The Philosopher Who Didn’t Care What Anyone Thought

The most fearless philosopher in the ancient world didn’t rule an empire or write books. He lived on the street and begged for food. And yet, he was bold enough to challenge Alexander the Great to his face. In today’s episode, we’re talking about Diogenes, the philosopher who rejected status, comfort, and approval and may have understood freedom better than anyone who came after him.🎥 Watch this episode on The Daily Stoic YouTube Channel: https://www.youtube.com/watch?v=m1JF8heGB2s🎙️ 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.

• 0:00Ryan Holiday?

  Welcome to the Daily Stoic Podcast, designed to help bring those four key Stoic virtues, courage, discipline, justice, and wisdom into the real world.

• 0:14Ryan Holiday?

  Do you know who the most brilliant, the most badass, the most powerful philosopher in the ancient world was? Because it wasn't Marcus Aurelius, the Emperor of Rome. It wasn't Socrates. It wasn't Plato. It wasn't Aristotle. It was a man who lived on the streets. It was a man who begged for his food. Yet it was this poor homeless man who could challenge Alexander the Great to his face, who could walk into Plato's house and stamp on his carpets. And yet, even though he didn't write basically anything down, had an enormous philosophical legacy. Stoicism as a philosophy would not exist without this man. And in today's video, that's who we're going to talk about. We're going to talk about Diogenes the Cynic.

• 0:58Ryan Holiday?

  We're going to talk about the school of philosophy known as cynicism. And we're going to talk about some lessons that the cynics can teach us to apply here in our very modern lives.

• 1:12Ryan Holiday?

  Now, you might have heard the word cynic before, like with a lowercase. And maybe you think that that's negative, right? That's someone who makes fun of stuff, who's pessimistic, who doesn't believe in anything. But just as Stoicism is not lowercase stoic, you know, has no emotions, has no feeling, totally invulnerable. That's not what the school of cynicism is as a philosophy either. The cynics actually, like the Stoics, tried to live in accordance with nature. Yes, they actively rejected some normal social conventions, materialism. They didn't care about superficial stuff. They were in favor of self-sufficiency and virtue. But they were also known for taking these ideas to the extreme.

• 1:56Ryan Holiday?

  There are stories about them that are kind of punk, right? They're like nude in public. They're using the bathroom wherever they want. They are testing and questioning things that other people are afraid to do. And actually, this was Something I talked about with the philosopher and Harvard professor Arthur Brooks about when he was on the Daily Stoic Podcast.

• 2:16Speaker 01

  To begin with, we don't understand them because we cast aspersions of people who are cynical.

• 2:22Ryan Holiday?

  Yes.

• 2:22Speaker 01

  I mean, the whole idea of the skeptics and the cynics, different schools, of course.

• 2:26Ryan Holiday?

  Yes.

• 2:26Speaker 01

  That there's something that's kind of suspect about their character. You know, you don't want to be a cynical person because you're just negative all the time. And that's exactly getting it wrong.

• 2:35Ryan Holiday?

  Yes.

• 2:35Speaker 01

  How do you characterize this school of cynicism?

• 2:38Ryan Holiday?

  I say they're like the punk rockers of the philosopher world. They are transgressive and radical by taking it too far, actually providing us insights about sort of a moderate middle ground. Like, if everyone lived as Diogenes lived, the world would be a horrible place. But if everyone lived as, according to ambition and trying to, you know, make as much money and get as much power and valued all the wrong things, you also get a really bad society.

• 3:06Speaker 01

  Right.

• 3:06Ryan Holiday?

  He's like the hippie sort of going, "None of this matters, man." You know, like, and doing gets a certain...

• 3:10Speaker 01

  Not even that, not even saying none of it matters. He's saying, "This is stupid."

• 3:13Ryan Holiday?

  Yes.

• 3:13Speaker 01

  So it's worse than whatevs.

• 3:15Ryan Holiday?

  Yeah. He's making fun of your suit.

• 3:17Speaker 01

  Yeah.

