The Daily Stoic - Rich Roll & Ryan Holiday on The Odyssey’s Biggest Moral Questions

Episode Date: August 13, 2026

In this episode, podcaster, author, and endurance athlete Rich Roll invites Ryan onto The Rich Roll Podcast to discuss the biggest moral questions at the heart of The Odyssey. Together, they wrestle with the same questions The Odyssey has posed for thousands of years: What makes a good leader? When is deception justified? And what happens when ego takes over?Listen to the rest of their conversation on The Rich Roll Podcast on Apple Podcasts, Spotify, or watch the video on YouTube. 📚 Pick up a copy of Rich Roll's book, Finding Ultra: Rejecting Middle Age, Becoming One of the World's Fittest Men, and Discovering Myself, at The Painted Porch: https://www.thepaintedporch.com/👉 The Rich Roll Podcast | Apple Podcasts, Spotify, YouTubeFollow Rich Roll | Instagram, X, Website🎟️ DAILY STOIC LIVE | Ryan Holiday is coming to a city near you! Grab tickets here |  https://www.dailystoiclive.com/🎙️ AD-FREE | Support the podcast and go deeper into Stoicism by subscribing to The Daily Stoic Premium - unlock ad-free listening, early access, and bonus content: https://dailystoic.supercast.com/✉️ FREE STOIC WISDOM | Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemailSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Welcome to the Daily Stoic Podcast, designed to help bring those four key Stoic virtues, courage, discipline, justice, and wisdom into the real world. Hey, it's Ryan. Welcome to another episode of the Daily Stoic Podcast. Look, what I love is when ancient ideas sort of break containment and come back into the modern world. I don't mean like retrograde, bad, antiquated, and antiquated. machronistic things. I mean when elements of what they would call the great conversation, that's what philosophy is, that's what ancient literature is sometimes referred to,

ceases to be this thing that they used to do. And it comes through not just to people like me or you that are listening to this podcast, but like mass culture. That's what I think is so awesome about Christopher Nolan's The Odyssey. Whether you like the movie or not, the fact that you have an opinion about the movie that the Odyssey is being talked about right now is fantastic. It's how it was supposed to be. We don't talk enough about these ancient myths and stories, which are supposed to be living, evolving things, right? Every generation rediscovers, reinterprets,

adds new takes and understanding of these ancient ideas, which is, by the way, what they were in the ancient world. You think about, by the time Marx realist comes along, the Odyssey is much older to him than Shakespeare is to us, to us, right? It's almost as ancient to him as he is to us. So these ideas were always old. They were always being discovered and reinterpreted and re-talked about. Virgil's the Aeneid is a response in many ways to the Odyssey, but set from the perspective of the Romans. So I love this. I saw the movie. I thought it was great. Last year when I was in Greece, we went to Ithaca and I shot

some stuff there. You might have seen that on social media. It was funny, you know, to record stuff a year ago and then just to sort of watch it blow up. But that was, that was cool. I guess it's a reminder that timing is everything. The content you could say had its own little Odyssey, mostly sitting on a hard drive. But the point is, I've been talking about the Odyssey a lot. So I was really excited when my friend Rich Roll sent me a text. He and I were going back and forth about the movie. He's like, let's hop on a podcast and let's just talk about it. And we did, which, by the way, I would have done Rich, if you're listening, even if we weren't recording. Because, That's what I'm saying. That's what I love to talk about and I love to kick around. That's what great art does, right? It brings people together. Even when they have divergent views, it's bringing them together to talk about that thing. So this is a chunk of that conversation that Rich and I had. If you don't listen to the Rich Roll podcast, you should. I've been on a bunch of times. It's one of my favorite podcasts. Rich is a super thoughtful guy. He doesn't usually do these remote. I does it in his amazing studio there in Southern California, which I've been out to many times. You can check out those episodes or is really

high-produced podcast with awesome people, some of the best athletes in the world, some of the best artists in the world. He even had Bruce Dickinson, lead singer of Iron Maiden on, was it last year, 18 months ago. Anyways, one of my favorite podcasts,

we carry his book, Finding Ultra in the bookstore. He's been on the podcast. His dad, David Roll has been on the podcast. He wrote a great book about Marshall, a great book about Truman. If you want some more Odyssey Conversations, stay tuned,

listen to this, and then follow, at Rich Roll Everywhere, listen to Rich Roll Podcasts, and we'll get into it. Back to School starts now. Get long-lasting battery life on the Dell XPS laptop powered by Series 3 Intel Core so you can work from anywhere. And now starting at $699 with exclusive student pricing starting at $5.99. It's lightweight, portable, and packed with enough processing power to make multitasking a breeze. So say goodbye to distractions and hello to more free time.

