The Daily Stoic - BONUS | 12 Stoic Lessons from The Odyssey

Episode Date: September 23, 2025

For nearly 3,000 years, one story has ruled them all. The Odyssey. In today’s episode, Ryan shares12 Stoic lessons hidden inside this timeless epic.👉 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/🎥 Watch today's episode on The Daily Stoic YouTube channel: https://www.youtube.com/watch?v=kFi870MqlKM📖 Preorder the final book in Ryan Holiday's The Stoic Virtues Series: "Wisdom Takes Work": https://store.dailystoic.com/pages/wisdom-takes-work🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.com/dailystoicpodcast🎥 Watch top moments from The Daily Stoic Podcast on YouTube: https://www.youtube.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 FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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We're calling it Daily Stoic Premium. And with Premium, you can listen to every episode of the Daily Stoic podcast, completely ad-free. No interruptions, just the ideas, just the messages, just the conversations you came here for. And you can also get early access to episodes before they're available to the public. And we're going to have a bunch of exclusive

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history's greatest men and women to help you learn from them, to follow in their example, And to start your day off, with a little dose of courage and discipline and justice and wisdom. For more, visitdailystoic.com. ever told. It is a story that has been told and we told, adapted, and changed. It's inspired poems. It's inspired paintings. It's inspired music. Liam Neeson just made a movie about it. Matt Damon and Christopher Nolan are making a movie about it right now. I'm talking, of course, about The Odyssey. And it's a favorite of many people, but most of all, the Stoics. There is no work that the Stoics reference more than The Odyssey. I'm Ryan Holiday, the author of The Daily Stoic,

and I traveled thousands of miles, not just to ancient Greece, where, of course, the Odyssey is set, but to Ithaca itself, where it begins and ends. To find out not just what the Odyssey is about, what it can teach us about life, but also why it's so resonated with the Stoics and why it's resonating again today. Odysseus would not have survived his Odyssey without the help of Athena, But his son Telemachus would not have survived without Athena either. And I think it's illustrative the form that Athena takes, particularly when she is aiding Telemachus. She pretends she is an old family friend named Mentor.

Basically, Odysseus and Telemachus are a product of their mentors, as we all are. Perhaps this is where the word comes from. But the idea is that we are guided by the people who teach us, who have been further ahead than us. Mark Surrealis is mentored by Antoninus. Zeno is mentored by Cretes. I was mentored by the great Robert Green. The idea that you want to learn these lessons by painful trial and error is insane. You want to benefit from the experience of others. That's the joke. Any fool can learn by experience. I want to learn from the experience of others. And Odysseus does this. He is aided constantly throughout the Odyssey by Athena and then Telemachus as he is

coming of age. This is when he is approached by mentor as she is organizing the homecoming. You have to figure out who your mentors are in life. We are a product of our mentors. This is a valuable lesson inside the audits. I think it's one of the great warnings against ego from ancient literature. That's Odysseus behind me, right? So Odysseus has defeated polyphemus. He stabbed him in the eye. He's escaped the cave and he's gotten away with it, right? He's not just gotten away with it, but Polyphemus, the Cyclops, has no idea who Odysseus is. Because when Polyphemus had asked Odysseus his name, he'd said, my name is no man, or my name is nobody. So when the other cyclops had said,

who'd hurt you, who'd done this? Polyphemus said, nobody did this. Nobody has hurt me. So Odysseus has gotten away with it. And as he gets safely to his ship and he's sailing away, what does he do, though? In an act of hubris, needing to get credit for his brilliance, he shouts out, want to know who did this to you? Odysseus Sacker of cities did this to you. And it is in this moment that he seals his fate, that he prevents himself from getting back to Ithaca for another 10 years. Because Polyphemus is the son of Poseidon, and now Poseidon knows who's injured his son, and Poseidon becomes Odysseus's sworn enemy, and he creates all these obstacles on his way home. So the point is, if Odysseus hadn't needed credit, if Odysseus hadn't bragged about what

he'd done, he would have gotten away with it, he would have gotten home safely. And so to me, this is a classic ego is the enemy type story. It's our desire for what Marks Reels would call the third thing, for needing recognition, for needing credit, for needing attention for what we've done that gets us into more trouble than we could possibly deal with. Look, it would be wonderful if life was easy. It would be wonderful if things went the way that we planned if we never ran into obstacles if the gods were always on our side. But that's not how it goes in life. It's not how it goes in the Odyssey either. One of my favorite poems is a poem about the Odyssey called Ithaca by C.P. Cavafee. And there's this part at the end where it says keep

