The REAL Difference Between Stoics and Cynics | Cynicism Expert Inger Kuin (PT. 2)

What can Diogenes teach us about the roots of Stoicism? In today’s episode, Ryan and classicist Inger Kuin break down the real gap between Stoicism and Cynicism, discussing why one trusted order and structure while the other thought most of society was nonsense. They get into Diogenes’ legendary stunts, the Stoics’ attempt to distance themselves from him, and why the world still needs people who question absolutely everything. Inger Kuin https://ingerkuin.com/ is a researcher, writer, and teacher focused on the intellectual history of ancient Greece and Rome. She is Associate Professor of Classics at the University of Virginia https://classics.as.virginia.edu/inger-ni-kuin. Originally from The Netherlands, she publishes both in English and in Dutch. Check out Inger’s website: https://ingerkuin.com/ Be sure to pick up a copy of Inger’s new book Diogenes: The Rebellious Life and Revolutionary Philosophy of the Original Cynic https://www.amazon.com/Diogenes-Rebellious-Revolutionary-Philosophy-Original/dp/1541606477. 📚 Books that Ryan recommended to Inger: Tales of Soldiers and Civilians: and Other Stories by Ambrose Bierce https://www.thepaintedporch.com/products/tales-of-soldiers-and-civilians-and-other-stories-penguin-classics?_pos=1&_sid=9b0986a10&_ss=r Thoughts of a Philosophical Fighter Pilot by James Stockdale https://www.thepaintedporch.com/products/thoughts-of-a-philosophical-fighter-pilot-volume-431-hoover-institution-press-publication?_pos=3&_sid=988d41b7f&_ss=r Moral Ambition by Rutger Bregman https://www.thepaintedporch.com/products/moral-ambition-stop-wasting-your-talent-and-start-making-a-difference-1?_pos=1&_sid=45d1aafc0&_ss=r 🎟️ Come seeRyan Holiday LIVE https://www.dailystoiclive.com/: https://www.dailystoiclive.com/ Seattle, WA - December 3, 2025 https://www.eventbrite.com/e/daily-stoic-live-onstage-with-ryan-holiday-tickets-1830976292379?aff=oddtdtcreatorSan Diego, CA - February 5, 2026 https://www.eventbrite.com/e/daily-stoic-live-onstage-with-ryan-holiday-tickets-1527497619499?aff=oddtdtcreatorPhoenix, AZ - February 27, 2026 https://www.eventbrite.com/e/daily-stoic-live-onstage-with-ryan-holiday-tickets-1830981698549?aff=oddtdtcreator 👉 Support the podcast and go deeper into Stoicism by subscribing toThe Daily Stoic Premium https://dailystoic.supercast.com/ - unlock ad-free listening, early access, and bonus content:https://dailystoic.supercast.com/ 🎥 Watch the video episodes onThe Daily Stoic YouTube channel https://www.youtube.com/@DailyStoic/videos:https://www.youtube.com/@DailyStoic/videos 🎙️ Follow The Daily Stoic Podcast onInstagram https://www.instagram.com/dailystoicpodcast/?hl=en:https://www.instagram.com/dailystoicpodcast ✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email athttps://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.

• 0:03Ryan Holiday?

  Welcome to the weekend edition of The Daily Stoic. Each weekday, we bring you a meditation inspired by the ancient Stoics, something to help you live up to those four Stoic virtues of courage, justice, temperance, and wisdom. And then here on the weekend, we take a deeper dive into those same topics. We interview Stoic philosophers. We explore at length how these Stoic ideas can be applied to our actual lives and the challenging issues of our time. Here on the weekend, when you have a little bit more space, when things have slowed down, be sure to take some time to think, to go for a walk, to sit with your journal,

• 0:46Ryan Holiday?

  and most importantly, to prepare for what the week ahead may bring.

• 0:54Ryan Holiday?

  Hey, it's Ryan. Welcome to another episode of The Daily Stoic Podcast. In some ways, the bane of my existence is what people think the word Stoic means. Right? I think I say this in the intro of The Daily Stoic. Like, not only is Stoic an unappealing and misunderstood word to most people, particularly in America, but Stoic philosophy doubles it, right? Adding the philosophy on the end means people go, ugh, right? And I've been battling this since I went out with the book proposal of "The Obstacle is the Way." Are people actually going to be interested in this when they have these preconceived notions of what these words mean?

• 1:35Ryan Holiday?

  And of course, Stoicism is not the only school where this is true, right? Epicureanism seems to mean hedonism to people, or gluttony, or even, in the ancient world, this was a problem. Like, Epicurus was presented, even by some of the Stoics, as this, like, perverted weirdo who was corrupting people and living in, you know, sin and excess, which of course, this is not what Epicureanism is about at all. Now, the same is true for cynicism.

• 2:08Ryan Holiday?

  At least epicureanism sounds fun, right? Cynicism sounds negative and short sighted and small minded and sarcastic and rude and mean and all these things, right? But like with lowercase Stoicism and uppercase Stoicism, lowercase cynic and uppercase cynicism have very different origins, very different meanings, and the schools are not that different from each other. I think it was Marshall, the Roman poet, said, "The difference between the Stoics and the cynics is that there's a shirt between them," meaning that the Stoics were a little better dressed than the cynics. Diogenes the Cynic, who we're going to talk about in today's episode, was a transgressive,

• 2:51Ryan Holiday?

  rebellious, fascinating figure. But actually Stoicism would be impossible without cynicism. Zeno's first teacher was a guy named Crates. The founder of Stoicism was tutored by a philosopher named Crates, and also his wife was a fascinating cynic philosopher. Crates was known as the door opener. I talk about him in Wisdom Takes Work. He's the door opener who opens the door to philosophy for Zeno. So in today's episode, which is actually part two, part one, I ran earlier in the week. My guest, Professor Inger Kuin, talked about cynicism versus epicureanism versus Stoicism. Talked about the invention of this lowercase cynic, where the cynics might actually have things more right than the Stoics.

• 3:36Ryan Holiday?

  Then I want to recommend some books, because when we walked through the bookstore, she and I continued this conversation and ended up talking about philosophy quite a bit more. As I said in part one, Professor Kuin is a researcher, writer, and teacher focused on the intellectual history of ancient Greece and Rome. She's an associate professor of classics at the University of Virginia, home of Gregory Hayes, also my favorite translator of meditations. She's originally from the Netherlands, so she publishes in English and Dutch. You can go to her website, ingerkuin.com. And be sure to pick up her book, Diogenes, The Rebellious Life and Revolutionary Philosophy of Diogenes the Cynic. I really liked this conversation. I really liked her, and I think you will like this episode. Do check it out. And as I said, please come see me.

• 4:21Ryan Holiday?

  I'm going to be in Seattle here very shortly. I'm giving a talk on December 3rd, I believe, at Seattle. You can buy tickets at DailyStoic.com. And then I'm going to be in San Diego and Phoenix in February. Grab all of that at DailyStoicLive.com.

• 4:38Ryan Holiday?

  So let's talk the difference between the Stoics and the Cynics, because the Stoics sort of directly descend from the Cynics. I mean, Zeno's teacher is Crates, the cynic. So how does this happen? And what do you see as the major differences between them?

• 4:55Speaker 01

  Okay, this is a great question. A big one, big one. So, I mean, essentially, what happens is that Zeno founds his own school.

• 5:04Ryan Holiday?

  Yeah.

• 5:04Speaker 01

  Right? And, and, and, and comes to be known as, as, as the Stoics after the place where they meet, as is all sort of well, well known. And what, so, so I would say there's sort of two, there's sort of a, a big philosophical difference between the two. And then there is, shall we say, a historical difference between the two.

• 5:26Ryan Holiday?

  Okay.

• 5:27Speaker 01

  Right? Where, where the Stoics were quite invested in distinguishing themselves from the Cynics.

• 5:33Ryan Holiday?

  Yeah.

• 5:33Speaker 01

  And saying like, we are doing our own thing. We are doing something different, right? This is important to them precisely because the Cynics were the guys who lived in the street.

• 5:41Ryan Holiday?

  Yeah.

