

24 Jul 2026 · 22m · 7 chapters

The episode argues that the Odyssey isn’t about trivia (where Odysseus wandered, Penelope’s fidelity, timelines) but about moral self-mastery: “you are the king now.” It links Stoic philosophy and the U.S. republic to personal responsibility, checked by private virtue, and reads Odyssey monsters as inner forces (temptations, distractions, setbacks) that must be confronted to reach one’s “Ithaca.”
Seneca is cited as the Roman Stoic critic; Marcus Aurelius and Benjamin Franklin are referenced. Two modern guests discuss teaching/translation and storytelling for children (including Emily Wilson’s Odyssey translation) and leadership dilemmas.
Freedom requires citizens’ self-command; reading myths should change you; sirens symbolize personalized misinformation/temptation; Odysseus is a flawed, tragic figure.
Odysseus vs. Scylla/Charybdis as a “trolley problem” leadership choice; “nobody” as a hubris/cleverness moment; Sirens’ tailored promises; Odysseus’s brutal ending and the “no progress”/timeless repetition theme.
Written by AI. May contain mistakes.
Exploration of the responsibilities and temptations faced by leaders like Marcus Aurelius.
“For most of human history, somebody else, a king, a lord, a tyrant, a chief, was in charge.”
Discussion on the deeper meanings of The Odyssey and its relevance to personal growth.
“Even 2 ,000 years ago, people were missing the point of the Odyssey.”
The role of myths and stories in teaching moral lessons and philosophical principles.
“We have a few sort of syllabuses from different like Greek and Roman schools.”
Understanding the complexities and moral dilemmas faced by leaders in difficult situations.
“And the idea that, yeah, you hear the Odyssey as a kid and it means something to you and then you watch it when you get older, you read about it, that it's this text that stays with you your whole life.”
Exploring the tragic elements in Greek myths and their implications for modern storytelling.
“And, you know, he told his crew, just keep rowing.”
Learn about the tragic flaws of Odysseus and the deeper lessons from his journey.
“And they can look at it from a little bit more with a little bit more perspective and distance.”
Explore the enduring themes in The Odyssey and the seductive nature of the Sirens.
“What makes the great literature is that every generation or every different person sees something, sees it differently.”

Get the gist, explore an idea or ask about something said.
On The Daily Stoic, what are the key points of this episode?
Automatic transcript. May contain errors.
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: We are all kings now. For most of human history, somebody else, a king, a lord, a tyrant, a chief, was in charge. In ancient Rome, that was the emperor. Marcus Aurelius was the most powerful man in the world. He could do anything he wanted. No one could tell him what to do or not to do. This was not all fun and games, of course, since this not only presented him with incredible amounts of temptation, but also an enormous amount of responsibility and stress. He had to make a lot of decisions for both himself and for other people. As we've said many times, in light of the checks and balances, Marcus Aurelius had to turn to philosophy.
0:56Ryan Holiday: He had to fight to be the person philosophy tried to make him, as he said in meditations. That's a lot to ask of a person. That's a lot to put on a person. And this is ultimately what makes the decision that the founders made 250 years ago in America so radical. They were essentially putting that on every person. What the founders were attempting was an extraordinary historical break, a nation where people were free to be in charge of themselves and where the people were responsible for their own government. It's a republic, Benjamin Franklin famously said on the final day of the Constitutional Convention in September 1787.
1:40Ryan Holiday: If you can keep it. The founders themselves were under no illusion about what they were asking. Such an experiment could only work if checked by private virtue. Without citizens willing to do the private work of getting command of themselves, their impulses, their emotions, their passions, their fears, their appetites, without this, freedom would collapse into chaos. You are the king now. The republic is in your hands. Can you keep it?
