The Daily Stoic - When It’s Not How You Imagined | Seeking Out Shipwrecks

Episode Date: August 28, 2026

Fortune behaves however she pleases, as Seneca put it.🎶 Song lyrics: Lost Weekend - Phoebe Bridgers📚 Books: The Daily Stoic Lives of the Stoics 🎟️ 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. When it's not how you imagined. It wasn't supposed to go this way. This wasn't what you planned. This isn't fair. It happens. The question for the Stoics was, how are you going to react?

How are you going to handle disappointment, surprise, or injustice? I've been known to throw a tantrum, Phoebe Bridgers sings on her new album, when things are not the way I imagine them. It's actually a great line. Let me just play it real fast. That's what most of us do. Like children, we confuse our hopes and expectations with entitlements. We think that yelling or whining, resenting, or wishing will make something otherwise.

We think that we can undo what happened, that we can start it over or run it again. But that's not how it works. or how it ever will. We must remember that fortune behaves however she pleases, as Seneca put it. We have to be flexible and adaptable. And we must learn what Epictetus called the art of acquiescence. No tantrums, no fighting, just getting to work. Most leaders have a clear picture of how work is supposed to get done,

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how easily we can decide to rid ourselves of these things whenever it's necessary, never suffering the loss. That's from Seneca's Moral Letters, 87. This is an entry in the Daily Sto. 366 meditations on wisdom, perseverance, and the art of living from yours truly, Ryan Holiday, with my co-author and translator Steve Hanselman. You can get the book anywhere books are sold, including signed copies in the Daily Stoke store and our limited edition, leather-bound edition as well. Zeno, widely considered to be the founder of the School of Stoicism, was a merchant before he was a philosopher. On a voyage between islands and the Mediterranean, his ship sank along with its cargo. Zeno ended up in Athens, and while visiting a bookstore,

he was introduced to the philosophy of Socrates, and later an Athenian philosopher named Cretes. These influences drastically changed the course of his life, leading him to develop the thinking and principles that we now know as Stoicism. And according to the ancient biographer Diogenes, Zeno joke, now that I've suffered a shipwreck, I'm on a good journey. Or according to another account, you've done well fortune, driving me thus to philosophy. The Stoics weren't being hypocritical when they said we ought to act with a reverse clause or that even the most unfortunate events can turn out to be for the best. In fact, the entire philosophy is founded on that idea. You know, I tell this story at greater length in Lives of the Stoics, so I'll read you a chunk of that as well,

just because it's one of my favorite stories in all of Stoicism, and I think it's just so fitting. I write, The story of Stoicism begins fittingly in misfortune. On a fateful day late in the 4th century BC, the Phoenician merchant Zeno sent sail on the Mediterranean with cargo full of Tyrion purple dye. Zeno's family's trade was in one of the most valuable goods in the ancient world,

and as for many entrepreneurs, their business was on the line every day. No one knows what caused the wreck. Was it a storm, pirates, human air? Does it matter? Zeno lost everything, ship and cargo, in a time before insurance and venture capital. It was an irreplaceable fortune, and yet the unlucky merchant would later rejoice in his loss, claiming, I made a prosperous voyage when I suffered a shipwreck.

for it was the shipwreck that sent Zeno to Athens and on the path to creating what would become Stoic philosophy. Another fun wrinkle about this that I love is that, you know, he ends up in a bookstore. The bookseller is reading the works of Socrates, and this is what sends Zeno down its path. So I think there's a couple of things here. Zeno's quote is actually a little bit more about the idea of premeditoshia Malorum

about preparing for adversity. Maybe Zeno was prepared. Maybe he wasn't, again, and that his whole business was on the line, that he lost everything in this shipwreck, maybe suggests that perhaps he wasn't. But the idea that the worst possible thing, the thing you dread,

the thing you could not have imagined, the thing you think is the worst stroke of bad luck, turns out to be the pivot point of his entire life. Zeno, think about how many Tyrion die merchants there would have been in the ancient world, how many of their ships were coming into Athens, week in and week out, and think of how few of them we've even heard of.

I mean, have you even heard of Turing Purple? No, you haven't even heard of the country that Zeno's from, right? And so the irony is that the thing that he probably resented and was angry about and feared all of this turns out to be the only reason that we're even talking about him right now. And I think this is a good lesson that, you know, holds true in your own life, right? If you think about the worst things that have happened to you, the things that you dreaded, the things that you wanted, as time has passed,

you've seen how they've contributed to who you've become. That's not to say you would have chosen them. That's not to say that they weren't painful. And that's not to say that there wasn't more, in some cases, more downside than upside, but there was upside. And in that, we can make true what Zeno said, that we made a great fortune by suffering a shipwreck that perhaps from heartbreak,

came the love of your life or from a financial calamity came from some great injury, came a wonderful recovery, came a new way of doing things, from the heart attack, came an awakening about your health. The worst thing that happened to you can become something good. This is what the idea of the obstacle is the way is really about. And I just love so much that it's literally written into the story of stoicism that it is there at the beginning. it is there before the beginning.

In fact, it's there causing the beginning. And I think that can be true for all of us as well. So I'm not saying I hope your shipwrecks today. I'm just saying if your ship does wreck, let's turn it into a xenolike rising from the ashes.