• 5:41Speaker 01

  Right? So, so that's, that's where that comes from. The same time-

• 5:45Ryan Holiday?

  Like, we're not the sexual perverts like them.

• 5:47Speaker 01

  Yeah, exactly. At the same time, the Stoics cannot really deny their connection to the Cynics, because then they cut their own tie to Socrates. And sort of Socrates as the important forefather of, of living a contemplative life, of philosophy, is a forebear that the Stoics do want.

• 6:07Ryan Holiday?

  Right.

• 6:08Speaker 01

  Which means that they have to accept the genealogy from Socrates to Antysinnes to Diogenes to Crates to Zeno.

• 6:15Ryan Holiday?

  Got it.

• 6:15Speaker 01

  Right? So they are in this bind, right? Where they're both wanting to underplay the connection, but they can't completely deny it. So, so, yeah. So in a historical sense, it's clear that, that-

• 6:27Ryan Holiday?

  Descends from the other.

• 6:28Speaker 01

  Exactly, exactly. And that, and that Crates himself in person was a student of Diogenes. They lived at the same time. And that Zeno then lives at the same time as Crates and is a student-

• 6:39Ryan Holiday?

  Yeah.

• 6:39Speaker 01

  -of, of Crates. So that all sort of works, works just fine and from a historical perspective. Then, in addition to sort of needing this, needing this distance, there's also pretty fundamental differences philosophically. And I think the, sort of the most- Impactful difference ultimately is that for the Stoics, there is a divine organizing principle that is at the heart of everything. And that means that the world is ultimately well organized, right? To put it a little bit in a banal way, right? But for the Stoics, ultimately, there is the understanding that the world is well organized,

• 7:24Speaker 01

  such as it is.

• 7:25Ryan Holiday?

  Yeah.

• 7:25Speaker 01

  And the thing to do is to understand this organization and then to bring yourself, bring your inner self in line with this organization, simply put. Now, for the cynics, there is no such overarching organizing principle, right? There is no divine organizing principle that that ties it everything together. And for the cynics, that also means that the status quo, the world that we live in, such as this today, is not necessarily the best of all outcomes, right? And Diogenes and the cynics, they definitely love the world, right? They think that the human body is an awesome thing in terms of everything that it can do.

• 8:09Speaker 01

  They admired the natural world. They admired the fact that the sun warms us, that we can drink water from the river, that that sort of we, that animals are able to take care of themselves and find food just like that. And if we are a little bit more like that, then then we can live a good life.

• 8:28Ryan Holiday?

  Yeah.

• 8:28Speaker 01

  With what nature has, has given us.

• 8:30Ryan Holiday?

  Living in accordance with nature.

• 8:31Speaker 01

  Yeah, exactly, exactly. But beyond that, there's nothing about this world that's necessary, right? So when it comes to the social structures, the city that we live in, sort of the sort of societal institutions, for the cynics, these are not necessary. Precisely because, for instance, animals seem to be able to do without them quite well, right? And that sort of, and that has a lot of downstream consequences in terms of how,

• 9:03Speaker 01

  How Diogenes thinks about kingship and how he thinks about rulership.

• 9:07Ryan Holiday?

  Right.

• 9:08Speaker 01

  Whereas for the Stoics, it makes a lot of sense to live in an autocracy because ultimately there is one divine organizing principle in the cosmos. So why would there not be an emperor on earth?

• 9:21Ryan Holiday?

  It's like one believes in order and systems and logic and the other is a little bit more random and anarchic that like, hey, this is all made up and you can choose to believe in the made upness, but you don't have to. It doesn't mean anything. This is just how things are. God didn't make them this way and they don't have to remain this way.

• 9:43Speaker 01

  Exactly. Yeah, exactly. So, so the, the society that we live in, the status quo is not God given, is not divine.

• 9:52Ryan Holiday?

  That's not part of nature.

• 9:53Speaker 01

  Exactly. It's not part of nature and, and sort of, and any, anything that's not part of nature for the cynics is open to questioning.

• 10:01Ryan Holiday?

  Right.

• 10:02Speaker 01

  And, and is, you know, is not necessary.

• 10:05Ryan Holiday?

  And this would include things like the moral order, like, hey, this is why you can't masturbate in public. People are like, you can't do it. And Diogenes is like, why not? You know? And, and so there, it does, yeah, it's like, one believes there's such a, you know, that Margaret Thatcher thing where she says, uh, there's no such thing as society. There's just individuals and their families. Right?

• 10:23Speaker 01

  Yeah.

• 10:24Ryan Holiday?

  Although she's obviously coming at it from a very, but Diogenes is saying like, this is all made up. You can do whatever you want. And the Stoics are like, no, no, no, there's a reason for all of this. And whether there is a reason or not, probably have some fundamental fear of the anarchy that comes if you question it. So it's like, even if there is no reason, this is better than the alternative. So let's, there's a conservatism to Stoicism that maybe isn't lowercase conservatism to Stoicism that is not there in Diogenes.

• 10:56Speaker 01

  Yeah. Yeah. Yeah. Absolutely. And I think sort of when you, when you said earlier about masturbating in the, in the market square.

• 11:03Ryan Holiday?

  Yeah.

• 11:03Speaker 01

  As, as a moral question.

• 11:06Ryan Holiday?

  Yeah.

• 11:06Speaker 01

  I think Diogenes would say it's a question of etiquette.

• 11:09Ryan Holiday?

  Right?

• 11:09Speaker 01

  It's not a moral question, right?

• 11:11Ryan Holiday?

  Right.

• 11:11Speaker 01

  Like, moral questions are about justice.

• 11:14Ryan Holiday?

  Yes.

• 11:15Speaker 01

  Right?

• 11:15Ryan Holiday?

  Sure, sure.

• 11:16Speaker 01

  And about, you know, and about-

• 11:17Ryan Holiday?

  And he's saying etiquette is stupid and it doesn't matter.

• 11:20Speaker 01

  Yeah, exactly.

• 11:20Ryan Holiday?

  Yeah, yeah.

• 11:21Speaker 01

  Exactly.

• 11:21Ryan Holiday?

  And the Stoics are like, yeah, but we're all descending to apes killing each other if there's no etiquette and is morality just another version of etiquette? A more extreme version of etiquette?

• 11:33Speaker 01

  And ultimately, for the Stoics, it's about understanding and making sense of society such as it is.

• 11:40Ryan Holiday?

  Yes.

• 11:41Speaker 01

  Right? In order to adjust to it and in order to sort of lead the most, you know, the most virtuous and dutiful life within that context, within your station, within the city that you live in.

• 11:54Ryan Holiday?

  Yeah.

• 11:55Speaker 01

  Whereas for cynics, we're questioning it to see if maybe there might be a better way to live.

• 12:00Ryan Holiday?

  Is that the fundamental flaw of Diogenes, though? Which is like, he can do it because everyone else buys into the other system. And he is able to exist, not as a parasite, but as a, as an exception to the rule. But if that was the rule, everyone would starve, there would be anarchy, or, or there would be just a lot less people would be able to live, right? Like, you need, for the world that we have it then and now, you need people who go to work every day.

• 12:30Speaker 01

  So I agree with you that if we had a society that consisted solely of Diogeneses, right? That there would be sort of a lack of constructiveness, in a sense, right? There would be a lack of coeur and constructiveness. And, and this would be a problem. The society without Diogeneses-

• 12:52Ryan Holiday?

  Sure.

• 12:53Speaker 01

  -is extremely dangerous.

• 12:56Ryan Holiday?

  Yes. It's Sparta or something.

• 12:58Speaker 01

  Yeah, yeah, because, because if you have a society without any Diogeneses, then there is no pushback, there is no questioning, there is no sort of bringing things back to the human measure and, and sort of deciding, well, but how, how does this affect me and my everyday life? And do we really need to be doing this? Is this, is this really the best of all possible outcomes? And this is, you know, this sort of, again, goes to the heart of this, you know, philosophical- Impurity or ambiguity

• 13:33Ryan Holiday?

  Yeah.