Ithaca always in your mind because arriving there is what you're destined for. But don't hurry the journey. Better if it lasts for years. So you're old by the time you reach the island. Wealthy with all you've gained along the way, not expecting Ithaca to make you rich. It says, Ithaca gave you a marvelous journey, and without her you wouldn't have set out. She has nothing left to give you now. And then it ends, if you find her poor, Ithaca won't have fooled you, wise as you will have become so full of experience. You'll have understood by then what these Ithaca's mean. I guess that this is a long way of saying, like, the journey is the destination. It's what we learn along the

way. It's what we learn about ourselves. That is what we're actually after. When the Stokes talked about how the obstacle is the way, they didn't mean that you would always arrive at the Ithaca you hoped for. It might take longer than you expect. It might throw you wildly off course. You might end up somewhere very different than you ever would have liked to go. This is, of course, what happens to Zeno, who is traveling in the same Mediterranean as Odysseus, and he suffers this shipwreck. He washes up and out. He's not his destination. He loses one career, but he gains another. He becomes a philosopher. And later he would say, you know, I made a great fortune when I suffered a shipwreck, right?

Because it drove him to philosophy. So sometimes we think Ithaca, and this is Ithaca behind me, sometimes we think Ithaca is one thing, or we think Ithaca is supposed to be a certain way. But we don't know. We're not in control. The gods are in control. Fate is in control. Some timing we don't understand is in control. And so that's a good thing, or rather we can make it a good thing, in how we respond to it, and who we become as a result of it, and most of all, of course, what we learn from it. Everyone knows about the Sirens on the Rocks.

It's one of the most enduring images in all of literature. Beware the Sirens on the Rocks. The Sirens Call. Chris Hayes just wrote a book with that exact title, The Sirens Call. But what most people don't understand about the sirens, and I didn't even get myself at first, the Sirens aren't singing this song that is beautiful to everyone. No, they are singing a very specific song to each and every person. What their song is doing is telling people what they want to hear.

Every sailor's song is different. And I think this image applies very much to where we are today, and actually what Chris Hayes' book is about, where the algorithm is personalizing, where AI can generate incredibly specific things, where we can so easily fall into an information bubble. The sirens call, the sirens on the rocks, are this misinformation and disinformation, us being told the world is the way we want it to be, or the world is the opposite of the way we want it to be. And isn't that engaging and aggravating and incredibly triggering. And so we have to learn to resist this call, to resist the call of our apps, of our phones of the algorithm.

We have to know that people are trying to deceive us and activate us and aggravate us. In meditations, Mark Surrealus says that one of the things he learns from his philosophy to Jerusalem, Rousticus, was not to fall for every smooth talker. That's what the sirens are. The sirens are demagogues. The sirens are influencers. The sirens are the CEOs of tech companies that monetize and sell and package your engagement. And so, yeah, the sirens are this idea in the Mediterranean Sea almost 3,000 years ago. But they're also something incredibly modern and perennial. And that's why it's such a powerful image.

And that's why it's something we must remain aware of, we must be aware of even up and through today. Troy after 10 years of war. Does he have any idea what lies ahead? Does he have any idea what the gods have in store for him? Ten more years of obstacles and difficulties, 10 long years of travel, that he would come so close to the shores of his homeland, of his queen, of his young son. And then at the last minute, he'd be blown back again. He'd face storms and temptations, a Cyclops' deadly whirlpools, a six-headed monster, that he'd be held captive, that he'd suffer the wrath of Poseidon? Could he have known in those dark moments as he was suffering that

back home in Ithaca that his rivals were circling trying to take his kingdom and his wife? It's unimaginable. How did he get through it? How did he make it home despite it all? The Odyssey is a story about creativity, of course, and craft and leadership and discipline and courage. It's a story of warning against hubris. It's a story about the power of the gods and the traditions. But I think most of all, the Odyssey is a story about perseverance. Persistence was Odysseus in the Trojan War, right?

