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A
Welcome to the daily Stoic podcast, designed to help bring those four key Stoic virtues, courage, discipline, justice, and wisdom, into the real world. 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. 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, 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? Even 2000 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's wandering. He's showing you how to stop wandering yourself. 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, right? 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. 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? 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. We 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?
B
Right.
A
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. The first Greek historian, Herodotus, is remarkably late. You know, in this process and not super widespread, so. 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 kind of moral dilemmas and the flaws and foibles of humans throughout history.
B
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 know, you see this in the Bible, Right. I 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.
C
Yeah.
A
And the idea that, yeah, you hear the Odyssey as a kid and it means something to you, and then you, 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. And 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 reengage with and take different things from them as you get older.
B
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. You know what I mean? And it's like, wait, I thought you were in love with. 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. Yeah, just go, you know?
A
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, you know, knows the monster? Is it skill? Which one's the monster?
B
Skill is the monster. Charybdis is the toilet bowl whirlpool. Yeah, it sucks.
A
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. 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, and 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. Like, you won't have any moral responsibilities, but if you change it, you are, in fact, killing by your hand, one person. And so. So it wasn't until I reheard 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. This is leadership. It's having to make these incredibly painful decisions in which some people will lose something. And that is the awfulness of being in a position of responsibility.
B
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's. 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, you know, moral lessons in all of this. One of the, one 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 her. 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 going to 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 going to, we're going to go through and we're going to, we're going to roll the dice and we know we will probably lose men. And that's a really, really hard decision to make.
A
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. But 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, is teaching. And there is something about, there's, 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, 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.
B
Yes, exactly. As your Kennedy reference before points out very clearly. But 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. Of the show, 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, but 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. Okay? 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 was. 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, and that's what we're hoping kids take away from it.
A
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, right? 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's not someone you would want to be.
C
Right?
B
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'm. I can't. I'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. 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, and it's something that is not necessarily new, and I think we can take comfort in that. You know, when you hear these stories,
A
to me, you mentioned Gilgamesh earlier. What's so fascinating about Gilgamesh is Gilgamesh and the Odyssey. Let's say they're. They're two equal foundational epics. But Gilgamesh was only discovered in the 1800s.
B
Right, exactly.
A
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's, It's. It doesn't have the same resonance. So it's. It's not actually that the Odyssey is so great, it's that people believed it was great for 2000 years, and now it. 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.
B
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 had 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 mythopoeic impulse of these stories, and these kind of connectedness of how similar they are.
A
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C
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. Yeah, 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? Why does it have to. Why does it never seem to catch fully.
A
Yeah.
C
Why does it have to keep getting reinvented?
A
I was thinking about this with the title of your book, the idea of the Sirens. It's fascinating to me because my 8 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 gonna go home or how you were gonna go home. It wasn't just that they were these beautiful, seductive or talented singers. It's actually what they were saying that. That drew people to the rocks.
B
Yeah.
A
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, you know? Well, yeah, because, you know, we. We often think of misinformation as this thing that sort of plants ideas in people's head or propaganda as planting ideas in people's head. But actually, it's much more insidious in that it. It usually tells you something that you want, on some level, to be true. Yeah. 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. That your specific predilections, the things you want to be true, can be found pretty quickly with. 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. And. And. And that. 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 he's just like, of course he did. Right. You know, doesn't he kill the suitors?
B
But bow and arrow.
A
Well, he and his son Telemachus, they slaughter them. You know, it's a very brutal ending, which I had to skip over, but the point is. Oh, you mean to your son.
C
Yes.
A
Yes. The point is, some parts. Why would you Skip over that? 6 felt a little young to have a hundred people be murdered. 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.
C
Foreign.
A
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Podcast: The Daily Stoic
Episode: We Are All Kings Now | Why We Can’t Stop Talking About The Odyssey
Date: July 24, 2026
Host: Ryan Holiday (A), with guests (mainly B and C)
In this episode, Ryan Holiday explores how Stoic philosophy and ancient stories like The Odyssey continue to resonate in the modern world. The conversation delves into the personal and societal responsibility that comes with freedom, how the lessons from myths function as lasting parables, and the deeper, often missed, significance of classic works. The discussion also unpacks the enduring relevance of The Odyssey’s dilemmas and metaphors, relating them to leadership, morality, and personal growth in today's context.
The conversation is engaging, reflective, and scholarly—balancing reverence for ancient texts with a candid assessment of their messy, difficult lessons. The hosts use a conversational, relatable tone, frequently referencing personal experiences, storytelling, and modern parallels. The overall message: classic myths like The Odyssey are not lessons in hero-worship but ongoing, living guides to grappling with responsibility, temptation, and the hardest choices in life. Their true power lies not in trivia, but in their ability to adapt and teach, generation after generation, helping us all answer what life is actually asking of us.