The Daily Stoic - You Can’t Be Afraid To Lose It | Ask Daily Stoic

Episode Date: June 19, 2025

The Stoics remind you that the point of financial security is to feel secure. The point of plenty is to realize that you have enough. You can’t fear losing what you had–there was a time y...ou didn’t have it and you survived.💡The Wealthy Stoic: A Daily Stoic Guide to Being Rich, Happy, and Free explores how Stoic ideas can be applied to personal finance, wealth-building, financial mindset, and how it can help you overcome common financial obstacles and challenges👉 Get The Wealthy Stoic: A Daily Stoic Guide to Being Rich, Happy, and Free & all other Daily Stoic courses for FREE when you join Daily Stoic Life | dailystoic.com/life📚 Book Mentioned | Dying Every Day: Seneca at the Court of Nero by James Romm at The Painted Porch | https://www.thepaintedporch.com/📖 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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Starting point is 00:00:00 Wondery Plus subscribers can listen to the daily stoic early and ad free right now. Just join Wondery Plus in the Wondery app or on Apple Podcasts. Shopping local might seem like a tough cookie, but truthfully finding Ontario Made products is a piece of cake. That's why supportontariomade.ca exists. With over 17,000 products listed, everything from cars to cosmetics, it's never been easier to shop local and support Ontario manufacturers of all sizes. When you choose Ontario Made, you're supporting your neighbors, strengthening our economy,
Starting point is 00:00:31 and celebrating the incredible products Ontario sells with pride. Discover what's made right here. Visit supportontariomade.ca. Welcome to the Daily Stoic Podcast, where each day we bring you a stoic-inspired meditation designed to help you find strength and insight and wisdom into everyday life. Each one of these episodes is based on the 2,000-year-old philosophy that has guided some of 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.
Starting point is 00:01:20 For more, visit Dailystealhick.com. You can't be afraid to lose it. We wanna think that money will make us freer. We think it'll give us the power to say no to stuff we don't wanna do, to live how we wanna live, to take the risks that we want to take. But will it? How has that worked out for most people in history? This is the paradox of wealth.
Starting point is 00:01:53 Once we have it, instead of becoming free, we become obsessed with wanting to preserve our money, with not wanting to lose it, with wanting more of it. When Seneca said that slavery resides beneath marble and gold, he wasn't just talking about the time and cost and upkeep of nice stuff. He was talking about how easily we become prisoners of the status quo. That's why he would often experiment with what it was like to be poor, dressing in rags, going without food.
Starting point is 00:02:18 He wanted to be able to say, is this what you feared? He wanted to remind himself that losing what he had wasn't so bad. And it's good that he practiced this because Seneca did lose much of what he had when he left Nero's service. Although whether he should have gotten it in the first place is a different moral question, which James Rahm discuss in his amazing book, Dying Every Day. One ancient historian noted that Nero had trouble poisoning his former advisor because the meager natural diet that Seneca reverted to
Starting point is 00:02:45 presented so few opportunities. The Stoics remind you that the point of financial security is to feel secure. The point of plenty is to realize that you have enough. You shouldn't fear losing what you had. There was a time that you didn't have it and you survived. And besides, no one can ever take from you what you learned in order to get it. And this idea of enough, it's a simple idea. This idea of feeling secure from your financial security. This is simple enough, but of course it's very difficult. It requires certain amount of self-awareness,
Starting point is 00:03:16 certain amount of discipline. It requires, I think, some study and understanding and wisdom, and that's what we built the wealthy stoic on. The wealthy stoic, a daily stoic guide to being rich, free, and happy, I think built the wealthy stoic on. The wealthy stoic, a daily stoic guide to being rich, free and happy, I think is one of our best courses. It's a deep dive into what the stoics thought about money, how to be wealthy in every sense of the word,
Starting point is 00:03:34 not just to have a lot, but to feel like you have a lot, to feel like you have enough, to feel secure, to feel good, right? To feel good and secure even when you don't have much. It's nine weeks and to deep dive into the ambitions and motivations that fueled the stoic definition of wealth and success. How to find your own definition of wealth and success.
Starting point is 00:03:53 How stoics spent and saved money. What the stoics prized above money. Bunch of other stuff. It's great. I think you'll love it. There's deep dives and interviews with me and some great minds on money also, including the one and only Morgan Housel,
Starting point is 00:04:07 my friend, Cal Newport, Ali Webb, who's a hugely successful entrepreneur, bunch of awesome stuff. If you wanna tackle your relationship with money, we'll sign up for the Wealthy Stoic Daily Stoic Guide to Being Rich, Free and Happy. Go through the course at your leisure. It's dailystoic.com slash wealth.
Starting point is 00:04:23 Or if you're thinking about signing up for Daily Stoic Life, you can do that. Basically for the cost of this course, you get all our courses for free, plus a bunch of awesome, really cool benefits and more stuff for me. So go to dailystoiclife.com or dailystoic.com slash wealth.
Starting point is 00:04:41 Hey, it's Ryan. Welcome to a Thursday episode of the Daily Stoic Podcast. We talked about the Scipionic Circle before, right? This group of Stoics that would get together in ancient Rome and talk philosophy, talk life, talk business, talk politics. And the Scipionic Circle, you hear about it from Plutarch, you hear about it from Cicero. It was sort of one of the first, you could call it a mastermind group. And obviously that's a thing now.
Starting point is 00:05:07 I've belonged to a couple. I've spoken at countless ones. I've been bringing you some excerpts of a talk I gave back in February. 10 guys from all over the country get together four times a year. They bring out a speaker. This time they all flew in Austin.
Starting point is 00:05:22 I drove out to Lake Buchanan. There's like five lakes in a row going out from Austin. And it was a very cold day. As I said, I swam in Barton Springs that morning. It was like 28 degrees and I was freezing. So you might hear some of the shivers or the chattering of my teeth in here because it took me quite a long time