Trying everything till we finally get something that works till he chances upon the idea of the Trojan horse. Right? But 10 years of trials and tribulation of disappointments and mistakes without giving in, having to check your bearings every day, not just not inching closer to home, but getting further away, knowing that back at home there are all these problems laying in wait for you, enduring the punishments of the gods, doing everything it takes to make it back home. There's obviously at some point when persistence bleeds in to perseverance. Persistence is hammering away at some difficult problem.

Perseverance is something larger, something deeper, something more profound. It's the long game. It's not what happens in round one, but round after round after round, as you're burying people, as you're getting older, as you're getting more and more exhausted. That, to me, is the primary message of the Odyssey. Because life isn't about one obstacle. is about obstacle after obstacle after obstacle. And that's what Homer is showing us about Odysseus,

that we are all on our own kind of odyssey, right? Persistence is an action. Perseverance is a kind of will. One is energy, one is endurance, right? It's the famous line in the Tennyson poem, may weak by time and fate, but strong in will, to strive, to seek, to find, and not to yield. Not yielding.

That's what endurance is. I think about this famous summary of the teachings of Epictetus, he says, persist and resist, right? That's what Odysseus is doing in the Odyssey. I think people are too soft these days. We give up too easily. We tell ourselves that something is impossible because it's hard, because it's taking a long time, because vested interests are working against. But Odysseus doesn't do this.

He's stout-hearted. He's intense. He never gives up. He's always looking for a way. forward, he's willing to put up with setbacks that last for years. And even when he's retreating, even when he is blown wildly off course, there's always the final direction that he's never losing sight of. And that determination, that perseverance, that's what the Odyssey is about. And ultimately, that's what stoicism is about. When you're busy, when you work hard, when you push

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Indeed.com slash daily stoic. Terms and conditions apply. Hiring. Indeed is all you need. One of the most famous stories in the Odyssey has Odysseus lashing himself to the mast so that he won't be tempted by the sirens. The sirens being there on the rock, not just singing beautiful songs, but telling people what they want to hear. So Odysseus is tempted by this. He wants to hear it, but he doesn't want to crash. So he lashes himself to the mast. He plugs the ears of his men and he tells him, no matter how much I cry or struggle, don't let me go, don't listen to me until we are well past the sirens. Now, a couple of years ago, I was interviewing the behavioral psychologist Dr. Katie Milkman on the Daily Stoak podcast. We actually talked about this

very example because she said it was one of the first examples in ancient literature of a forced commitment. You know you're going to do a thing or you know you're not going to do a thing. And so you find a device that forces you to do it or prevents you from doing it, right? You don't by the Oreos or you lock the Oreos in a cabinet and you throw away the key. And actually this has become known as an Odysseus pact or a Ulysses pact. And that's when you make an agreement with someone or you create a device that in some way limits you from doing the thing that you might otherwise be inclined to do. And it's actually a pretty ingenious, if not rudimentary bit of basic psychology, right?

know you're tempted to eat something so you don't buy it or you lock it up or you give it away, right? I heard someone say that what you can do when you order an entree at a restaurant. You don't eat all of it is you tell the waiter, hey, I want you to cook this item, then box up half of it for me to take home and serve me the other half. That's the same version of this very ancient device, right? There's apps that block the internet on your phone. A bunch of writers I know use them. The idea being, I'm going to be tempted, and I don't want to be tempted, so I'm going to take away that temptation. I'll give you one in my own life. I don't have social media on my phone. It's on my wife's phone, because I know I shouldn't be using it, because I know it'll only

get me into trouble, it'll only distract me. So if I want to use it, I have to ask permission from someone else. And I can tell her, hey, don't give it to me today. Don't let me do it today. I know other people, their assistant controls the password. But the point is, the reason the Odyssey has endured is because of little examples like this. It is this strange epic poem about not being lured by these mythical monsters, and yet, at the same time, it's something imminently relatable to all of us.