• 13:34Speaker 01

  In in Diogenes in the sense that he does live on the fringes of society and he lives on alms and in order for him to, you know,

• 13:43Ryan Holiday?

  Someone has to be making the money to give to Diogenes.

• 13:46Speaker 01

  Exactly, right? Like there, there, there has to be.

• 13:49Ryan Holiday?

  Somebody made the jar that he lives in.

• 13:51Speaker 01

  Right.

• 13:51Ryan Holiday?

  You know, he doesn't live in a hut. He's not an off the grid survivalist who can do anything for himself. That's what's so interesting about him, right? Like, he's not going off into the woods and living off the land.

• 14:03Speaker 01

  No.

• 14:03Ryan Holiday?

  He is living off the refuse of society.

• 14:07Speaker 01

  Yeah, because.

• 14:08Ryan Holiday?

  That he thinks is stupid.

• 14:09Speaker 01

  Yeah, but exactly. But at the same time, he does think, like, he does still appreciate his fellow humans just enough.

• 14:17Ryan Holiday?

  Yes.

• 14:17Speaker 01

  That he thinks that they are worthy of what he has to say.

• 14:21Ryan Holiday?

  That's true. He's not an antisocial, he's not a hermit in that sense either. He's just, he's just like, why are you going to that job, man? You know?

• 14:31Speaker 01

  Right, exactly, exactly. Like, do you, do you, like, is this, is this a good job? Do you believe in this job? Right? Does that, like, does this job align with your ideas of justice?

• 14:42Ryan Holiday?

  Yeah.

• 14:42Speaker 01

  And if it doesn't, you should stop going to that job because you don't actually need that money. You don't actually need that car.

• 14:48Ryan Holiday?

  You can always live in a jar.

• 14:50Speaker 01

  Exactly, exactly. So, so, and this is ultimately what Diogenes means by freedom, right? Is, is, is the freedom to be able to make those choices and those decisions because you are not afraid of being a beggar and you have taught yourself to be able to live on the street and to live on, on, on very little. And, and, and because you have boiled down life to its essence in that way, right? You are able to be happy with your handful of beans and your, you know, stale bread, right? And that knowledge, that preparation then allows you to be independent and to say to Alexander,

• 15:33Speaker 01

  no, I don't need anything from you. Just get out of my sunlight. That's all I need.

• 15:37Ryan Holiday?

  Well, Diogenes is able to say that to Alexander in a way that Seneca is not able to say that to Nero. And so you go, who's actually gets it right?

• 15:44Speaker 01

  Yeah.

• 15:45Ryan Holiday?

  It's interesting, too, how much this boils down to that expression about the narcissism of small differences. Like, the Epicureans and the Stoics. Way more in common than difference.

• 15:55Speaker 01

  Yeah.

• 15:55Ryan Holiday?

  The cynics and the Stoics way more in common than difference, especially because like, yeah, it's not like the Stoics were like the man and then Diogenes is not the man. First off, because they're obviously, you know, is literally training under one.

• 16:08Speaker 01

  Yeah.

• 16:08Ryan Holiday?

  But like, the Stoics are questioning so many of the assumptions. I also believe you should live in accordance with nature. I think, is it Juvenal who says, um, between the Stoics and the cynics, they have only a shirt between them. And it's like, one, yeah, one is wearing clothes and the other's like, we don't even need clothes. And so it's just like, the degree to the extremes with which you're willing to take it. Like, the Stoics are like, we love all the philosophy stuff, but somebody has to serve in the army and somebody has to clean the streets. And like, somebody has to do this stuff. And Diogenes is saying like, not us, you know? And then I think the Stoics are saying, if we don't do it,

• 16:51Ryan Holiday?

  either nobody's going to do it, or someone worse is going to do it. And that's, I think, one is making this kind of pragmatic, you could say, responsible choice. And it's not that the other is irresponsible, but there is something, I think, both in the Epicureans and in the cynics, that's like, well, we don't want to be bothered with that stuff. We're going to retreat to the garden, or we're going to just answer our questions. But like, somebody else makes sure that the soldiers are manning the city walls.

• 17:33Speaker 01

  So this is where cynicism and Epicureanism have a lot in common in the sense that they withdraw from political life in a way that the Stoics very much did not. At the same time, it's this kind of pragmatism, right? Well, if I don't do this thing, that I have an inkling might be wrong.

• 17:51Ryan Holiday?

  Yeah.

• 17:52Speaker 01

  A worse person will do it.

• 17:53Ryan Holiday?

  Yeah.

• 17:54Speaker 01

  Right? I mean, these are the kinds of decisions that totalitarian regimes are built on. Right?

• 17:58Ryan Holiday?

  Sure.

• 17:58Speaker 01

  So, so.

• 17:59Ryan Holiday?

  But also functioning democracies, right?

• 18:00Speaker 01

  Absolutely. Yes, like both of them.

• 18:02Ryan Holiday?

  Yes, yes, yes.

• 18:03Speaker 01

  Yeah, absolutely. But in the, in the case of a functioning democracy, right? To be able to say, I will do this job.

• 18:10Ryan Holiday?

  Yeah.

• 18:10Speaker 01

  Right? Even though I don't feel like it today.

• 18:13Ryan Holiday?

  Yeah.

• 18:13Speaker 01

  Right? I would rather sleep in. Right? I would say that that's what a functioning democracy is built on.

• 18:18Ryan Holiday?

  Yeah.

• 18:18Speaker 01

  But I will do this job because, you know, and I know it's, I know it's an unjust task that I'm contributing to, right? Because if I don't do it, someone else would do it. Right?

• 18:29Ryan Holiday?

  Right.

• 18:29Speaker 01

  That's like, I don't, you know, I don't, I don't think that's part of a functioning democratic

• 18:35Ryan Holiday?

  Yes.

• 18:35Speaker 01

  regime. And I, and I think that's precisely why Diogenes's thinking is so important, is so powerful.

• 18:42Ryan Holiday?

  Yeah.

• 18:43Speaker 01

  Because, because it forces you to, to ask that question every day. You're absolutely right. They have so much in common, right? The Stoics and the cynics have so much in common.

• 18:52Ryan Holiday?

  Yeah.

• 18:52Speaker 01

  And, and there's so much that the Stoics learned and took from Diogenes and from Crates. And, and this has all to do with, you know, precisely the notion that we should not be afraid of death, the notion that we should actually think about our lives and like spend time thinking about how to live our lives well, that we should not get lost in, in luxury goods, that we really don't need all that much to be happy.

• 19:20Ryan Holiday?

  Right.

• 19:20Speaker 01

  These are all, these are all things that they share.

• 19:23Ryan Holiday?

  Cultivating that kind of resilience. Like, one of my favorite stories about Diogenes is he's seen begging a statue.

• 19:29Speaker 01

  Right, exactly.

• 19:30Ryan Holiday?

  And they go, what are you doing? And he's like, I'm practicing being rejected.

• 19:32Speaker 01

  Exactly.

• 19:33Ryan Holiday?

  And, and you just go, oh yeah, there's, there's this, this idea that like exposure therapy, basically.

• 19:38Speaker 01

  Absolutely.

• 19:39Ryan Holiday?

  Like doing hard, uncomfortable thing. Like Diogenes, you go, he's a homeless person. But that's a difficult existence. I mean, it's cold there in the winter, it's hot in the summer. And he is exposed over the years to the elements. He has a toughness that you're not typically associating with the philosopher.

• 19:58Speaker 01

  Right.

• 19:58Ryan Holiday?

  But he's kind of like, in the way that Marina Abramovic is, is effectively an athlete.

• 20:03Speaker 01

  Yeah.

• 20:03Ryan Holiday?

  He is an athlete in terms of inhabiting the human body and finding out what it's capable of.

• 20:08Speaker 01

  Yeah, exactly. And, and this, and this is, this is what the Stoics and the cynics share. This notion that by preparation, whether that's mental preparation or whether it's bodily preparation.

• 20:20Ryan Holiday?

  Yeah.

• 20:20Speaker 01

  You can. Prepare yourself and therefore be more free and be less afraid because you know that you have that resilience and you know that you're capable of these things. And you know, this is, this is why for Diogenes, it's really important to know that he can live without nice food and live without wine. But once he's trained his body, it's fine to have a glass of wine because he knows he can do without it.