• 3:18Ryan Holiday?

  And your tie and your fancy car. I mean, the famous story about Diogenes that I love is, you know, he has very few possessions, but he walks up to the well, he gets a cup of water. A young boy runs up and gets water with his hands. And Diogenes realizes that even here, having reduced what he thought his needs were to nothing, actually has one more that he can get rid of and he smashes his cup on the ground.

• 3:40Speaker 01

  The cynics are interesting because what they do is they can make you realize that life is hilarious.

• 3:46Ryan Holiday?

  So Diogenes is probably the most well-known and the most extreme of the cynics. He's actually known as Diogenes the Dog because he lived in a barrel on the street in Athens. He tried not even to have clothes. But he wasn't always like this. Like all the great philosophers, there's an origin story. How does he go from his ordinary life to what he's known for? And this is something I talked to Professor Inger Kuhn about. She's a professor of classics at the University of Virginia. So for people who aren't familiar with him at all, let's start where he starts. How does he end up as a philosopher in Athens? He's in exile, right?

• 4:24Speaker 02

  Yes, that's right. Diogenes is born and...

• 4:28Speaker 02

  Probably a pretty well-to-do family in a town that's called Sinope, and it's on the coast of the Black Sea, and today it's in Turkey. At a certain point, either just him or him and his father get exiled from Sinope. So they have to leave. They cannot live there anymore, most likely because there was some problem with the coinage, with the mint. So Diogenes's dad was in charge of the mint, and there was some irregularity that led to them having to leave. He gets exiled, which means he loses his citizen rights in that place, and ends up in Athens, which to him ends up being really exciting.

• 5:13Speaker 02

  A few times, he says, like, well, the Sinopeans might have convicted me to exile, but they have convicted themselves to staying in Sinope, so I'm not all that bad. In Athens, he meets Antisthenes, who was a student of Socrates, and who sort of sets him, most likely, on the path of philosophy.

• 5:32Ryan Holiday?

  This is right after the death of Socrates?

• 5:35Speaker 02

  Yes. Yeah, yeah, yeah. So a few decades after the death of Socrates, which is still very reverberating for people.

• 5:43Ryan Holiday?

  And this philosophy thing is kind of new. Like, not, obviously, we go, there's the pre-Socratics and then the post-Socratics, but it's like, it's still up for grabs what this philosophy thing is going to be and mean to the Western world, because it's all being figured out just then.

• 6:03Speaker 02

  Yeah, I mean, it's a very vibrant time for it. And if we think about ancient wisdom and people trying to figure out how the world works, if there are gods, what they are like. I mean, this is something that people have been doing for at least two centuries already at this point. But at this time, 4th century BCE in Athens, there is a very vibrant competition over what philosophy should be, what it should be like, what kind of questions should be pursued, and in what way they should be pursued. So in that sense, it is a perfect time for Diogenes to show up there.

• 6:44Ryan Holiday?

  And then Diogenes is right there in the middle of the reign of Alexander the Great, who's in the middle of gobbling up the world.

• 7:03Ryan Holiday?

  Diogenes believed that there was corruption, there was lies, that people were being sold a bill of goods. And I think he believes that his job is to point out this hypocrisy, to call it out. You know, there's a story about him walking into a crowded theater backwards. And people go, "Why are you walking backwards?" And they start to laugh at him. And he says, "You're laughing at me for walking backwards, even though you've been walking in the wrong direction your whole life." There's another story about Diogenes. He's walking through Athens and he sees a thief arrested from the temple. And he's being led out of the temple by the priests. He says, "Oh, look, the big thieves are leading away the little thieves."

• 7:42Ryan Holiday?

  And here he is, calling out the hypocrisy, the greed of the religion of his time. He's kind of questioning everything. He's calling it all out. And this is what makes him such a provocative thinker and such a provocative thing to read, you know, even 2,500 years later. And Diogenes took his training really seriously. We're told that in the summer, he used to roll around in hot sand. And in the winter, he would embrace statues. Imagine a stone or a bronze statue that's freezing cold or even covered in snow. We're told he was trying to enure himself to hardship. He's trying to toughen himself up to figure out what he's capable of.