Look, the Stoics talk a lot about discipline, and it's good to have it. But part of discipline is also knowing when your discipline is going to be overrun, when it is no match for the temptation you're going to be set against. I don't know, the first time, I read The Odyssey. I guess it was maybe in elementary school. Then we watched a made-for-tTV

movie. Then I read the Robert Fagull's translation in college. Then I read the Emily Wilson translation. Then I read the Emily Wilson translation to my son. And then we listened to a podcast about it. But each time that I hear the story of the Odyssey, I take something new out of it, which is this idea that we never step in the same river twice. The text is thousands of years old. It changes a little bit per each translation. But we change. change, what we're looking for changes, what we're able to comprehend changes, because we've gotten older, because we've experienced our own storms, our own difficulties, our own odyssey. And so that's why the text has endured for as long as it has, the story has

endured for as long as it has, because we're able to grow with it. It's able to be many things to many people, but also many things to each of us over the course of our lives. One of the best translators of the Odyssey is T.E. Lawrence. Now, what qualifies him to translate the Odyssey? Is it his education in the classics at Oxford, or is it his life experiences? He has this great quote where he says, you know, I have hunted wild boars. I have watched wild lions. He says, I have sailed the Aegean and sailed many ships.

He says, I have lived with pastoral people. I have built boats and I have killed many men. His point was that the Odyssey wasn't just this work of literature to him. It was a set of experiences, many of which he'd had, which of course informs his understanding of the text and his understanding of what the word mean in one language and another. We're told that with his philosophy teachers, Aryan and Rousticus, that Marcus Aurelius isn't content

to allow them to remain mere pen and ink philosophers, meaning he wanted them to have real-world experiences. He wanted them to be engaged in politics and life and business. And I think this is essential for all of us. We can't just remain with our books. We can't just remain with our stories. We have to be out there in the world. We have to be engaged in the world.

This is something that Plutarch talks about, too, who is both a writer and a politician and a priest at the Temple of Apollo. He would say that it might seem strange to some, but it was not so much by the words that he came to an understanding of things, but it was his experiences that helped him come to understand what the words mean. I think by traveling here, I have a deeper understanding of the Odyssey. Of course, having my own experiences leading people, having my own experiences with adversities and difficulties in my life,

having met some great men and women in my life, You come to understand the ideas in the odyssey. You come to understand the ideas in the text. You come to understand the ideas from the stoics in the philosophy better, which is why we have to remain a student of them, which is why we also have to remain a disciple of experience. We have to be going out and experiencing and learning new things and coming back to the text and, of course, bringing our texts to those very things.

So one of the more mysterious lines in the Odyssey is where Homer refers to the wine dark sea. The Odyssey is filled with beautiful images, the rosy finger dawn or a dawn with fingertips of rose. I've seen that. I get that. But the wine dark sea is perplexing not just to me. I've been all over Greece and I haven't seen one drop of ocean that looks like wine.

But to scholars too, you know, is that because he's blind? Is that because the ocean looked different back then? Or is it something a little bit more mind-blowing, which is like the way Homer saw colors is different than how we see colors. There's this German term in umwelt. Like what does the world look like to someone else, particularly like to animals? And what does it like to be a bat? What is it like to be a rat?

What is it like to be a Greek 2,500 years ago? We don't know. And so I've always been fascinated by that idea of people who describe and understand and see things very differently than we do. It's not that they're right or we're right or they're wrong and we're wrong. It's that we all see things very differently. This is one of the things Marcus talks about in meditations about how you want to really get inside people's minds and see things from their perspective.

What was it to them? Why did he describe it that way? I don't know exactly with Homer, but I've always found that. that to be very fascinating. The violence at the end of the Odyssey never sat super well with me. Odysseus gets home, he finds the suitors have overrun his house. He proves that he's Odysseus, and then what does he do? He hides all the weapons, and then he and his son, Telemachus, kill them.

He kills not just the hundreds of suitors, but all the servants who caborted with them. But it is shockingly violent and bloody and vicious. And I think fundamentally un-stoic. And we know this because a similar thing happens to Marcus, really is. Marcus has this chronic health condition, so rumors spread that the emperor has died. And his most trusted general, Evidius Cassius, names himself emperor, which puts Marcus his children and his wife in danger. It puts the future of the empire in danger.