• 20:44Ryan Holiday?

  And he can reject Alexander the Great because other than death, there's nothing Alexander can do to him.

• 20:50Speaker 01

  Right.

• 20:51Ryan Holiday?

  There's nothing Alexander can take from him.

• 20:53Speaker 01

  Exactly.

• 20:54Ryan Holiday?

  And in, he realizes in that moment that that makes him more powerful than Alexander. Or it frees him to speak truth to power that Aristotle cannot, uh, because Aristotle doesn't want to lose his job.

• 21:08Speaker 01

  Yeah.

• 21:08Ryan Holiday?

  Right? And Diogenes doesn't have a job.

• 21:10Speaker 01

  Right.

• 21:11Ryan Holiday?

  And so he's like, you suck, you know? And that there, there's a, an empowerment, the, the, the powerlessness creates an empowerment.

• 21:20Speaker 01

  Exactly. And that's why this, this anecdote is so important and that's why we all love it so much is because it says so much about power that, that power only exists when you let the other person wield power over you in that way. And if you are Diogenes, you don't need anything from Alexander and you are not afraid of him. And that means that even though he's Alexander, his, his power goes up in smoke and Alexander realizes that in that moment. And that's why he's so impressed with Diogenes and this is what he takes with him for the rest of his life. And I mean, I think, we haven't talked about this yet, but I think sort of one of the places

• 22:01Speaker 01

  where you really see the difference between the Stoics and the Senics is when it comes to the question of slavery.

• 22:07Ryan Holiday?

  Yeah.

• 22:07Speaker 01

  And also the difference between Aristotle and Plato and the Senics and the Stoics. Because this is something that was so ingrained in ancient society, was so much a part of everyday life that for the Stoics, it is wallpaper, right? It's, it's, it's part, it's part of society and it's something that they. Cannot, do not venture to think outside of, right?

• 22:32Ryan Holiday?

  Even Epictetus, the slave, doesn't seem to go like, this isn't right. It's more like, it's happening to me, I wish it wasn't happening to me. But, but the idea that the institution itself is an injustice.

• 22:44Speaker 01

  Right.

• 22:45Ryan Holiday?

  It's remarkable how many centuries it takes us to get around to that.

• 22:48Speaker 01

  Exactly, exactly. And, and sort of for Epictetus, he comes to terms with his condition of enslavement by going within and, and seeking freedom inside of him. And ultimately, this leads the Stoics to really not think about slavery all that much, right? Because, because they have sort of gone within and, and decided that inner mental freedom sort of obviates real, real life slavery in the world. But Diogenes does not make this step, right? And I think this is sort of the most powerful moment where you see that Diogenes is able to think outside of the status quo. And precisely because the world is not necessarily as it should be.

• 23:32Speaker 01

  There's, there's no reason why the status quo should be good. You don't have to revere it, right? You don't have to try to make sense of it as it is. You can say, no, actually, this is ridiculous. And, and that is what Diogenes does do centuries before anyone else. And more, more clearly and more, in a much more principled way to say that this notion of one human being owning another human being is completely absurd, right? And, and the Stoics, as much as they take from Diogenes, they don't take that.

• 24:08Ryan Holiday?

  Yeah, it's like, society needs the sort of freaks and hippies and artists and weirdos who question everything, a lot of which not shouldn't be questioned, but, but there are good answers to why. And then there's the bucket, the handful of things that it actually turns out that the reasons are pretty spurious.

• 24:27Speaker 01

  Yes.

• 24:28Ryan Holiday?

  And Diogenes, by effectively rejecting everything, is able to be right about this thing that, what's interesting too is like, as, I feel like the earlier Stoics are more cynical and more, more of the cynics school. And then by the time we get to Rome, now you have so many additional centuries of the status quo being the status quo, that it's harder for them to question. Like, like Cato thinks Rome is a republic. By the time it gets to Seneca, there's been so many bad emperors and so much civil war that he's just like this, like, let's just go with the most stable of the, you know? And, and by the time it gets to Marcus Aurelius, he's not like, like the idea in Gladiator

• 25:12Ryan Holiday?

  that he would give it up is so like, no, like, there is that lowercase c conservatism to the Stoics that the more transgressive radical early Stoics would not have conceived of.

• 25:26Speaker 01

  Yeah. And I mean, sort of a more socio-historical way of thinking about that is that sort of like as Stoicism becomes institutionalized and as Stoicism sort of seeps into the upper regions of society, the Stoics start to become people who have much more to lose. And, and, and at that point, it becomes much more difficult for them to, to sort of be as critical and as principled and as questioning as the cynics are.

• 25:54Ryan Holiday?

  What's fair, Upton's and Claire says it's very hard to get someone to understand something that their salary depends on them not understanding.

• 26:00Speaker 01

  Right.

• 26:00Ryan Holiday?

  And, and yeah, as it's like the feature and the bug, the Epicureans and the cynics are always on the outside so they can see things clearly. The Stoics slowly but surely get absorbed to not just be the inside, but kind of the dominant view of the elites in Rome. And so they have not just the, the, the sort of fear of change, but they also have, in some cases, good reasons, or not good, but just they just go, do you understand the cost, not like the literal cost, but I, it's like, that's easy for you to say, you don't have to make said decision, or you don't have, that's easy for you to say, let me tell you all the reasons why, you know?

• 26:41Ryan Holiday?

  And, and that is the, that's just the, they evolve further and further from each other to the point of being probably incomprehensible to each other.

• 26:50Speaker 01

  Right. Yeah. No, I mean, they, like Stoics become. So invested, they are insiders in a way. And from the inside, it can be really difficult to see. And if you are no longer communicating with people who are on the outside, then you've lost that that opportunity.

• 27:09Ryan Holiday?

  Yeah. The other one where there, I think the cynics are more right than the Stoics, or it takes a while, is, uh, Zeno is not just taught by Crates, but by Crates' wife. And there is an equality of the sexes to us. I mean, there's some misogynistic comments from Diogenes, but but there, there was a kind of equality in the lowliness of cynicism that it takes a while, takes maybe until Musonius Rufus, who also teaches, has these interesting essays on whether women should be taught philosophy. And he says, yes, but like, as Stoicism gets absorbed into the social hierarchy of Rome, certain questions are no longer asked and certain radical notions of equality go away.

• 27:50Speaker 01

  Yeah. Yeah. And what's interesting about this to me is that Diogenes himself does not explicitly really have an awful lot to say about women other than some off-color remarks, for sure. But it is then with the next generation, with Crates and his wife Hipparchia, that it becomes clear that there is, there's nothing about cynicism that precludes women from participating in it. And then it is Hipparchia who sort of takes up, like, seizes that opportunity. And then it becomes a feature of cynicism, precisely because to be a philosopher and to like, ask these questions, you do not have to have wealth.

• 28:34Speaker 01

  You do not have to be sort of a ruling member of your, of your polity, because philosophy has become this much more basic, day-to-day thing, as it is for Diogenes. And there is virtue in not having anything. And there's virtue in not participating in the polis as a political actor. So all of these things that sort of would preclude a woman from being a serious philosophical actor before

• 29:03Ryan Holiday?

  Yeah.

• 29:04Speaker 01

  are gone in Diogenes's thinking.

• 29:07Ryan Holiday?

  Right.

• 29:08Speaker 01

  Hipparchia and Crati sort of draw the natural conclusion from it, which was, which was there already at the start. It just wasn't realized in Diogenes's lifetime.

• 29:16Ryan Holiday?

  Yeah, he just personally didn't seem to care that much about it.

• 29:19Speaker 01

  Right, exactly, exactly. And then, once Hipparchia sort of joins the ranks of cynic philosophy, she becomes a figure who's quite popular in, in imperial cynicism and, and sort of is featured a lot in, in the Cynic Letters. And sort of her, like, her ownership of, of philosophy becomes, becomes important. And I do wonder if, you know, if that does not also influence Musonius Rufus, who is, you know, is a little bit of an outlier among the Stoics.