because you finished your work faster. Complete your setup with savings on select monitors and more must have electronics and accessories. Limited time deals and free shipping on PCs and more await you at Dell.com slash deals. That's Dell.com slash deals. There's a ton of information out there about what you should do to be healthier. People trying to sell you this, people trying to sell you that, people trying to tell you to do this, people trying to tell you to do that. Everyone's got an opinion and it's hard to know which one to listen.

to. And that's where today's sponsor comes in with superpower. You do one simple blood draw that gives you information on over a hundred of your blood biomarkers. By the way, your annual physical only does like 10 to 15. And this testing gives you a much deeper understanding of your body across 17 core systems, heart, metabolism, thyroid, inflammation, and even environmental toxin. And then once you have this information on your body, you can do so much more with your health. And superpower makes the process easy. They send a licensed professional to your home or you just visit a nearby lab. And then superpower gives you actionable suggestions for your unique results. Supplement recommendations, prescription suggestions, things to take to your doctor,

things to take to your doctor, all of that. It's not just a one-time snapshot. It tracks your results over your lifetime. As I said, superpower is the most affordable 100 plus biomarker blood test starting at $199 and it's HSA-FSA eligible. Take control of your health with superpower and for a limited time, our listeners will get $20 off to unlock their new health intelligence. Head over to superpower.com and use code stoic for $20 off your $199 superpower membership. Tell them the Daily Stoic sent you to support the show. I'm super excited to talk to you, Ryan. You are well-known worldwide for being an expert on Stoicism and Greek philosophy generally, we're having a monoculture moment that you must be relishing

where everybody is celebrating this old poem by dint of Christopher Nolan's, I'll say it right now, masterpiece, I love the movie, saw it a second time last night, and you have been posting lots of videos and this YouTube video with your thoughts on what we should understand from the Odyssey, what's important to understand. And so I thought it was an opportune moment to just get you on here and have you share your reflections on Homer's Odyssey, Nolan's Odyssey,

and how you're kind of synthesizing this and interpreting it for us. So first of all, I guess, like, how did you like the movie? Well, I should stipulate here that I know it not as a classicist. I don't speak Greek or Latin. I know it as a regular. person who has been fascinated with it, who studied it with its connection to sort of stoic and other sort of forms of philosophy. And then my nine-year-old son got very excited about it. And so I've sort of

hit it from a bunch of different angles, but all of these angles much closer to a layperson than, say, like a translator's, right? So I do feel like I was able to enjoy the movie on a couple of different levels and I really did enjoy the movie. I thought it was spectacular. I have some quibbles here, there. But I think what we have to understand is the Odyssey, like all of the other Greek myths, was both a form of art. It's beautiful language. It's evocative. It's entertaining. It's all this. But then it was there in a way that we don't always understand art and entertainment to be today, which was a means of communicating ancient wisdom and timeless moral truths. So, you know, like if you watch a Greek play, you know, like Shakespeare, all the actors are

men, but they're not really, like they wear these masks. The acting is not the key in a Greek play or in a Greek tragedy. It's the language. It's the, it's the lessons. It's the lines. And so I think the problem is we don't always understand art as being that. Like, you know, most fiction today is almost like, I want to say it's almost amoral and that it's like designed not to teach moral truths, but to question moral truths. And so if we understand the Odyssey as being this sort of story that was told and retold and retold for thousands of years, each generation sort of thinking about the same truths, but bringing their own interpretation and understanding that. of them, their understanding of Odysseus, for instance, the understanding of Odysseus is

dilemmas throughout the play, then you should actually appreciate both what Nolan did in telling it his own way, and you should appreciate the arguments over it, right? Like, that is the point, is that each generation reads the Odyssey differently than the generation before, and then each new medium that we're able to tell it, and including going from an oral tradition to a written tradition is going to fundamentally change. The medium is the message. So each generation in telling and retelling it and how it captures it, whether it's with film or radio or a television miniseries versus a blockbuster, all of this is changing the story and allowing us to see it in a different way, which is the whole point. Yeah, the assignment is the interpretation. There is no

one singular odyssey. There is this, you know, original text. I suppose we're not even sure that Homer was one person. Every interpretation or translation is different, and it kind of evokes the lens of the translator. And right now, we have Emily Wilson. Her translation is apparently a primary influence on Nolan's version, his interpretation in this movie. It's been interesting to see the discourse around her kind of like review of the movie, like her celebrating the fact that this is a monoculture moment and it's kind of exciting in that regard, while also her taking issue with how he has interpreted it. But I think that that is, you know, part of what is exciting about this. It is the clashing of these interpretations and how different

people see it differently. Like, who is this character, Odysseus? And what, you know, what is it about him and this story that is so indelible that has made it the architecture for all stories and a tale that has withstood, you know, eons of time and is still relevant today. That's the debate that we should celebrate, and that's what the conversation is about. And I think that's very different than, you know, hey, should Helen be black or not? Is it okay to have a trans person in her not? Like, which is one of the points that I want to make. And I think Emily Wilson would appreciate given that she,