2:22Ryan Holiday: Even 2 ,000 years ago, people were missing the point of the Odyssey. That's an argument that Seneca makes. He's saying even the smartest scholars and the biggest fans of his time were missing the point. He said that people would get in these debates about where Odysseus got lost, about whether Penelope was faithful the whole time, whether Homer was the first of the great poet, whether Achilles was older than Patroclus. Seneca said, none of this matters, not even a little bit. He said, I don't care where Odysseus wandered. He says, Homer isn't telling you about Odysseus' wandering. He's showing you how to stop wandering yourself.
3:09Ryan Holiday: He says the argument isn't about whether Penelope was pure. He says, teach me what purity actually means and how to live it. Seneca is pushing back on all those pedantic, obnoxious English teachers, those classicists, for whom the geography, the timeline, the trivia is what matters. But that isn't what matters, The story of the Odyssey is what it's doing to you right now while you're reading it. Odysseus isn't some guy who gets lost in the Mediterranean. He's you right now getting knocked off course by something you didn't see coming. The monsters in the Odyssey are not literal monsters. They are parts of yourself.
3:53Ryan Holiday: They are things out in the world that you are fighting. The sirens are the temptations you are facing in your life. the distractions, the things that are pulling you off the path that matters, that you're supposed to be on. The storms are setbacks. Ithaca is whatever you are trying to become, whatever destination you are trying to reach. Seneca is saying that memorizing the poem and breaking it down into little pieces isn't the point. The point is, what does it teach you? How does it change you? How does it make you braver? How does it make you craftier? How does it make you more cunning? How does it get you to face what you have been avoiding?
4:36Ryan Holiday: How does it make you more loyal? How does it make you more determined? How does it make you a better host and a better guest? How is it pushing you to complete your own odyssey? That's the question Seneca says we should be asking about the Odyssey. Not what happened to Odysseus, but what is this story asking of me and am I answering? What is life asking of me and am I answering? He thinks that this is the story that's supposed to help us slay our own monsters, sail through our own storms, get back to our own Ithaca. That's what the Odyssey is all about. That's what people keep missing. We have a few sort of syllabuses from different like Greek and Roman schools.
5:25We understand how the tutors taught the children. And one of the ways they did it was that everyone would be familiar with the Odyssey. Everyone would be familiar with the founding of Rome, all these different stories. And then the students were encouraged to debate and question these literary events as if they happened. Like, why did Odysseus do X, Y, or Z? Should he have done X, Y, or Z? And so the idea that these myths were really these sort of jumping off points for these intellectual discussions, because we have to remember they didn't have history the same way that we did. You know, the first Greek historian, Herodotus, is remarkably late, you know, in this process and not super widespread.
6:09So, so they just didn't have like, Hey, here's all the things that have happened. And we know they happened because we fact-checked all of them. The myths were a way to just discuss these kinds of moral dilemmas and the flaws and foibles of humans throughout history. Right. Yeah. I mean, it's so enjoyable to sort of sink your teeth into those myths in that way, When we all can, I mean, I think honestly, all storytelling is that, right? I mean, in some ways we're trying to kind of understand the world around us, but you're absolutely right in that the idea is they're parables in a way. And you see this in the Bible, right?
6:49I mean, that was the way, you know, in the Christian religion, that was the way Jesus taught people through parables. He told stories and the old Testament, you know, some religious scholars believe a lot of those were just parables. They're not saying, hey, yes, Methuselah lived to 900. We're trying to take the point of the message of the story. It's not necessarily what happened blow by blow, but what is the message? What is the meaning behind it? And I think that's, you know, we're all sort of trying to find the meaning behind our own human experience. So stories, I think, help us learn that and celebrate that and express that all at the same time.
7:25Yeah. And the idea that, yeah, you hear the Odyssey as a kid and it means something to you and then you watch it when you get older, you read about it, that it's this text that stays with you your whole life. And your understanding of the different dilemmas and the different choices should evolve as you get older. You know, at first you hear, you know, Odysseus saying, you know, my name is nobody and it's just kind of a funny play on words. And that's what strikes you. And then you realize, oh, you know, had he had he kept up the fiction, he would have gotten away with the whole thing. It's this moment of hubris.