• 29:48Ryan Holiday?

  He's not a Roman senator in the way that these other Roman Stoics all seem to be, come from the best families and inherit power and status.

• 29:59Speaker 01

  Yeah, and then, and then Musonius sort of continues to think about this question. Like, well, why, why shouldn't women be studying philosophy?

• 30:07Ryan Holiday?

  Virtue is virtue. What does it have to do with your genitals?

• 30:09Speaker 01

  Yeah, exactly.

• 30:10Ryan Holiday?

  Nothing, yeah. And then also, here he is teaching probably the most cynic adjacent of the Stoics, right? Epictetus is the closest, I think, because also, he sees Rome from the outside and isn't part of the elite. So he is less, you know, he is more radical. He is more indifferent to the things that, you know, Marcus Aurelius is sleeping on a hard mattress by choice.

• 30:34Speaker 01

  Right.

• 30:34Ryan Holiday?

  Seneca is practicing poverty one day a month. And Epictetus is like, no, no, this isn't a game.

• 30:41Speaker 01

  Right.

• 30:41Ryan Holiday?

  This is life.

• 30:42Speaker 01

  Yeah, yeah. And also, I think, when you're reading Epictetus, you hear Diogenes a little bit more than a lot of the other Stoic writing. There's something about Epictetus's insistence, sharpness, wit. And, and also very much sort of the- Active, ongoing educational situation that you see in his writings, that he's always in conversation with someone.

• 31:08Ryan Holiday?

  Yes.

• 31:08Speaker 01

  That sort of feels-

• 31:08Ryan Holiday?

  Also not a writer, unlike Seneca or Marcus or these others.

• 31:11Speaker 01

  Exactly, exactly. That feels close to Diogenes.

• 31:14Ryan Holiday?

  And then we get the mirror of the Alexander and Diogenes when Hadrian, who's obsessed with Greece, stops in and attends Epictetus's lectures.

• 31:24Speaker 01

  Right.

• 31:24Ryan Holiday?

  And you're just like, again, some people are like, did it happen, did it not? And it's like, it probably did happen and it would make sense. And there's something that they probably both would have appreciated in the moment, the irony and the contrast between master and student. It's just a remarkable little scene.

• 31:42Speaker 01

  Yeah. Yeah. And I mean, I think for Hadrian, like all of Greek culture, all of the Greek world, what, you know, was entirely where his heart was.

• 31:52Ryan Holiday?

  Yes.

• 31:52Speaker 01

  And he was sort of invested in it from, from head to toe. So.

• 31:57Ryan Holiday?

  There's an element of it where it's like, you find out, like Paul Ryan's a Rage Against the Machine fan and you're like, you like it, but you obviously don't fucking get it.

• 32:05Speaker 01

  Right.

• 32:05Ryan Holiday?

  You know?

• 32:05Speaker 01

  Yeah.

• 32:06Ryan Holiday?

  And you're, there's something like Marcus really seems to have sincerely liked the philosophy. Hadrian seems to have really been a student of it, but like effectively puts zero of it into practice. It's like, he likes like the images and the symbols.

• 32:20Speaker 01

  Right.

• 32:20Ryan Holiday?

  But not any of the ideas.

• 32:23Speaker 01

  Yeah. Yeah. And I mean, I think also that for Marcus Aurelius, the, you know, the fact that we can read the meditations, but that it's so, you know, that they are not written as public facing documents.

• 32:38Ryan Holiday?

  Yeah.

• 32:38Speaker 01

  Right? I mean, we are really seeing him there in his private moments.

• 32:42Ryan Holiday?

  Yeah.

• 32:43Speaker 01

  So, so we see him struggling with these things in, like in an honest way that I think is believable and makes sense for, for a ruler. But in terms of, you know, would, would Diogenes say, you've really understood me, Marcus Aurelius? Maybe in some moments in the meditations, but not in his actions.

• 33:04Ryan Holiday?

  He would have stamped on his carpets.

• 33:05Speaker 01

  Right. Yeah, exactly, exactly. And, you know, Marcus Aurelius went on being Marcus Aurelius.

• 33:11Ryan Holiday?

  Yeah.

• 33:12Speaker 01

  And, you know, no matter sort of what he understood, as did Alexander, you know?

• 33:28Ryan Holiday?

  Why do you think the three words have been done such an injustice in the English language? Is it as true in other languages like stoic, epicurean, cynic? It's like they're not even in the ballpark of what they meant as philosophies.

• 33:42Speaker 01

  Yeah.

• 33:42Ryan Holiday?

  When and how does that happen?

• 33:45Speaker 01

  So I can speak specifically for cynics. And I, you know, I agree with you that all three words have sort of really suffered, but perhaps cynic, the worst, I would say, because it's such a negative word, right? It's like almost exclusively a negative word, cynic with a lowercase c. So when this happens is in the 18th, 19th century, like the late 18th, early 19th century. So up until that time, the word cynic in the vernacular European languages only means a cynic philosopher in the spirit of Diogenes.

• 34:22Ryan Holiday?

  Got it.

• 34:22Speaker 01

  Okay.

• 34:23Ryan Holiday?

  Like it means the philosopher, not an attribute of a person adjacent to the thing.

• 34:28Speaker 01

  Exactly, exactly. But like that, like that latter word does not yet exist.

• 34:33Ryan Holiday?

  The uppercase becomes the lowercase.

• 34:35Speaker 01

  Exactly, exactly. So at this time, the lowercase is introduced and the lowercase is introduced with reference to Rousseau. And what's really interesting about this is that Rousseau himself aligns himself to some extent with Diogenes. And Diogenes was a very popular figure in the French Enlightenment in general because he places such an emphasis on the human use of reason and is sort of so anti-authoritarian and anti sort of the traditional divisions in society, which is all very much at home in the French Enlightenment. So. Diogenes is a popular figure.

• 35:18Speaker 01

  Uppercase cynic is a positive term. It's about intellectual independence. Then the problem with Rousseau becomes that there is sort of a big mismatch between his philosophy and the way he lives his life.

• 35:32Ryan Holiday?

  Yeah, he's a shitty person.

• 35:33Speaker 01

  Yes. And he's not ashamed about being a shitty person.

• 35:36Ryan Holiday?

  Right. For people to know, he has like five kids and he just, one after another, gives them up for adoption, just doesn't want them.

• 35:42Speaker 01

  Yes, yeah.

• 35:42Ryan Holiday?

  Among other things.

• 35:43Speaker 01

  And he's very open about this. He's not embarrassed about this at all.

• 35:47Ryan Holiday?

  Do you think he's a sociopath or something? What do you think it is?

• 35:50Speaker 01

  Oh, I really don't know. I mean, I think maybe, like, when I think about Rousseau and sort of this problem is that he was, like, where Diogenes would say, yes, I've changed my mind, or, yes, this is not entirely, not entirely consistent with me, right? I think Rousseau was trying to make it all fit, right? And, and sort of that's where he becomes a hypocrite and somewhat crazy.

• 36:17Ryan Holiday?

  I was thinking about this. Rousseau is like, if Camus actually had murdered someone.

• 36:22Speaker 01

  Right.

• 36:22Ryan Holiday?

  You know what, like, if this stranger wasn't a novel?

• 36:25Speaker 01

  Right.

• 36:25Ryan Holiday?

  And he just murdered someone just to see what it was like.

• 36:28Speaker 01

  Right.

• 36:28Ryan Holiday?

  Rousseau has the elements of that.

• 36:30Speaker 01

  Yeah, yeah, absolutely. So it is in reference to Rousseau that this lowercase cynic word is invented, right? And sort of then comes to mean hypocritical or living your life as if there is no difference between good and bad.

• 36:51Ryan Holiday?

  Cynic becomes nihilist.

• 36:53Speaker 01

  Exactly.

• 36:54Ryan Holiday?

  Basically.

• 36:54Speaker 01

  Yeah, yeah, exactly. And, and, and sort of the notion that there are no standards of, of justice and that, that it doesn't matter, right? It's a very pessimistic worldview, which is the absolute opposite of what Diogenes thinks, right? Diogenes thinks that it is possible to be a good person and to live a good life. And he thinks that this is something that everybody can do and he wants to teach everybody about this.

