This Is How You Always Win | NPR On Point

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

• 0:02Ryan Holiday?

  Welcome to the Daily Stoic Podcast, where each day we read a passage of ancient wisdom designed to help you in your everyday life. Well, on Thursdays, we not only read the daily meditation, but we answer some questions from listeners and fellow Stoics who are trying to apply this philosophy just as you are. Some of these come from my talks, some of these come from Zoom sessions that we do with Daily Stoic Life members, or as part of the challenges. Some of them are from interactions I have on the street when there happened to be someone there recording. But thank you for listening, and we hope this is of use to you.

• 0:45Ryan Holiday?

  This is how you always win. We've come up with many sayings in short hands to rationalize and justify the things we do to get ahead. Winning isn't everything, it's the only thing. Win at all costs. Look for every advantage. If you're not cheating, you're not trying. Everyone does it. What they don't know doesn't hurt them. And the most seductive, no one will ever know. In Montaigne's time, there was a popular saying that went, "It is always glorious to conquer, whether the victory is achieved by chance or skill." But in his essays, Montaigne rejects the idea. "The philosopher Chrysippus would not have been of that opinion, and I just as little," he writes. "For used to say that those who run

• 1:28Ryan Holiday?

  a race should indeed employ their whole powers and strength for speed, but that nevertheless it was not in the least permissible for them to lay a hand on their adversary to stop him, or to stick out a leg to make him fall." Chrysippus was actually the third leader of the Stoic school, and he gained notoriety in the ancient world by competing as a distance runner in the Olympic Games. He once explained, as Montaigne mentions, and as I have a whole section about in Right Thing Right Now, that he had a unique philosophy as far as competition. "Runners in a race ought to compete and strive to win as hard as they can," he said. "But by no means should they trip their competitors or give them a shove. So too in life, it is

• 2:11Ryan Holiday?

  not wrong to seek after the useful things, but to do so while depriving someone else is not just. Without a sense of honor, without a commitment to rules or fairness, you might win." But you'll always lose and be a kind of loser. In sports and in life, a stoic takes responsibility. They play the ball where it lies. They pay what they owe. We disclose the conflict of interest. They call the penalty on themselves. They help out a competitor. They achieve their victory by skill, by employing their whole powers and strengths, not by cheating, tripping, or depriving someone else. And this might seem crazy to some people, and it may cost us something. And again, we may sometimes lose because of it. But we won't lose what's important. We'll win what really matters.

• 2:55Ryan Holiday?

  We'll win our own self-respect, the ability to be proud of ourselves, to look in the mirror. We might not always get a great reputation for this. But as the Stoics would say, at least we'll deserve one. This idea of the standards you hold yourself to, how you judge your own success or failure, the rules you observe, again, not making little distinctions between advantages and cheating. This is, to me, the Stoic idea of justice, right? It's not what happens in a court of law, but it's a philosophy that we try to guide our life by. And that's the new book, Right Thing Right Now: Good Values, Good Character, Good Deeds. There's a whole chapter about this thing with Christippis.

• 3:39Ryan Holiday?

  I talk about some modern sports examples in there, some stories I think you'll really like. And I think it's important we see the Stoics loved sports, and they saw it as a way of understanding the world and learning lessons, just as we do now. Anyway, we've still got all those preorder bonuses. We're extending that for a couple more days. You can grab that, dailystoic.com/justice. Grab the book in any format, ebook, physical. We've got some signed first editions. And if you've already got the book, maybe it shipped earlier or whatever. If you've already got the book, it would mean so much to me if you could leave a review. That helps a bunch, too. dailystoic.com/justice. Check out the new book. I'll talk to y'all soon.

• 4:20Ryan Holiday?

  Hey, it's Ryan Holiday. There was just this cool story on NPR's On Point. They did a special deep dive into Stoicism and they talked to Nancy Sherman, who I'm a big fan of, and also Margaret Graver, two experts on the philosophy, of course, academic experts, which I very obviously am not. But they also interviewed me and that was cool. That was a cool experience. But sometimes when you're listening to something on TV or the radio, you don't get to see the whole thing. Like, I just did the Today Show on Monday, which was a really cool experience, and I had four minutes to talk about ancient philosophy. That's not a lot of time. I had four minutes to get through this complex philosophy, let alone get to the themes in the Justice Book. Four minutes. That's tough.

• 5:03Ryan Holiday?