7:59And so as you get older, your understanding of the story, you notice different things from it. And so these were not just these texts that you're supposed to hear once, but you're supposed to engage with and re-engage with and take different things from them as you get older. I can remember as a student, you know, when we read The Odyssey, and I was, I think, in middle school or early high school, and there was the story about him, you know, going to the island with Cersei. And he wanted to go home, right? He stays with Cersei. And yet he falls in love with her. He stays with her. They have kids.
8:33You know what I mean? And it's like, wait, I thought you were in love with what you were just like, why? Just go home. Just go home. But as you get older, you see the complication of human emotions. You understand that within context. As a kid, you're like, dude, just go home. Just go, you know? Well, actually, it wasn't until I heard your episode about Scylla and Charbitis. This is where the saying between a rock and a hard place comes from. But Odysseus knows he has to navigate through this thing. And he knows that, what is it, Charbitis? that he knows the monster or is it skillet which one's the monster skill is the monster charybdis is the toilet bowl whirlpool yeah yes it sucks so he knows he knows the monster which has four heads is going to claim four of his men and he knows that every other ship sinks because they try to avoid the monster uh and and so he has this dilemma of leadership which is effectively the trolley problem i don't know if you know the trolley problem which is one of the main problems in moral philosophy, which is, you know, there's a streetcar careening down some tracks, and it's about to run over four people.
9:40And you can pull a lever and change it, and it will only kill one person. What should you do? Right? And it's this vexing dilemma, because if you do nothing, four people will die, but it won't be your problem. You won't have any moral responsibilities. But But if you change it, you are in fact killing by your hand one person. And so it wasn't until I re-heard the story as you were telling it in the podcast that I go, oh, wait, Odysseus has to make this choice where he has to lead four men unwittingly to their deaths or by deception lead them to their death or the whole crew will die. And this is leadership is having to make these incredibly painful decisions in which some people will lose something.
10:29And that is the awfulness of being in a position of responsibility. Exactly. And, you know, he told his crew, just keep rowing. Just no matter what happens, keep rowing. He knew what was going to happen. He just didn't have a choice. And it was an awful, you know, Sophie's Choice type of moment for Odysseus. And I think all of us – I mean hopefully not very many of us, but all of us have to make awkward or hard choices in life, these no-win scenarios, unless you're Captain Kirk and you got out of the Kobayashi Maru. But I'm not going there. We're not going into Star Trek. I won't. But still, there are moral lessons in all of this.
11:09One of the – that particular point actually was brought up to us when we were writing the script. we have you know consultants professors that look over classics professors that look over our scripts and the late Diane Klein who was a fantastic professor and she just totally got the tone we were going for and she kind of knew when to say this is fine you're not really representing this correctly but she also had some really great suggestions and ads and she I remember her pointing that out she's like this is a really hard thing for Odysseus he has to pick career he doesn't have a choice because he knows if they go to the whirlpool they all die so he and he has no choice so rather than telling his men hey we're gonna face this monster or rather than stopping to try to fight the monster which a lot of people did he's like nope we're just gonna we're gonna go through and we're gonna we you're gonna roll the dice and we know we will probably lose men and that's a really really hard decision to make there's something i do like about the greek myths in that they don't baby anyone so you know obviously i love all the stuff that's for kids and we've done all that with our kids.
12:15But there is something about this, you know, magical pizza party book or whatever they're reading that is fun, but there isn't any, there isn't much weight to it ultimately in terms of the lesson that it is teaching. And there is something about, I think there's a reason they develop these stories and there's a reason these stories have survived for thousands of years is that they're there to teach the things that we do need to learn. If you're trying to groom someone for leadership, this is the kind of thing they need to be thinking about from the beginning. Yes, exactly. As your Kennedy reference before points out very clearly.