I tell the story in the obstacles away. We know how a stoic would respond to this. And it's not with violence. Marcus does have to deal with it. But he tells his men that he wants to use this as an opportunity to teach future generations that there's a right way to deal even with civil wars. And Cassius is assassinated. We're actually told this happens over Marcus's objections, that he weeps when he's brought the head of his enemy because he has been deprived of the chance of granting him clemency. And then we're told that Marcus writes a letter to the Roman Senate and says that he wants everyone involved in this part.

He says, do not stain my rain in their blood. He says, may it never happen. There's this quote in meditations about how the best revenge is to not be like that. And we find that Odysseus, over the course of his travels and then his arrival home, he has hardened. He has lost a part of himself. He has become vicious. He has become brutal. He has become cruel.

He's become desensitized. And that's how sort of like that, he's able to order the killing of dozens and dozens of people. He stains his palace in blood. He stains his reign in blood. And so I've always thought of that scene. How could Odysseus have handled it differently? Obviously, you can't let people walk all over you. People have to be held accountable for their excesses and their abuses and in his case for enormous expenses they levied on the kingdom. But there was probably some punishment between letting them walk all over you with impunity and murdering them in what is effectively cold blood.

Odysseus is not a hero. He is a man to be pitied. He is tragic and flawed. His 20-year journey home, we find it inspiring, but we miss what he does almost the second he gets home, which is that he leaves again. He finally makes it back to Ithaca. He makes it here.

And what does he do? He almost immediately thereafter leaves to go on a series of raids to replenish his coffers. Odysseus is not a tragic figure because he is cursed by the gods. Odysseus is a tragic figure because he has cursed himself. He is endlessly restless. He can never, ever, ever be still. Actually, when you read the Tennyson poem, Ulysses, you get a sense of this.

He says, I cannot rest from travel. The whole poem is about him sort of handing the reins over to his son, Telemachus, because he's going to travel again. How dull it is to pause. To pause, he says, to make an end, to rest unburnished, not to shine in use. He is a machine. He is human doing, not human being. In the poem he says, you know, to my son who I leave this kingdom to, you're better than me,

you're wiser than me. He envies his son because his son can be still. His son can be king, not a wanderer. And the Stoics pitied these kinds of people, Seneca, most of all. We talked about how many people travel, not unlike the man who is flipping his pillow over and over again, trying to find the cool side as he tosses and turns and is unable to sleep. The Stoics understood that many people, when they travel, are traveling to flee themselves. Too many of us in our travels are running from something.

Too many of us in our ambition are hoping that on the other side of a hill, on the other side of some accomplishment, will finally feel good, will finally feel sated, but we won't. We are subjecting ourselves to the same torture that Odysseus subjected himself to. It's worse than what the gods can inflict on us. When Marcus Aurelius says that life is warfare and a journey far from home, he is describing, again, the tragic nature of his fate as the emperor. And that is the cautionary tale of the Odyssey, something we might miss in the first readings.

But as we go over it over and over again, we start to see that, yeah, we wouldn't want to trade places with Odysseus. In fact, we don't want to be anything like him. When was the Odyssey written? Was Homer blind? Is Homer the guy that wrote it? Did Odysseus exist? Is this place?

Ithaca, is this where it actually happened? Is this what it was all about? Seneca says it doesn't fucking matter. We get so obsessed with trivialities when it comes to literature and history. He says, it doesn't matter where these things happened to Odysseus. He says where he ran into these storms. He says, what matters is that we are running into our own storm, our own spiritual storms, that we have more trouble than Odysseus ever had to deal with.

And we should take from this a reminder that the purpose of history, the purpose of literature, is about moral questions. It's about how to be a good person. It's about how to deal with life. What matters is that we learn from Odysseus's hubris. We learn from Odysseus' cunning. We learn from Odysseus' determination and perseverance. We learn about his love of country.

We learn about his creativity. We learn how he outsmarts the sirens. We learn from the terrible dilemmas and betrayals that he makes along the way. That is the purpose of learning. That is the purpose of history. That's what a place like this teaches us, whether this is literally the place that it happened. Whether it literally happened or not doesn't matter.

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