Starting point is 00:05:38 to get my body temperature up. But otherwise, this is me answering their questions. And if you are looking for a little Sipionic Circle, that's what we try to do in Daily Stoic Life. You can join us at DailyStoicLife.com. You get all our Daily Stoic courses, you get Q&As, you get a bunch of other awesome bonuses. We've been doing it a really long time.
Starting point is 00:05:59 It's one of my favorite things. I get a bunch out of it and I think you will as well. I was talking to Molly Bloom one time, you know, the Aaron Sorkin movie Molly's Game. She was the poker entrepreneur. Anyways, we were talking about someone we both knew who we always see him in, you know, pictures of private jets and they're almost whatever. And I go like, I know what their business is, that math doesn't like, I know what that costs. This isn't like private jet money. And she goes, one thing I learned that you should never forget is that that person could
Starting point is 00:06:35 just be a criminal. And I was like, oh, yeah, in our world, right, most you're like, oh, you're on the up and up. If they're beating me, it must just because they're better or smarter or got lucky or whatever. Her peek into the underbelly of a very different world, you're like, oh, they could just not be paying their taxes or they could just be, you know, it could be a fraud. The Ponzi scheme guy from the thing or whatever.
Starting point is 00:06:55 Exactly. And so I just sometimes like when I find myself being jealous, even if it's not true, I just go like, they could be a criminal. Like, you don't know. That's the justice. And then I don't have to think about it, right? Then I'm, all of a sudden, you're not comparing yourself to that person. So that was always very helpful to me.
Starting point is 00:07:10 How does AI first, being a writer, an author, are you implementing anything, certain technologies in your processes? I'm thinking a lot about this actually. The book that I'm just finishing, I tell the story at the beginning, there's this sort of wealthy Roman who, you know, he wants to be smart,
Starting point is 00:07:28 he wants to impress people, and he's got money so he could, you know, go back to school, he could learn a bunch of stuff, he could study, put in the work. Instead, he hires this group of slaves, each one who's very smart, with a specific sort of ancient writer. So he picks one who knows Homer,
Starting point is 00:07:44 one who knows Euripides, one who knows Aeschylus, and then they follow him around and like at dinner parties and stuff, when he needs to say something, they whisper in his ear what he should say. And he thinks he's kind of getting away with it. Everyone thinks he's so smart. And a friend comes up to him and he says,
Starting point is 00:08:01 you know, this is such a lovely party, you're so smart. Have you ever thought about becoming a wrestler? Wrestling being the sort of main sport for the Greeks and the Romans. And he goes, why would I become a wrestler? I'm an old man. And then his friend looks at him and goes, yeah, but your slaves are still young.
Starting point is 00:08:16 And Seneca's point is that like wisdom, like all things that takes work and that you never get it by chance. There's no secret, there's no shortcut, there's no magical thing that just gets you what you want. I think we could say safely that our kids, their life is gonna be defined by how good they are at using AI, right?
Starting point is 00:08:37 So that's my next question. So I'm thinking a lot about how do I teach them, like it comes down to what they call prompt engineering. Like how good are you at getting what you want from this thing? Like it's a tool, it's magic, but how good are you at summoning the magic, I think is that. So I, I've been fooling around with my kids a lot. Like one of the things they did, we've done this for a year or two now is
Starting point is 00:08:58 like, if they want to color something, we like work with AI to make something cool for them that we print out and they color or, you know, if they want to color something, we work with AI to make something cool. For them to color. Then we print out and they color. Or if they want to hear a story, we ask it. They're putting in the inputs and then getting the outputs. Or they're like, what did that look like? And we're like, well, let's have it do it. Go through it.
Starting point is 00:09:16 Think through it. And then going, OK, hey, the reason this isn't what you want it to be is because your question is unclear. And how do you refine it? And so kind of teaching them how to not just be comfortable using it, but good at using it. In your chat with Jay Shetty, you talked about ambition as an addiction. How do you keep your drive in check so it doesn't burn you out or blind? And you talked about it a little bit with your writing on this.
Starting point is 00:09:45 I just try to be driven about stuff that I control. So if your drive is to be the number one of this or to be recognized as that or to beat this or that, you better hope it goes the way that you want it to go or you're gonna be unhappy. But if your ambition is tied, this is basically the core of Stoes.
Starting point is 00:10:08 If you're more rooted in the parts of it you control, then no one can prevent you from getting that thing, or fewer things can prevent you from getting that thing. So it's like, if my ambition is to write a really great book, it's still gonna be super hard hard and there's no guarantee, but I control my own destiny more than if my goal is to win the Nobel Prize for Literature. Hey, it's Ryan.
Starting point is 00:10:37 Thank you for listening to the Daily Stoic podcast. I just wanted to say we so appreciate it. We love serving you. It's amazing to us that over 30 million people have downloaded these episodes in the couple of years we've been doing it. It's an honor. Please spread the word, tell people about it. And this isn't to sell anything. I just wanted to say thank you. If you like The Daily Stoic and thanks for listening, you can listen early and ad free right now by joining Wondery Plus in the Wondery app or on Apple podcasts.
Starting point is 00:11:15 Prime members can listen ad free on Amazon Music. And before you go, would you tell us about yourself by filling out a short survey on Wondery.com. As night falls, she must use all her wits to survive. Don't miss this heart-stopping thriller. Wait until dark at the Shaw. For tickets, go to shawfest.com.

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