• 8:27Ryan Holiday?

  And you can imagine seeking out discomfort so that the discomforts of ordinary life are comfortable to him. There's another story about Diogenes when there's someone he wanted to learn from, another philosopher named Antisthenes. But apparently, Antisthenes was not interested in teaching Diogenes. And when Diogenes kept asking, "Will you teach me? Will you teach me?" The teacher raises his hand as if to strike Diogenes, to send him away. But Diogenes says, "Go ahead, hit me. There isn't wood hard enough that's going to keep me away from learning from you." Diogenes supposedly practices being rejected too, or practices the indifference of... Of other people were told he was once seen begging in front of a statue.

• 9:10Ryan Holiday?

  And by that, I mean literally begging the statue, which of course could not respond. He wanted to get used to the crickets, right? To having his request ignored entirely. And this idea of rejecting the favors and important people is actually a source of disagreement that Diogenes has with Plato. We're told Diogenes was seen washing some cabbages one day. And Plato says, you know, if you had come to Dionysus's court, served this tyrant that Plato had worked for, you wouldn't have to do that. And Diogenes looks at him and says, you know, if you just washed your cabbages, you wouldn't have had to go to Dionysus's court. And Diogenes was totally right because Plato had degraded himself in the service of this

• 9:55Ryan Holiday?

  man and was fooling himself about it. And Diogenes saw right through this. Diogenes was once asked what the most beautiful thing in the world was, and he said it was freedom of speech. He wasn't afraid to offend people. He wasn't afraid to question convention. He wasn't afraid to say what he thought was true, even if others thought it was weird, even if others disagreed, even if others thought it was inappropriate or uncouth. He said what he wanted to say, and that's the kind of freedom he was trying to cultivate. So in Athens, Diogenes is living on the streets, but this also puts him in a position to bump into some of the most influential people of his time, right? Athens is the center of the world. There's actually a famous story of Diogenes and Alexander the Great.

• 10:38Ryan Holiday?

  He's lying on a rock or in the road somewhere, just sunbathing. And Alexander the Great comes up to him. And Alexander the Great's a fan. And he says, you know, I'm Alexander the Great. Is there anything that I can do for you? And Diogenes looks at him and says, yeah, you can get out of my son, right? His request for the most powerful man in the world, a man who has conquered enormous swaths of territory, is to just get out of his way. So in this, I think there's a very Stoic idea of what power is, right? Do you have power over yourself or are you dependent on other people? There's something here about not needing Anything from anyone, right? Seneca talked about how poverty isn't the person who has little.

• 11:23Ryan Holiday?

  It's the person who wants more. There's obviously a lot of people in Greece that wanted something from Alexander the Great, that were dependent on him, or that thought of power as what they could get, not power as reducing what they needed. This idea from Seneca may actually have come from the Cynics, as Inger and I talked about.

• 11:42Speaker 02

  I mean, essentially, what happens is that Zeno founds his own school.

• 11:47Ryan Holiday?

  Yeah.

• 11:47Speaker 02

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

• 12:03Ryan Holiday?

  Okay.

• 12:03Speaker 02

  Where the Stoics were quite invested in distinguishing themselves from the Cynics.

• 12:10Ryan Holiday?

  Yeah.

• 12:10Speaker 02

  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. 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 living a contemplative life of philosophy is a forebear that the Stoics do want, which means that they have to accept the genealogy from Socrates to Antysinnes to Diogenes to Crates to Zeno.

• 12:44Ryan Holiday?

  Got it.

• 12:45Speaker 02

  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 in a historical sense, it's clear that...

• 12:55Ryan Holiday?

  One descends from the other.

• 12:56Speaker 02

  Exactly, exactly. 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 of Crates. So that all sort of works just fine from a historical perspective. Then, in addition to sort of needing this distance, there's also...