She wrote a famous biography of Seneca earlier in her academic career. But Seneca 2,000 years ago in one of his letters is lamenting just people totally missing the point of the Odyssey. And I think it's fascinating to think that 2,000 years ago people were having these debates about where was Troy and, you know, where were the different islands? And like did it actually happen or not? just like today we're like, is Homer really one person? Was he blind or not? And he was saying that this is not what it's about. Like, we're not supposed to be debating the trivia of the art, but we should be going to the essential questions of the art. And that ultimately we should understand that Odysseus in his Odyssey is a reflection of the human undergoing any kind of ordeal,

battling their sort of higher self and lower self, you know, the people. perils of hubris, the impossibility of ever returning home, you know, that he's saying, like, if you don't see the, if, if what you're debating about the Odyssey is not the philosophical questions, then you're just, you know, you're, you're just engaging in culture war nonsense. Obviously, he wouldn't have used that term. And I think it's sad that it's devolved into sort of culture war nonsense. But if, if that's what you're fighting about, then you're part of the problem, right? Like, I think there's like, lot of things to argue about in the Odyssey. And there's a bunch of issues I take with, I would argue over

interpretations and arguments that Nolan's Dysseus and Odyssey are making and how they, not like because, oh, you have to be true to the text, but this choice versus that choice, you know, fundamentally changes the arc of the story. I'll give you a really good example. So like the whole, and are we cool with spoilers? Yeah, I think so. Yeah. Okay. The, but they, The cat should be out of the bag by now, 3,000 years later. But I think the premise in Nolan's Odyssey is that this sort of law of hospitality, how we treat strangers, how we treat others, and we violate this at our peril. And so the tale of polyphemous, the interaction with the Cyclops, is so fascinating because in my, again, my children love this story, you know, Odysseus in the poem, you know, he introduces himself. as that his name is no man.

He tells Polyphemus that his name is no man. So then when they blind polyphemus and he's screaming to the other cyclopses, which also don't exist in the movie, they say, who hurt you? And he says, no one has hurt me or no man has hurt me. And they say, okay, well, if no one has hurt you, shut up, this isn't a problem. And then he goes away. And then Odysseus, having escaped, shouts out at him, hey, actually, it wasn't no one that hurt you. It was me, Odysseus, Sacker of Cities that did it, and you'll know my fame.

And so it's this moment of hubris and ego where Odysseus needs credit for what he inflicted on polyphemus that sets in motion the central conflict of the book, which is he's cursed by the gods. So that's missing. And I think people will recognize that. But to me, the critical choice that Nolan makes is that they walk into the cave, they start to sense something is amiss. and then the cyclops walks in and then begins eating them, right? So the cyclops is indisputably the monstrous villain of the encounter. But in the poem and in the most retellings, Odysseus and the men walk into the cave, see that it's full of sheep, slaughter the sheep, and eat them,

and then polyphemus comes in and is enraged that someone has killed his sheep. And so it's actually Odysseus first who violates the law or oversteps. And polyphemus is, although monstrous and eats humans, is somewhat righteous in his anger. And then Odysseus is cunning in his craftiness for getting out and then egotistical in claiming credit and then bringing the wrath of gods upon him. So it's like obviously you have to simplify it in the movie, but I do think this is an essential simplification because first off, it makes it simple. And the whole point is that the Odyssey is complicated and it's hard to know who the good guy is.

But also the idea that Odysseus just shoots Polyphemus with an arrow when he escapes, and this is what makes the gods angry is really not what is the driving force of the Odyssey going forward. It strikes me as a. glaring omission if you're trying to underscore the hubris of Odysseus. But the way that I make sense of that begins with the Chiron at the very beginning of the movie where it says this is a time of apparent magic. And I think the word apparent is important. I think what is telegraphing is that this is a story of unreliable narrators. And the way that Nolan plays with time and narrative is through the whole movie is anchored in a recounting of what happened through the perspective of a

