This Isn’t A Solo Journey | Does Character Still Matter?

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.📖 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=-_pBw1clQ8sAudio 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 Facebook 📢 Share | ⚙️ Manage Subscription

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

• 0:04Ryan Holiday?

  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, 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.

• 0:42Ryan Holiday?

  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, 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 Cypionic Circle, a group of Roman politicians and philosophers who met at the House of Cypio, 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,

• 1:24Ryan Holiday?

  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. 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

• 2:08Ryan Holiday?

  Can be ruined by not so great influences. That was Epictetus's 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 preorder now. We've been talking about it. There's just a couple of weeks left and it would mean a lot if you did. That's at dailystoic.com/wisdom. The idea is that wisdom, like success, isn't a solo journey. It requires community and discourse and the friction that comes with engaging with other minds.

• 2:53Ryan Holiday?

  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. And 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 Socratic circle. You know, usually when I get to meet my readers,

• 3:37Ryan Holiday?

  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/preorder. There's a bunch of bonuses 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.

• 4:18Ryan Holiday?

  Hey, 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 Thirty Tyrants. The ancient Stoics lived in the time of Nero, and Cato lived in what's Israel called the dregs of Romulus. Mark Sereless was there for the decline and fall of the empire.

• 5:04Ryan Holiday?

  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, 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 step 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. So it's On Character by General Stanley McChrystal. The subtitle is Choices

• 5:45Ryan Holiday?

  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, since he left the army, you know, has done his share of consulting and advising. He's built a big company, he's worked with a lot of interesting organizations. If

• 6:26Ryan Holiday?

  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. 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.

• 7:10Ryan Holiday?

  If you don't know who General McChrystal is, he's a retired US 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. 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. Actually, let me play you that little chunk here because I asked him about this specifically.

• 7:57Ryan Holiday?

  I've always thought is interesting about you because 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, 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.

• 8:40Ryan Holiday?

  That closing of your career, 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. All these things can happen to you, but the harm is if, 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.

• 9:04Speaker 01

  Yeah, thanks for bringing it up. I, I in no way compare myself to James Stockdale.

• 9:08Ryan Holiday?

  Yes.

• 9:09Speaker 01

  But if I think about his experience where he lost control over everything about his physical wellbeing and, and in short term, almost everything, he chose not to let that re-identify him, change who he was.

• 9:24Ryan Holiday?

  Yes.

• 9:25Speaker 01

  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.

• 9:49Ryan Holiday?

  Could be in Steve Bannon's war room right now.

• 9:52Speaker 01

  Exactly. And instead made the decision with the help of my wife, Fanny, not to do that.

• 9:58Ryan Holiday?

  Yeah.

• 9:59Speaker 01

  Instead to say, okay, I am not a bad person. And so I'm going to be as good a person as I can be going forward. That became really liberating.

• 10:08Ryan Holiday?

  Yeah.

• 10:08Speaker 01

  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.

• 10:15Ryan Holiday?

  Yeah.

• 10:16Speaker 01

  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.

• 10:26Ryan Holiday?

  Yeah.

• 10:27Speaker 01

  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 successes. 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.

• 10:54Ryan Holiday?

  Right.

• 10:55Speaker 01

  And then I have opportunities and I have the opportunity to be whatever I will myself to be.

• 11:01Ryan Holiday?

  Yeah.

• 11:02Speaker 01

  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.

• 11:13Ryan Holiday?

  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's 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 Stoic Podcast.

• 11:45Speaker 02

  Does character still matter? Character is more essential than ever to our world.

• 11:53Speaker 02

  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.

• 12:21Speaker 02

  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, be nothing more than an ideal? Is it dead, dormant, or simply difficult?

• 12:56Speaker 02

  I was blessed to have loving parents of admirable character, mostly good sports coaches, and later some excellent military commanders.

• 13:07Speaker 02

  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.

• 13:32Speaker 02

  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. 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 hollers out our faith in their character.

• 14:13Speaker 02

  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. 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 hoped to be, when our ambition, ego, impatience, and greed led us to act in ways we might describe as out of character.

• 14:50Speaker 02

  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? It 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

• 15:35Speaker 02

  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. For centuries, we've told stories, painted pictures, written poetry, and sung of men and women of character.

• 16:17Speaker 02

  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 forbears. 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.

• 16:55Speaker 02

  Our fascination with character is more than idol-celebrity worship.

• 17:01Speaker 02

  There 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.

• 17:42Speaker 02

  In the past, people were expected to behave with admirable character, even if only superficially.

• 17:50Speaker 02

  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. 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.

• 18:26Speaker 02

  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. Information moved with increasing speed, but, relatively speaking, remained glacially slow. As books and then newspapers became economically viable, standards of journalism emerged unevenly,

• 19:12Speaker 02

  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 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.

• 19:54Speaker 02

  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.

• 20:13Speaker 02

  That is the importance of character.

• 20:17Speaker 02

  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. The West Point cadet prayer captures the essence of behaving as we should, regardless of the costs.

• 20:49Speaker 02

  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.

• 21:01Ryan 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.