• 37:20Ryan Holiday?

  But he's an idealist in a weird way.

• 37:21Speaker 01

  Yeah, yeah, yeah.

• 37:22Ryan Holiday?

  You know, they say like, a cynic is a spurned idealist. He's not spurned.

• 37:27Speaker 01

  Right.

• 37:27Ryan Holiday?

  He just believes it, and he believes it to these preposterous extremes, which he, for the most part, puts into practice.

• 37:34Speaker 01

  Yeah, exactly, exactly. And it is.

• 37:38Speaker 01

  It is the, it is the fact that he really believes this, right? That, that to my mind makes that he's absolutely not a lowercase cynic.

• 37:46Ryan Holiday?

  Yes.

• 37:46Speaker 01

  But, but I think he is sort of able to be an idealist because he does not pretend to be flawless.

• 37:54Ryan Holiday?

  Right.

• 37:54Speaker 01

  And there's this other anecdote, which I, which I really love, where he says, I'm sort of like a choir director. And I sort of give the pitch to the chorus, but I give it a little bit higher because I know that they will not quite be able to hit.

• 38:11Ryan Holiday?

  Right.

• 38:11Speaker 01

  The tone. So if they are sort of striving for what I'm seeing for them, they, they will get very far in the right direction. So, so that, so there is sort of this understanding that, you know, what, what he is doing is not systematic, is not perfect.

• 38:31Ryan Holiday?

  Yeah.

• 38:31Speaker 01

  He is, he is, he is setting a tone for us that we can sort of go towards. And I think it is precisely because of this acceptance of, of this impurity that you're protected against becoming a spurned idealist. Right? Because you were, you were never an absolutist idealist anyway, right? And being an absolutist idealist is, is so dangerous, you know, because it is, it is impossible. Right? And, and then once you get knocked down, once you sort of fall into the abyss, then, then what are you going to do? Right? Then you're sort of in this place where it's like, well, there's, it's not possible to do the right thing anyway. So why even bother? And, you know, none of it, none of it matters.

• 39:16Speaker 01

  That's, that's why you become a lowercase cynic.

• 39:18Ryan Holiday?

  Yeah. If Diogenes was a cynic in that sense, he wouldn't have spent all this time trying to teach people.

• 39:23Speaker 01

  Oh, absolutely.

• 39:23Ryan Holiday?

  He would have given up on them. Like, he doesn't like some of the people in Athens, but I would, he seems like he likes the people of Athens more than Socrates does. Do you know?

• 39:32Speaker 01

  Why, why would you say that?

• 39:33Ryan Holiday?

  I just mean like, well, first off, he manages to be transgressive and different and provocative and nobody kills him.

• 39:41Speaker 01

  Right?

• 39:41Ryan Holiday?

  You know, like, like in a way, Diogenes has better social skills than Socrates. Like, I can't get over the fact that Socrates goes on trial and, you know, like.

• 39:56Ryan Holiday?

  51% of the jurors vote to acquit him or vote to convict him. And then when he gives his speech at sentencing, like 55% vote to convict him to death. Like, he's so obnoxious that, you know, they say art is getting away with it. Diogenes, for the most part, gets away with it in a way that Socrates doesn't. And I think, just to go against this idea of being cynical and nasty and antisocial, I think the people of Athens, Schumer, Diogenes, there is more fondness than you might presume, or it wouldn't have allowed to go on.

• 40:35Speaker 01

  Right. Yeah, no, and I think that Diogenes's shamelessness and, and his give and take, as it were, right, are what sort of, there's, there's just something about the moment that allows you to, like, when you're in an exchange with Diogenes, right? Like, somebody comes up to him and says, and says, "Did you know that movement is not possible?" Right? And he's trying to sort of like, open this very theoretical, complex philosophical dilemma that people were excited about at the time. And Diogenes just gets up and walks a circle around him.

• 41:10Ryan Holiday?

  Here's your featherless biped.

• 41:12Speaker 01

  Right, exactly, exactly. And these moments are so absurd and disarming that they allow you to look at yourself and look at the world differently in that moment, in like, sort of a very performative, direct way. Whereas if you're in a conversation with Socrates, and you know, I fell in love with ancient philosophy because of Socrates, because of Plato, right? This is like, this is, these were my first, my first people, my first authors. But often, when you read a platonic dialogue where Socrates is questioning someone, it's like such, it's like such a slow burn.

• 41:49Ryan Holiday?

  Just say what you fucking mean, dude.

• 41:50Speaker 01

  Like, he, like, he makes you think that you're doing so well. He makes you think that you're like, on to something, and he's like... Oh, really? Oh, really? Well, let's go to the next step. And then only at the very, very end is like, oh, wait a second. Everything of what I just said is nonsense. And we're only finding out now.

• 42:11Ryan Holiday?

  Well, I think there's, in a way, this is an extreme position, but I, there's something kind of intellectually dishonest about the Socratic method, right? Like, he's able, he knows what he thinks, but he never has to say it. He just relentlessly questions you until you question what you thought. And then his implication hangs there.

• 42:30Speaker 01

  Yeah.

• 42:30Ryan Holiday?

  Right? And I think there's something refreshing about Diogenes, who just says what he means in a clever, straightforward way.

• 42:39Speaker 01

  Yeah.

• 42:39Ryan Holiday?

  From the jump.

• 42:40Speaker 01

  Yeah, exactly, exactly. It's very direct.

• 42:43Ryan Holiday?

  Yeah.

• 42:44Speaker 01

  And transparent and, and quick. And it's, you know, it's, it's a performance. It's, it's a moment.

• 42:49Ryan Holiday?

  It's like a punk song.

• 42:50Speaker 01

  Yeah, it's a moment. It's a punk song that you can share.

• 42:53Ryan Holiday?

  Yeah.

• 42:53Speaker 01

  And then you are altered. And I see, I'm, you know, I'm going to be like very nuanced here. Like, I think that the Socratic method is amazing, precisely because it takes you through your own arguments and, and, and sort of you go step by step and you sort of get there yourself, right? And I do think that that's beautiful and that's really important. It's just that when we read-

• 43:18Ryan Holiday?

  Being interrogated by Socrates, though, is different.

• 43:21Speaker 01

  Oh, exactly, exactly. And, and also, like, when we read Plato's account of these, of these interrogations, which of course, you know, are written after the fact and, you know, are, are scripted in a certain way. It's, you know, it's just so clear and it just makes the interlocutor look so bad. And it makes, you know, and I agree with you that there are many moments where it does feel like Socrates is being dishonest. Like, you clearly know where this is going. Like, what, like, why does it have to be? Why does it have to be like this?

• 43:54Ryan Holiday?

  Yeah, I think it was Macaulay who said, "The more I read about Socrates, the more I understand why they killed him." And, and, uh, yeah, I just, Diogenes gets away with it. You know, and, and, uh, that's an impressive feat, I think.

• 44:06Speaker 01

  Absolutely, yeah.

• 44:07Ryan Holiday?

  Well, I think the book is amazing and I think more people should know who he is. So thank you for writing it.

• 44:12Speaker 01

  Thank you so much for, for talking with me about it.

• 44:14Ryan Holiday?

  You want to check out some books real fast?

• 44:16Speaker 01

  Uh, yeah, let's do that.

• 44:17Ryan Holiday?

  All right, let's do it.

• 44:20Ryan Holiday?

  Ooh, okay, so do you know about Ambrose Bierce? The American cynic?

• 44:24Speaker 01

  No.

• 44:25Ryan Holiday?

  He's like our most famous cynic.

• 44:27Speaker 01

  Oh, God.

• 44:28Ryan Holiday?

  Uh, so, okay, so he's, he wrote The Devil's Dictionary. He's known famously as the cynic.

• 44:33Speaker 01

  Uh huh.

• 44:33Ryan Holiday?

  Um, he fights in the, for the Union in the Civil War.

• 44:37Speaker 01

  Yeah.

• 44:37Ryan Holiday?