couple different people. It's Odysseus telling the story to Calypso when he's on the island with her, and it's Menelaus sharing what he remembers from the Trojan War to Telemachus. And so we have to question whether these recollections or the way that these stories are being told are actually what happened or a version of what happened that suits the internal narrative of the narrator. And I think when you think of the way that Odysseus is recollecting what happened and, you know, his version of what went down with the Cyclops, maybe he conveniently decided to omit that part because confronts him with his own guilt. And his guilt and his trauma and this PTSD that he's suffering seems to be what Nolan is most interested in. And he's interested in it because this is his portal into wedding

this ancient story with what he, with his perspective on what's happening right now in modern society. And for me, that's what makes this version, his interpretation, so resonant, because it seems so current with what we're seeing around us at the moment. And this is something that you talk about a lot through the lens of Stoic philosophy. this degradation of kind of our moral center at the moment, where if you look at what's happening in the House of Ithaca, you know, there's sycophants and people behaving badly, acting on their own self-interest in a very craven way.

And is this not simply a metaphor for the White House at the moment? It's like a hostile takeover. Yeah, it seems to be like where Nolan's interest is and why, you know, he felt urgently, about telling this story now. Yeah, it's about a collapse of the old ways. And I think he does a really good job, maybe a better job than I would have anticipated

or even considered of showing the collapse of the old ways all the way around back to even, you know, interpreting the Trojan horse as some sort of, you know, violation of the laws of war and trickery. Although it even goes back, you know, even further, there's a sort of, predecessor story to the Odyssey of why they get sucked in to this law of war. There's this,

you know, sort of party of the gods and they all make this pact about who's the most beautiful one. And it's a long story. But basically like, Odysseus doesn't want to go fight in the Trojan War. That's not something you see in this movie or in the Odyssey exactly. But Odysseus doesn't want to fight in the Trojan War. He tries to get out of it. And he actually claims that he's crazy at first. And he claims that he's crazy. And only by the test that they prove that he's not crazy, he's like plowing his field. And they lay telemachus down in front of him plowing his field. And when he stops to not run over his own son, that's how they realize that he's not actually crazy. And so the whole idea of this being this sort of insane war that shouldn't have happened in the

first place that he's sort of sucked into and fights in reluctantly because of this kind of pact that he'd made many years before. All these sort, like, I think what's so lovely about Greek mythology and about philosophy is that kind of the more you know about it, the more it operates on all these other levels. Like this would be a modern analogy, but it's like, you can't watch a Rested Development one time. You've got to watch it like 30 times. And then you understand that it's, It's operating on all these different levels and there are these callbacks. And so not only is the Odyssey something you should read and watch and read and watch again, but you should read multiple translations and then you have to read the other myths and then

you have to read the poetry about it and the stories about it and the interpretations of it. What you start to get each time is just a slightly different understanding of it. And from that, you're able to consider these questions from all these different angles. Each author has a different take on Odysseus, has a different take on Helen, has a different take on polyphemus, as we were talking about, is a different take on telemachus?

Has it, you know, is Odysseus a hero or is he a villain? Is he both? You know, is Agamemnon a hero or a villain? Is Helen a hero or a villain? You know, was she kidnapped or did she fall in love? or there's another version of it where she's like transported to Egypt. There's all these different versions of it. And so if we understand it more as like source material that people are riffing on over and over and over again, almost like a song sample, I think we understand a little bit more of what they're trying to do.

And then the idea is each one of these reads helps correspond to something ultimately in your own life. This isn't just like debating what style of painting is best, but this is like, okay, but what kind of person should I be? And what you find is that ultimately all these things come down to some of the most fundamental questions in philosophy and in life. Like the trolley problem is really interesting in philosophy, right? This idea of if you do nothing, the trolley runs over, was it five people? But if you pull this lever, it runs over one person, right? That's the trolley problem. But this is actually the choice. that Odysseus has to make between Silla and Carybdis. Although I always thought it was Charbitis because I never heard it out loud. Yeah, no, I'm pretty sure it's Carybdis. It is. But like he and he doesn't fully weigh it that much in the movie, but like between a rock and a hard place or sometimes you'll hear people say Silla and and Carybdis as just

meaning like a dilemma, like just a hard choice. But it's so much more than that. It's Odysseus has to choose between letting six of his men be destroyed for sure, or do they all go down in the whirlpool? And it's actually really interesting because in the movie, Nolan kind of has him trick the men into choosing for him. Like he kind of abdicates the moral choice. But as the band Rush would say,

even if you choose not to decide, you still have made a choice. This is still, he's still the moral choice. So anyways, I just think it's so fascinating that you have this poem from 3,000 years ago, accidentally chancing upon, or not accidentally, but chancing on this moral question that philosophers are still debating to this day.