• 13:18Speaker 02

  Pretty fundamental differences philosophically. 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.

• 13:40Ryan Holiday?

  Right.

• 13:41Speaker 02

  So to put it a little bit in a banal way. The thing to do is to understand this organization and then to bring yourself, bring your inner self in line with this organization. Now, for the cynics, there is no such overarching organizing principle. 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.

• 14:07Ryan Holiday?

  Right.

• 14:07Speaker 02

  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. They admired the natural world. They admired the fact that the sun warms us, that we can drink water from the river, 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 we can live a good life.

• 14:35Ryan Holiday?

  Yeah.

• 14:35Speaker 02

  With what nature has given us.

• 14:37Ryan Holiday?

  Living in accordance with nature.

• 14:38Speaker 02

  Yeah, exactly, exactly. But beyond that, there's nothing about this world that's necessary.

• 14:44Ryan Holiday?

  Right.

• 14:44Speaker 02

  So when it comes to the social structures, the city that we live in, sort of the 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 has a lot of downstream consequences in terms of how Diogenes thinks about kingship and how he thinks about rulership.

• 15:09Ryan Holiday?

  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.

• 15:31Speaker 02

  Exactly. The society that we live in, the status quo is not God given, is not.

• 15:37Ryan Holiday?

  That's not part of nature.

• 15:38Speaker 02

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

• 15:44Ryan Holiday?

  Right.

• 15:44Speaker 02

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

• 15:47Ryan Holiday?

  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?

• 15:53Speaker 02

  Yeah.

• 15:53Ryan Holiday?

  Uh, although she's obviously coming out of 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. 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.

• 16:24Speaker 02

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

• 16:31Ryan Holiday?

  Yes.

• 16:31Speaker 02

  Right? In order to adjust to it and in order to sort of lead the most virtuous and dutiful life within that context, within your station, within the city that you live in. Whereas for cynics, we're questioning it to see if maybe there might be a better way to live.

• 16:47Ryan Holiday?

  With the Stoic school descending from the cynic school, there's, there's obviously a lot of overlap. There's a, a big similarity between the two schools. I think the big place they overlap is this idea of, of freedom. Freedom, not in the legal sense, but freedom from the things that enslave most of us. Diogenes talked about people being slaves three times over. He meant sex or gluttony or sleep. Seneca, coming a couple hundred years after Diogenes, talked about, he says, show me somebody who isn't a slave. He was talking about powerful people who are slaves to ambition, to their mistresses, to a compulsion, to money, to fear, to work, whatever it is.

• 17:30Ryan Holiday?

  And so they might have been on paper, much more powerful than someone like Diogenes or Epictetus. But if you actually look at their lives. Their day to day existence, they're actually not in control. They are actually powerless. Seneca would talk about this one Roman general. He says, you know, he commanded armies, but ambition commanded him. And so we come back to this, you know, idea of Diogenes. Who's more powerful, Diogenes or Alexander the Great? Now, of course, the cynics go a lot further than the Stoics in terms of achieving this freedom, getting rid of almost everything they own, reducing their desires to nothing. I don't know how practical or realistic that is for most of us, but I think there still is a lesson here that basically the more you want,

• 18:15Ryan Holiday?

  the more you need, the more you are vulnerable, the more you are not under your own power. And this is not just true for, you know, sort of material things, but also desires and urges and passions. Now, another crossover between the Stoics and the cynics is this idea of treating the body rigorously. Now, we might think of Diogenes sort of living on the streets as some kind of weakling, but he's kind of seeing this as like an athletic feat. Like, how little does he need? How tough can he be? How exposed can he be to the elements? What can he endure? And so for Diogenes, he's thinking about training and pushing the body. And in pushing the body, also pushing the mind and vice versa.

• 18:59Ryan Holiday?