  And he writes this famous story called, uh, An Occurrence at Owl Creek Bridge, which is probably the most famous, have you heard of this short story?

• 44:44Speaker 01

  No.

• 44:45Ryan Holiday?

  It's like an amazing short story. It's like super good. So he, and then he becomes like this sort of muckraking journalist in the Gilded Age. He's like contemporary with Mark Twain and stuff. And so everyone, he's like lowercase cynic because he's calling out all the bullshit and the horrors of his time. But like people aren't getting like, uh, Diogenes, he's this idealist at heart. He's like, I don't understand why we're letting these railroad barons buy our democracy.

• 45:13Speaker 01

  Right, yeah.

• 45:13Ryan Holiday?

  And he's this fascinating guy. I think you're...

• 45:15Speaker 01

  Oh, I'm so excited. Thank you.

• 45:17Ryan Holiday?

  And then so the crazy sort of irony of it is he's actually, uh, Stoic. Like his, his father's name is Marcus Aurelius Bierce.

• 45:25Speaker 01

  Yes.

• 45:26Ryan Holiday?

  And his, uh, uncle, who's also, so it was a Civil War general, is named Lucius Verus Bierce.

• 45:31Speaker 01

  Oh, my God, that's amazing.

• 45:32Ryan Holiday?

  So he's kind of steeped in this classical tradition. And he's more, I, I don't, I haven't looked that much at what he's said about Diogenes. But he's, he has this Devil's Dictionary, which has all of these like hilarious things. Like, let me give you his, uh, let me give you his definition of a philosopher. It's so, the phrasing is good. I don't want to do it.

• 45:47Speaker 01

  Okay.

• 45:47Ryan Holiday?

  Ambrose Bierce.

• 45:49Speaker 01

  I had no idea that this...

• 45:50Ryan Holiday?

  You've never even heard of him?

• 45:51Speaker 01

  No, I had no idea this guy existed. I am so excited. Um, this is what I'll be bringing on a plane. It's amazing.

• 45:58Ryan Holiday?

  Uh, and the stories are like, there's not a great biography of him. Carrie McWilliams, who was like a sort of muckraking journalist in the 1900s, wrote a biography about him, but it's very out of print.

• 46:10Speaker 01

  Mm-hmm.

• 46:11Ryan Holiday?

  Um, so his definite, so The Devil's Dictionary is his most famous work because most of his journalism, other than this one short story, is all forgotten.

• 46:17Speaker 01

  Yeah.

• 46:18Ryan Holiday?

  But, um, he, uh, his definition of a philosopher is, "All are lunatics, but he who can analyze his delusion is called a philosopher."

• 46:28Speaker 01

  That's excellent.

• 46:29Ryan Holiday?

  So that one's good. And then the two stories I would read. So he has, um, okay, so, yeah, Occurrence of Alcridge, start there. And then, um, read a Parker Atterson philosopher.

• 46:41Speaker 01

  Okay.

• 46:41Ryan Holiday?

  Which is this short story about this Union soldier who's caught as a spy.

• 46:45Speaker 01

  Uh huh.

• 46:46Ryan Holiday?

  And he is like being interrogated and he's this brave sort of prisoner.

• 46:51Speaker 01

  Yeah.

• 46:51Ryan Holiday?

  Um, and he's, he's, he's aping all the things that a stoic or a cynic would say.

• 46:57Speaker 01

  Yeah.

• 46:57Ryan Holiday?

  If they're about to be a sentence to death, which he knows is his thing.

• 47:02Speaker 01

  Yes.

• 47:02Ryan Holiday?

  And then like at the last second, and all of his things have a twist, so I won't. But at the last second, they tell him, oh, you're not going to be executed by firing squad. You're a spy, you're going to be hung. And then we see whether he means the philosophical pretensions or not.

• 47:17Speaker 01

  Yes.

• 47:17Ryan Holiday?

  So he's, I think you'll really like him.

• 47:19Speaker 01

  Yeah.

• 47:20Ryan Holiday?

  Okay, um, what else might you like? What do you think like the best edition of, like, if someone was like, I want to read Diogenes, other than your biography, I would, because we've been trying to round out the philosophy. I think I read the Penguin collection of passages, but what do you recommend to people?

• 47:36Speaker 01

  I, I mean, I think the, uh, I think the Penguin edition, uh, by Robin Hart is really good because it's quite complete and it has sort of, like, has basically everything you need.

• 47:49Ryan Holiday?

  Okay.

• 47:50Speaker 01

  In, um, in English, um, there's also, um, in this series, in this Princeton series, there is a recent one.

• 47:59Ryan Holiday?

  Is there one of Diogenes?

• 48:00Speaker 01

  Yes.

• 48:01Ryan Holiday?

  Okay.

• 48:01Speaker 01

  Yeah, yeah, yeah.

• 48:02Ryan Holiday?

  I'll, I'll make sure to get this.

• 48:02Speaker 01

  Um, and I think it's called How to Say No.

• 48:04Ryan Holiday?

  How to Say No, okay. This series is incredible.

• 48:07Speaker 01

  No, it's a great series, yeah.

• 48:09Ryan Holiday?

  I think doing, I don't know why it's also in Latin. I, I think it would be more accessible if it was just.

• 48:14Speaker 01

  Oh, I was just, I was just going to say, I think it's so nice that they're bilingual because, you know, maybe it'll tempt people, um.

• 48:21Ryan Holiday?

  Yeah, maybe, sure.

• 48:22Speaker 01

  Into, uh, into seeing if they can read some of those on their own.

• 48:26Ryan Holiday?

  Yeah, sure.

• 48:27Speaker 01

  Yeah, yeah, yeah. So, yeah, How to Say No is, is the Princeton one.

• 48:30Ryan Holiday?

  All right, we'll carry that one.

• 48:30Speaker 01

  About Diogenes, um, which I think, which I think is great.

• 48:34Ryan Holiday?

  Okay, all right.

• 48:35Speaker 01

  Yeah.

• 48:35Ryan Holiday?

  Um, yeah, he's sort of like, uh, like Musonius Rufus, where there's just not a great, have you read this?

• 48:41Speaker 01

  Yeah, yeah, I mean, I think, I think her translation.

• 48:43Ryan Holiday?

  I thought it was really good, yeah.

• 48:45Speaker 01

  It's what I give to my students.

• 48:46Ryan Holiday?

  I, the title is not good.

• 48:49Speaker 01

  Right, yeah.

• 48:50Ryan Holiday?

  It's almost as bad as like cynic or stoic where you're like, wait, so, okay. Like, cause it's, it so comes down to the words, right? It's like that one should disdain hardships. To me, it sounds like it's saying like, avoid hardships.

• 49:02Speaker 01

  Exactly.

• 49:02Ryan Holiday?

  In the same way that like, uh, like apathy or resignation or, um, uh, indifference are these words that like mean the opposite of what?

• 49:12Speaker 01

  No, and it's exactly like also a same word, uh, or similar thing with scorn. With students, like I always talk about scorn, like what do they mean you should scorn it? Well, what it means is that you shouldn't allow yourself to be bothered by it, but you shouldn't avoid it. Right? You should be ready for it.

• 49:28Ryan Holiday?

  Yes.

• 49:29Speaker 01

  If, if you encounter it, then you have to, you know, not be, uh, derailed, right? That is what it means. But, but yeah, I mean, those words are used.

• 49:38Ryan Holiday?

  Are these things better in other languages? Like, like how does Dutch render the, is, is it, are there similar problems or it's like, no, no, no, cause our word is, you know, like bazillion consonants and then?

• 49:49Speaker 01

  There's, there's similar problems. Yeah. I mean, there's, you know, the only thing that, um, that I really like about German is that they actually came up with two different words for modern cynicism.

• 50:01Ryan Holiday?

  Oh, really?

• 50:01Speaker 01

  And for ancient cynicism where, um, modern cynicism is cynismus with a Z, um, and then ancient cynicism is kenismus with a K.

• 50:11Ryan Holiday?

  See, that's brilliant.

• 50:12Speaker 01

  So that is really, really helpful. So helpful. I wish we did that in other languages, but not in Dutch.

