The Daily Stoic - This Isn't A Solo Journey | Does Character Still Matter?

Episode Date: October 5, 2025

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 McChrys...tal 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.📖 Preorder the final book in Ryan Holiday's The Stoic Virtues Series: "Wisdom Takes Work": https://store.dailystoic.com/pages/wisdom-takes-work📚 You can grab signed copies of On Character: Choices That Define A Life by General McChrystal at The Painted Porch | https://www.thepaintedporch.com/🎥 Watch General McChrystal's interview on The Daily Stoic Podcast: https://www.youtube.com/watch?v=-_pBw1clQ8s👉 Support the podcast and go deeper into Stoicism by subscribing to The Daily Stoic Premium - unlock ad-free listening, early access, and bonus content: https://dailystoic.supercast.com/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.🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.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, Twitter, YouTube, TikTok, and FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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Starting point is 00:00:00 Look, ads are annoying. They are to be avoided, if at all possible. I understand as a content creator why they need to exist. That's why I don't begrudge them when they appear on the shows that I listen to. But again, as a person who has to pay a podcast producer and has to pay for equipment and for the studio and the building that the studio is in, it's a lot to keep something like The Daily Stoic going. So if you want to support a show, but not listen to ads. Well, we have partnered with Supercast to bring you a ad-free version of Daily Stoic.
Starting point is 00:00:40 We're calling it Daily Stoic Premium. And with Premium, you can listen to every episode of the Daily Stoic podcast, completely ad-free. No interruptions, just the ideas, just the messages, just the conversations you came here for. And you can also get early access to episodes before they're available to the public. And we're going to have a bunch of exclusive
Starting point is 00:00:59 bonus content and extended interviews in there just for Daily Stoic Premium members as well. If you want to remove distractions, go deeper into Stoicism and support the work we do here. Well, it takes less than a minute to sign up for Daily Stoic Premium, and we are offering a limited time discount of 20% off your first year. Just go to dailystoic.com slash premium to sign up right now or click the link in the show descriptions to make those ads go away. Welcome 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,
Starting point is 00:01:44 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. This 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,
Starting point is 00:02:23 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 Sipionic 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 transcendentalist, a movement which Emerson started in Concord in 1836, or the lost generation who came of age together in Paris after World War I. Think of the Bloomsbury Group in 20th century London or the PayPal Mafia in Silicon Valley or the grunge scene in Seattle.
Starting point is 00:03:04 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. That was Epictetus's observation. If you live with the lame man, you will start to limp.
Starting point is 00:03:43 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.
Starting point is 00:04:13 It 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 understand. stands 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. And it's going to be a small gathering, just a handful of us. We're going to sit down
Starting point is 00:04:55 and talk about virtue and philosophy, as they did 2,000 years ago in the Sipionic 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's 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 pre-order. There's a bunch of bonuses
Starting point is 00:05:26 in there. I think it'll be great. I'm looking forward to meeting you. Tacking this on, 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. Hey, it's Ryan. Welcome to
Starting point is 00:05:45 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 Stokes lived in the time of Nero, and Cato lived in what Cicero called the Dregs of Romulus.
Starting point is 00:06:26 Mark Cyrillus was there for the decline and fall of the empire. Seneca literally watched Rome burned. 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 one experience. And one of the books I recommended at the end of that list was this book, which I think was
Starting point is 00:07:03 one of the best books I read in the last year. So it'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, you know, 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,
Starting point is 00:07:40 since he left the army, you know, is done his share of consulting and advising. He's built a big companies, 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, and so was his publisher.
Starting point is 00:08:24 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.
Starting point is 00:08:47 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. I'm sure he would concede that he made mistakes there, that he wished it 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.
Starting point is 00:09:14 Actually, let me play you that little chunk here. because I asked him about this specifically. I've always thought as interesting about you because, you know, we live in this, or 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.
Starting point is 00:09:36 Whatever. It's this breaking point in their public persona, their life, where the resulting person is bitter or angry or grieved. 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.
Starting point is 00:10:08 One of the things that Stoics talk about is they go, they say it can only harm you if it harms your character, right? That basically you can lose the job, you can lose your career, you can lose all your money, can happen to you. But the harm is if it turns you into something that you're not. And I feel like you just went in a different direction than so many people in that position. Yeah, 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,
Starting point is 00:10:42 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. Could be in Steve Bannon's war room right now.
Starting point is 00:11:18 Exactly. And instead made the decision with the help of my wife, Fannie, 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. That became really liberating. Yeah. And the thing that was important to remember is you don't do away with the injury.
Starting point is 00:11:39 You can't pretend it didn't happen. It did happen. Yeah. 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. That'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'd 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 a war, I had lost no limbs. I wasn't killed. I wasn't, you know, in other ways, damage. So I don't have much complaint 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.
Starting point is 00:12:39 So 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. We were just at a dinner with some friends, and they were talking about their sort of pregame. partying routine now that they're a little older. And one of them was saying that they take actually today's sponsor, pre-alcohol.
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Starting point is 00:14:06 any reason, they'll refund your money, no questions asked. Just remember to head over to zbiotics.com slash stoic, the news code stoic, they check out for 15% off. So something you might not know about me. I live on a Halloween street here in Bastrop. Like they close the whole street down and there's decorations everywhere. People go absolutely insane. Thousands of people from all over this enormous county, mostly farm kids that can't trick or treat where they live, come out and it's crazy. So we're already putting up our Halloween decorations. We're already going all out. And that's where today's sponsor comes in. Wayfair. Not only did we look at our Halloween decorations, but we already started looking at Christmas decorations too. Wayfair makes it easy to tackle
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Starting point is 00:15:28 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.
Starting point is 00:15:56 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. Could character be the same? Might what we venerate, the bedrock of values supporting a superstructure of worthy behaviors,
Starting point is 00:16:28 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,
Starting point is 00:17:04 and an unequivocal honor code, I wouldn't have been able to dodge thinking about character. Then 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.
Starting point is 00:17:30 We're also disappointed when leaders we assume, 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 hollers 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.
Starting point is 00:18:06 Still, 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 hope 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
Starting point is 00:18:37 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. It did, or at least so we said. Regardless of what they say or right, the people of every era
Starting point is 00:19:02 consider themselves less worthy than those who came before. Reading literature, admiring architecture, or squinting in the sunlight and imposing statues of intimidating personalities of old, we believe they
Starting point is 00:19:18 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.
Starting point is 00:19:47 For 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. There has always been an intuitive understanding that life in the world, as English philosopher
Starting point is 00:20:45 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. Newspapers and pamphlets routinely charged prominent people with misbehavior, and the articles were reliably followed by strident denials and counter-accusations.
Starting point is 00:21:47 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. They were aided by physical limitations of their era.
Starting point is 00:22:35 Information moved with increasing speed, but, relatively speaking, remained glacially slow. As books and the newspapers became economically viable, standards of journalism emerged unevenly, but their importance was recognized. While the world-watched figures like Adolf Hitler leverage organs of government and tools of influence with stunning effectiveness, it became apparent that the concept of character
Starting point is 00:23:07 was central to preventing a world dominated only by strength. Character has never been perfect. Heroes were often also slaveholders, philanderers, or crooks. But there was an understanding that while we could pretend not to notice these misdeeds and shortcomings, it was essential that there be a standard.
Starting point is 00:23:33 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
Starting point is 00:23:59 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. The 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
Starting point is 00:24:32 and never to be content with a half-truth when the whole can be one. 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.

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