  He saw that health and strength are both essential for the philosopher. You know, today we think of philosophers as sort of sitting in an ivory tower, in a cushy office, being a bit soft. But Diogenes was a hard guy who lived a hard life. And again, I think we can see a connection between the Stoics and the cynics via Seneca. Seneca said, "We treat the body rigorously so that it is not disobedient to the mind." The Stoics are saying you push yourself. You find out where your limits are. You develop strength and self-confidence. And independence is as a result of pushing yourself in this way. And not only does this make you healthier, it helps you think more clearly.

• 19:43Ryan Holiday?

  It makes you more resilient and it makes you ultimately better. Diographer of Diogenes, also named Diogenes. It's a little confusing. But he says, sure, we have the ideals. And that's what part of the philosophical training is about, the ideas. He says, but none of this, the ideas and the virtue, he says, none of it is complete without health, because health and strength are equally essential for training both the mind and the body. There's another story that I like about Diogenes. Diogenes is starting to get advanced in age. And a friend is saying like, why don't you slow down? And Diogenes is sort of taken aback by this. He says, why would I take it easy now that I'm old? He says, if you were running a distance race, would you slow down when you were approaching

• 20:28Ryan Holiday?

  the finish line? He says, wouldn't I do better to speed up? And this reminds me of one of my favorite stories about Marcus Aurelius. Marcus Aurelius is an old man. He's considered wise, he's considered powerful, he's a philosopher king. And he's seen leaving the palace in Rome. And a friend stops him and he says, you know, where are you going? And Marcus says, I'm off to see Sextus the philosopher to learn that which I do not yet know. The man's amazed. He says, here we have the king of the Romans still taking up his tablets and going to school. Epicurus, another philosopher from around this period, says sort of the same thing, that to say that you're too young or too old to learn is to say that you're too young or too old to be happy. Like, this is the whole point of existence. And so I think Diogenes is right here. We should not just become students at some early point in our life, but we have to stay

• 21:12Ryan Holiday?

  students at all points of our life. We always have to be learning. And while we are alive, we should be living. And so what makes Diogenes so great? What's motivating him? He's not trying to be rich. He's not trying to be famous. He's not trying to be important. He's not trying to be a great athlete. In fact, he thinks it's interesting that people compete in all these areas and not the area that actually matters. We're told that he says, I see many men competing in wrestling and running, but no one competing in the pursuit of human excellence. So that's what Diogenes is after, sort of human excellence. He's trying to get to the core of the human experience. What actually makes a great and powerful person?

• 21:57Ryan Holiday?

  And he believes it's not all these It's not status. It's not any of the things that other people are after. It's something deeper, something more profound. And that's what makes him this great philosopher. And lastly, I think one of my favorite lines from Diogenes. He's asked like why he changed his opinion about something. Right? We would think that a philosopher would be consistent. And he says, look, I used to piss my bed, but I don't do that anymore. Right? The point is, a philosopher should be able to change your mind. Cicero talked about this, about remaining a free agent. Things are always changing and we should be able to change. Marx realist talks about how if someone brings you new information, they point out where you've been mistaken. They're not harming you. They're helping you. They're helping you become what you need to be. But that can only happen if you change.

• 22:42Ryan Holiday?

  If you're willing to change your mind, if you're willing to change your practice, if you're willing to incorporate this new information in. And I think we should even think about this with Diogenes. A lot of what he says might make us uncomfortable. It might question some assumptions we've long held. But he knew what he was talking about. And in hearing from him, he can help correct us. He can help guide us. He can help point us in the right direction. Maybe you love the Stoics. Maybe you're a Christian. Maybe you prefer the Eastern thinkers. But there's something in Diogenes, something in the cynics, even if it's not totally practical, even if it's a little too extreme for some of us, that can help us question things. It can help us think about things from a new perspective by taking things to a logical extreme or by subjecting them to extreme circumstances.

• 23:27Ryan Holiday?

  Diogenes helps us understand ourselves, our own assumptions, our own ideas better. Seneca talked about this too, how we want to read like a spy in the enemy's camp. I think studying other schools of philosophies help us understand and improve our beliefs as a result.