• 50:17Ryan Holiday?

  When the Germans also would be like, well, why don't we just mash like 15 words together and call that a new word?

• 50:22Speaker 01

  Yes. They like to do that too. But we, we like to do that in Dutch a little bit as well.

• 50:26Ryan Holiday?

  Yeah.

• 50:27Speaker 01

  There's a lot of words for sure.

• 50:29Ryan Holiday?

  We don't do that in English very much.

• 50:31Speaker 01

  No, no, everything's its own little word.

• 50:32Ryan Holiday?

  I know. Um, but the nuance of it is interesting. Have you read, uh, just now I'm writing about it now. Have you read any of Stockdale?

• 50:40Speaker 01

  I have not.

• 50:40Ryan Holiday?

  Do you know who that is?

• 50:42Speaker 01

  Um.

• 50:42Ryan Holiday?

  So Stockdale's, uh, maybe this, this book I think is really interesting.

• 50:46Speaker 01

  Yeah. No, I've definitely, I've definitely, um, I know his story, but I haven't read him.

• 50:50Ryan Holiday?

  It's, it's more, it's more overtly philosophical than you would think. Like, so as he's parachuting in, he says like, he knows he's gonna, he's like, I'm entering the world of Epictetus. Like he's explicitly thinking of a POW camp as a training ground to be a philosopher.

• 51:09Speaker 01

  Yeah.

• 51:10Ryan Holiday?

  Which is heavy and very interesting.

• 51:12Speaker 01

  Yeah. And also so, so true to the Stoics and the cynics.

• 51:17Ryan Holiday?

  Yes.

• 51:18Speaker 01

  To, to sort of say, okay. This is what I'm experiencing. This is happening to me right now and this is what I've trained for. And I'm ready for it and it's an opportunity to sort of, um, to develop myself even further and it's.

• 51:34Ryan Holiday?

  But also the idea that the philosophers are not having easy tenured lives.

• 51:40Speaker 01

  Oh, yeah, no, absolutely.

• 51:41Ryan Holiday?

  In the sense of like, like even Diogenes, you're like, oh, but it's like, he's living thousands of miles from, or I don't know, hundreds of miles, how far is it exactly? But he, like exile must not have been fun. Like he might have made a light of it, but he's sent away from where he, and he loses everything, you know? Like there, there is this sense of, like, I love this, they did a new edition of Viktor Frankl and it's, uh, yes to life. And then the subtitle is in spite of everything. There's something about that of the ancient Stoics are just having a rough go at it that I think is powerful.

• 52:14Speaker 01

  Yeah, and also the very basic, I mean, it almost sounds like a platitude, but I do think it's so meaningful to say that philosophy is something that you live. Right? It's, it's, it's something that's in your experience and it is in the everyday and it is in the very smallest thing. And like in your very smallest position and it's, it's not an armchair activity.

• 52:40Ryan Holiday?

  Well, I think that's probably why Diogenes was so dismissive of that, like the thing about like, what's a human? It's a featherless biped or the, the like, oh, we can't walk or you can't move. And it's like, let me show you. He's just like, I don't have time for this bullshit. Let me, like, they, these are not the questions we should be asking. The questions are not like, how do we know if we live in a computer simulation? It's like, what am I supposed to do about the fact that the government just took my stuff and threw me in jail?

• 53:07Speaker 01

  Yeah, yeah. No, and, and especially if you're sort of pursuing all of these hyper theoretical abstract questions. But in your everyday life are sort of being very unreflective and very unethical. Like, I mean, that, like, that is what gets Diogenes mad, right? And then she gets all this mad.

• 53:29Ryan Holiday?

  Actually working for Alexander.

• 53:32Speaker 01

  Oh, I mean, I think, you know, I think he, he thought just as, as badly of it as he thought of, of Plato going to Sisae. Right? I think he would have had no, no respect, right?

• 53:45Ryan Holiday?

  James Rahm was actually just here.

• 53:47Speaker 01

  Yeah, I saw, I saw.

• 53:48Ryan Holiday?

  His book about, um, what's the tyrant's name?

• 53:51Speaker 01

  Dionysus, yeah, yeah, yeah.

• 53:53Ryan Holiday?

  Is fascinating, that they would both, because his book about Seneca, I love, that, that two smart people would get snookered so badly. By something that like, and I guess this goes to your point about being on the outside of the inside, that is so trans, was so transparently obvious to everyone else who thought about. And then you're like, oh yeah, there's all the, like you see it now, these smart people who, who like, there's obviously dumb people who fall for demagogues, right? All the time, that's what a demagogue does. But what's more interesting than, of course, terrifying, is the mental gymnastics that a smart person can do. To be like, actually, this isn't horrible and it's good and that's why I should participate.

• 54:36Speaker 01

  Yeah, yeah, exactly. And, and I mean, I think it's, I think it's a combination between, you know, wanting, wanting to be part of, of the moment, right? And sort of being misguided about what you're, what you're best, exactly, wanting to be in the room where it happens, right? And being misguided about, um, the trade-off between impact and also being misguided about what impact is, right? I mean, Dionysus goes into the marketplace because he thinks that's where it can have impact, because that's where everybody will see him and, and, and talk to him. And he does, um, and yeah, I mean, yeah, I think it's a combination between wanting to be in the room where it happens.

• 55:16Speaker 01

  And sort of, you know, being sensitive to status, being sensitive to status of the king and being like, well, if the king wants me to come.

• 55:25Ryan Holiday?

  And also that the superpower of kings, it's the brutality often, and the violence, and the power. But also they're really good at provoking that reaction in people. Like, like they're really good at making you think that you're important to them and that they need you. And that you can. restrain them and

• 55:48Speaker 01

  yes

• 55:48Ryan Holiday?

  you know like they're they're the superpower is eh like the superpower of a trump is his ability for every person to meet him and go oh it's gonna go differently with me and you like that Elon Musk is gonna be like no I think it's gonna go well it's like anyone with like so what is that ability and I think that's what's what what both Plato and Nero fall for and Diogenes has no like

• 56:15Speaker 01

  no

• 56:15Ryan Holiday?

  doesn't entertain it for a second

• 56:17Speaker 01

  yeah

• 56:17Ryan Holiday?

  he sees Alexander

• 56:19Speaker 01

  exactly

• 56:19Ryan Holiday?

  for what he is

• 56:20Speaker 01

  yeah no and I think you know for Diogenes he meets Alexander and if if Alexander had wanted to change his life

• 56:29Ryan Holiday?

  yeah

• 56:29Speaker 01

  after he met Diogenes great

• 56:31Ryan Holiday?

  yeah

• 56:31Speaker 01

  right but Diogenes was not going to go to Alexander and was not going to change himself and drop everything because he thinks he's the one and because he thinks well ooh it's Alexander I mean he was ultimately just not intimidated by Alexander he was like okay Alexander is just the same as the fishmonger I talked to yesterday and if Alexander wants to talk to me that's just as interesting as talking to the fishmonger that's great um

• 57:01Ryan Holiday?

  but he's also probably like he's a psychopath I I think probably reads I I bet he I bet he sees him clearly as unchangeable in a way that Aristotle fools himself

• 57:12Speaker 01

  right

• 57:13Ryan Holiday?

  about

• 57:13Speaker 01

  yeah

• 57:14Ryan Holiday?

  you know

• 57:14Speaker 01

  yeah

• 57:15Ryan Holiday?

  that he would listen

• 57:16Speaker 01

  yeah no and and also you know for for Diogenes he I mean he he sets the terms

• 57:24Ryan Holiday?

  yes

• 57:24Speaker 01

  right like so so okay if if there was maybe some hope for Alexander the very first step is that he comes to him instead of expecting Diogenes to go there right so it's already in that motion that you see the big difference between Diogenes and everyone else that he won't go and visit him

• 57:43Ryan Holiday?

  yeah I have a quote that I keep next to my desk where it's soft and I think they were Pompey's last words it's a line from Softcase he says whoever goes to the court of a tyrant becomes his slave even if he goes there a free man

• 58:01Ryan 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.