12:54But, yeah, it's always a joy for me because I think when we tell these stories, we're very mindful of the graphic nature of some of the content. We have to put a disclaimer on the top of the show. So, you know, and if it wasn't for cutting heads off and rape, the Greeks probably would have had nothing to talk about. It's always just part of everything that they do, especially with Zeus. But I also think that there's kind of an underlying sadness to most of these stories. You know, there are moments of joy, but there aren't a whole lot of happy endings. And we try as storytellers to find those moments of joy.
13:32But we also, as we tell the stories, try to keep the listener in remembering that this is a story. And I think that's where the Oracle of Wi-Fi really helps because we can break up the narrative, occasionally step back from the fourth wall. And when the kids are wrapped up in a story, they're like, oh, yeah, that's right. This is just a story. OK, so if they get too involved in the intensity, we can pull it back. And it gives them the opportunity to experience the story, you know, sort of as you're engrossed in it, as it's happening, but also as a, oh, yeah, I'm just listening to a story. And they can look at it from a little bit more with a little bit more perspective and distance.
14:09And that's what we're hoping kids take away from. Well, a lot of these stories are tragedies, right? And that's a genre that certainly we don't make for children much anymore. But it's also just a genre that is probably less popular. The idea of these sort of tragic figures with these tragic flaws, the purpose of like Odysseus isn't necessarily a hero. He's this flawed, you know, he's this guy there to teach us a bunch of lessons. And the other one I thought was so striking, it wasn't until I read Emily Wilson's new translation of the Odyssey that I and I read it a few years ago. I made it all the way to the end.
14:46Right. Which you sort of don't do as a kid. And it wasn't he gets home. And then what was so striking to me is that he gets ready to leave again. Like, yeah, right. It's not like he says, I'm going to spend the rest of my I'm never leaving from this this oasis ever again. And you go, oh, Odysseus is a tragic figure. It begins with him fighting in a war that he didn't believe in, spending 20 years to get home. And then he's wandering again. He is he's not someone you would want to be. Right. And it started the sad things. He didn't even want to go to the war. And he was trying to just he's trying to trick him and said, oh, no, I can't.
15:26I'm not fit for leadership. But it is a fascinating arc for that particular character, how he went from point A to point B and how different they are. And at the end, there is sort of an unsettled feeling for him that I would imagine, you know, a lot of people feel if you're, you know, if you were deployed, if you're in the military and you were deployed and you come home and suddenly you have to figure out what to make for dinner. and you spent the last 18 months trying to figure out how you're going to keep these people alive, that's a big mental switch. You know what I mean? And I think it has a profound effect on human beings.
16:02And it's something that is not necessarily new. And I think we can take comfort in that, you know, when you hear these stories. To me, you mentioned Gilgamesh earlier. What's so fascinating about Gilgamesh is Gilgamesh and the Odyssey, let's say they're two equal foundational epics. But Gilgamesh was only discovered in the 1800s. And so what we don't have is 2 ,000 years of paintings and poems and adaptations and plays and then movies. We don't have all of the art built on top of the art. So it doesn't have the same resonance. So it's not actually that the Odyssey is so great. It's that people believed it was great for 2000 years.
16:48And now it's there's just a it's like there's a nostalgia or a hominess to it that just feels familiar because you've known about the Odyssey from before you knew about the Odyssey. Right, exactly. It's part of the fabric of who we are. And, you know, the Mesopotamians wrote on stone tablets. Thankfully, they did because they lasted a lot longer. But yeah, I mean, if they'd used papyrus, we might never know about Gilgamesh, but it is, it's always intriguing to me too, to find the similarities in these themes, that mythopoic impulse of, of these stories and these kinds of connectedness of how similar they are.
17:24It's amazing to me.
