human, and friends, family, and teammates fail to live up to the standards we've hoped for. We make excuses for those we love, but when they deviate from what we expect, it hollows out our faith in their character. Hardest of all is when we see this lack in ourselves. No doubt there are people who celebrate their ability to circumvent or undercut laws and norms, but most of us hope not to be that way.
18:30Still, in moments testing our integrity, compassion, and commitment to things we've embraced, most of us remember when we were not the person we'd hoped to be, when our ambition, ego, impatience, and greed led us to act in ways we might describe as out of character. But maybe the question is whether this is just our real character revealed. Nothing hurts quite so much as admitting we're not the person we claim to be. If we watch people of poor character win elections, accumulate riches, or achieve unprecedented popularity, the obvious question is whether character ultimately matters, or did it ever?
19:17It did, or at least so we said. Regardless of what they say or write, the people of every era consider themselves less worthy than those who came before. Reading literature, admiring architecture, or squinting in the sunlight at imposing statues of intimidating personalities of old, we believe they were wiser, braver, and better than we are now. Explorers, inventors, queens, soldiers, and all those who shaped their respective epochs had character. We stand in reverence of Tom Brokaw's greatest generation and admit that we're unsure we could or would do the same today. We have reason to feel this way.
20:11For centuries, we've told stories, painted pictures, written poetry, and sung of men and women of character. As a child, I was told young George Washington could wield an axe well enough to cut down a cherry tree, but was incapable of lying about the deed. We are long haunted by the shadow of our forebears. We admire leaders like Lincoln. The Catholic Church has elevated more than 10 ,000 saints whose acts, faith, and character serve to inspire. Countless children are named not for eccentric Uncle Leo, but for those whose character their parents hope they will someday emulate. Our fascination with character is more than idle celebrity worship.
21:03There has always been an intuitive understanding that life in the world, as English philosopher Thomas Hobbes described it, could be solitary, poor, nasty, brutish, and short. Incentives abound to reward power and wealth, while only a fragile web of ethics, values, and social mores, often connected to religion, reinforces concepts of justice, mercy, generosity, and benevolence. Without the pull of character on a person's conscience, things could be a lot worse. In the past, people were expected to behave with admirable character, even if only superficially. Integrity was openly demanded, and countless duels were fought over questions of honor.
22:00Newspapers and pamphlets routinely charged prominent people with misbehavior, and the articles were reliably followed by strident denials and counter-accusations. America's founding fathers, a gifted but often thin-skinned collection of patriots, claimed to be guided by an ideal of character, but also masterfully constructed a system of governance that accounted for a lack of it. In most ways, the innate character of our ancestors differed little from our own. The world knew cruelty, greed, and hatred in doses we can scarcely comprehend today, and they constructed an imperfect but still valuable latticework of rules, norms, and ideals that sought to control things as best they could.
22:54They were aided by physical limitations of their era. Information moved with increasing speed, but, relatively speaking, remained glacially slow. As books and then newspapers became economically viable, standards of journalism emerged unevenly, but their importance was recognized. While the world-watched figures like Adolf Hitler leveraged organs of government and tools of influence with stunning effectiveness, it became apparent that the concept of character was central to preventing a world dominated only by strength. Character has never been perfect. Heroes were often also slaveholders, philanderers, or crooks.
23:45But there was an understanding that while we could pretend not to notice these misdeeds and shortcomings, it was essential that there be a standard. We might rarely, if ever, embody the ideal of character, but some set of benchmarks should enact a gravitational-like pull to a higher plane. We may periodically be despicable, but we should feel guilty when we do. That is the importance of character. Superficial talents or qualities can confuse us about who a person really is, even when we are that person. Character is revealed and sometimes shaped by situations, especially when we must make fundamental choices about right and wrong, obligation over advantage and courage over cowardice.
24:43The West Point Cadet Prayer captures the essence of behaving as we should, regardless of the costs. Make us to choose the harder right instead of the easier wrong, and never to be content with a half-truth when the whole can be won.
25:04Thanks 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. I'll see you next episode.
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In the past, character wasn’t just admired, it was expected. People demanded integrity, and even fought duels over questions of honor. But today, does character still matter?
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.
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Audio excerpted courtesy of Penguin Random House Audio from ON CHARCTER by General Stanley McChrystal, read by General Stanley McChrystal. © 2025 McChrystal Group LLC, ℗ 2025 Penguin Random House, LLC. All rights reserved.
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