  As I walked in and I saw Carson Daly, who follows The Daily Stoic, he was like, "Man, this is going to be tough. Four minutes is not enough time." And this NPR interview, it was a similar thing. They had basically four minutes. We talked for about 30 minutes. The very nice producer was asking me a bunch of questions. He's like, "I'm probably going to take three to four 30-second snippets from this and run it." Even in this hour-long piece, like to split it up in three experts plus a producer, nobody gets that much time. So you can't go in-depth as you want to go. And sometimes stuff gets cut. Sometimes they gravitate towards this or that. I thought it was a great story. It's not all positive for me, I guess. There's probably some little jabs here or there, but whatever. What I wanted to bring you was kind of a behind-the-scenes. And also, I really liked some of my answers. And then, because here on Thursdays,

• 5:46Ryan Holiday?

  we do these Q and A episodes, I wanted to bring you, like, the stuff that ended up on the cutting room floor and my fuller answers. So I asked her if I could have the auto file from our Zoom conversation, which she was nice enough to do. She didn't want her voice to be in, which I totally understand, but I wanted to bring you my answers to those questions. So the first question she was asking me was, you know, "Why is Stoicism having a resurgence now?"

• 6:13Ryan Holiday?

  I think there's, there's no question that when you have tools that spread ideas very quickly, you're going to see a resurgence in ideas that have always been there, that resonate with people, good ideas and bad ideas, right? There's always sort of been these ideas that pop up in different times. I think that's part of it. There's a great quote from Flaubert that I think about. He says, you know, there was this moment, he says, between Cicero and Marcus Aurelius, he said, "When the gods had died out, but Christ had not yet come," he said, "that man stood alone in the universe." He was pointing to sort of the pinnacle time of Stoic philosophy, that, that period. He's not exactly right on all the dates and names, but he was

• 6:56Ryan Holiday?

  saying, I think, as old systems fall away, people look backwards to try to find truths and strategies and things to build. They're looking for answers. They're looking what they should build their, you know, their values and their characters on. And, and I think, you know, we've seen a collapse in trust in so many different institutions. You know, schools don't teach the humanities the way they once did, and people have turned away from the church. And so, philosophy as a guide to the good life, how to be a good person and how to flourish as a person, I think, takes on a new resonance and a new urgency in a world

• 7:39Ryan Holiday?

  of similar sort of decline, and then also, as you said, you know, turbulence and dysfunction.

• 7:47Ryan Holiday?

  And then another thing we touched on was like, how does philosophy continue to be reinterpreted? What is it that we decide to carry forward and what do we leave behind? One of the things that's so interesting, and it only hit me somewhat recently, is realizing that to Marcus Aurelius, Stoicism was ancient philosophy, right? So he's, he's living in, you know, the, the mid 160s AD, this is the sort of height of his reign, and, you know, Zeno is writing and thinking around the turn of the fourth century. So it's hundreds of Old to him. And so it is already evolved and changed so much in those centuries.

• 8:28Ryan Holiday?

  Of course, it should change and evolve in the centuries since. And I do think the Stoics would have taken advantage of or updated their assumptions around breakthroughs we've made, not just like medically and psychologically, but we have to understand that so many of the things that we take for granted today from a values perspective were also invented, right? Or the idea that hey, slavery is wrong, or the idea that it's a bad system to have one guy be the most powerful person in the world. Obviously, at some point in the Roman Empire, they understood this and then they they lose sight of this. But of course, I think they would

• 9:10Ryan Holiday?

  update. And so I have no problem saying, look, these were men and women who got a lot of things right thousands of years ago, but they did live in a different world built around different assumptions. And we shouldn't be afraid to update and adjust. The philosopher that Seneca quotes the most is Epicurus, the guy who is ostensibly his rival. And he says, Look, I'll quote a bad author if the line is good. He says, I'll read like a spy in the enemy's camp. And so I think the Stoics would have been much more open minded and flexible if they were alive today than maybe

• 9:49Ryan Holiday?

  some of what you might call the Stoic fundamentalists or originalists try to try to claim.

• 9:58Ryan Holiday?

  And then they asked me about this idea of Broism, you know, Stoicism as a male centric philosophy, a masculine philosophy, what some of the critics, including what Nancy and Margaret, I think rightfully call out in some ways. Well, what were my thoughts on that? And this is what I said.

• 10:16Ryan Holiday?

  Well, I'm of two minds. I would say of the things to be worried about in our crazy messed up world, the idea that people in technology are availing themselves of ancient wisdom, particularly wisdom built around courage and self-discipline and justice and wisdom, that does not strike me as, as one of the trends I'm most concerned about, you know? I think it's good. I want more people to read Stoicism and I understand it's an entry point into not just all the ideas in Stoicism, but, but philosophy and antiquity in general. At the same time, in a world where there is kind of a grievance culture and there is

• 11:01Ryan Holiday?

  a lot of sort of populism and misinformation out there, are there people who are weaponizing some of these ideas or misusing them, you know, to attract followers? Yeah, I think so. I'm not sure exactly what to do about that. I don't think you would throw the baby out with the bathwater there, but I, I have no problem calling those people out, pointing out that it's perverting the philosophy. And, and, you know, sort of again, also pushing back on this idea that Stoicism is just for men, it's about suppressing and eliminating emotion, that it's an inherently self-interested, self-involved philosophy. This is just disprovable

• 11:41Ryan Holiday?

  on its face. And, you know, I try to do my best to, to point that out when I, when I see it. And, um, yeah, that's kind of how I think about it.