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19:23Ryan Holiday: That's ironwall.com slash Daily Stoic. Stop online threats before they become real world attacks. And there's a link in the show notes. What makes the great literature is that every generation or every different person sees something, sees it differently. Right. And so, like you say, you take something like the Odyssey, which my nine year old is obsessed with. So we've been, you know, just listening to it and listening to songs and finding poems. And then we had to go to Greece. But what's so fascinating to me about the Odyssey is that, you know, when I was younger and when I first read it, you know, Odysseus is the hero.
19:58Ryan Holiday: and then you read something like Tennyson's poem about Odysseus and you go, oh no, Odysseus is a cursed, tragic figure who wants desperately to come home but can't actually be home. And that you wouldn't want to be Odysseus just like you wouldn't want to be Elon Musk. It's actually miserable and awful.
20:24Stephen Greenblatt: I mean, Dante thought the same thing about Odysseus, as you know, even though Dante hadn't read Homer, but he understood already from the story that there's something wrong with something tormented about this figure. I mean, you might not want to be Odysseus, but you also, the question is, Odysseus is the only survivor of all the people who leave. So everyone in his ambit dies in the course of his attempt to get back to Ithaca. One thing to say, I suppose about all of this is that, and that again, obsesses people like us, is that there's no progress in all of this, which is very strange. I mean, you'd think, because we're talking about things that were written a very long time ago, and if we think that they're really intelligent, as we do, and deeply perceptive, as we do, the question is, why does it have to keep getting repeated over and over again?
21:21Stephen Greenblatt: Why does it have to, why does it never seem to catch fully? Yeah. Why does it have to keep getting reinvented?
21:28Ryan Holiday: I was thinking about this with the title of your book, The Idea of the Sirens. It's fascinating to me because my eight-year-old is obsessed with the Odyssey, just how timeless that metaphor is, right? And that what I was fascinated to learn about the sirens. I don't know. I guess I just, I knew they said seductive things, but like when you actually read the Odyssey, they would often just tell people what they wanted to hear. They told stories about when you were going to go home or how you were going to go home. It wasn't just that they were these beautiful, seductive or talented singers. It's actually what they were saying that drew people to the rocks.
22:11Yeah.
22:12Chris Hayes: And that you that it's different for everyone. What pulls you in? Yes. And what compels you to your speeds you to your death?
22:22Ryan Holiday: You know? Well, yeah, because, you know, we often think of misinformation as this thing that sort of plants ideas in people's head or propagandas planting ideas in people's head. But actually, it's much more insidious in that it usually tells you something that you want on some level to be true. Yeah.
22:39Chris Hayes: And it's that part of what's so crazy about the landscape that we occupy now is how individuated it all is. Right. That your specific predilections, the things you want to be true, can be found pretty quickly with the algorithm and, you know, through this sort of sorting mechanism to lull you, to get you to, you know, to compel your attention. Yes.
23:01Ryan Holiday: And that it really can create in the way that the sirens could individualize the message to be as seductive as possible. That is technologically feasible in a way that never was before in a sort of previous mass media environment. so many parts of the odyssey are inexplicable you know as he gets there not to spoil the ending but there's just this sort of moment at the end where he just you know murders with his bare hands like a hundred people and it's like of course he did right you know doesn't he kill the shooters bow and arrow well he and his son tell him because they slaughter them you know it's a very brutal ending which i had to skip over but the point is i mean to your son yes yes the point is some parts are just skip over that six felt a little young to have a hundred people be murdered?
23:50Ryan Holiday: Not for me, I tell you, not for me. This may have been why you ended up writing the 48 Laws of Power. Someone told you some dark stories when you were six. Very true.
You’re the king now. The Republic is in your hands. Can you keep it?
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Featured guests in order of appearance:
Kenny Curtis | Full episode on Apple Podcasts, Spotify, YouTube
Stephen Greenblatt | Full episode on Apple Podcasts, Spotify
Chris Hayes | Full episode on Apple Podcasts, Spotify, YouTube
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