This Is How The Weak Beat The Strong | Ask Daily Stoic

You may not have a lot of money. Or powerful connections. Or even superior genetics. Does this mean you’re at a disadvantage?📚 The Four Stoic Virtues: Justice, Temperance, Wisdom, Courage, are timeless keys to living your best life. The Daily Stoic is releasing a limited collector’s edition set of all four books signed and numbered, with a title page identifying these books as part of the only printing of this series. PLUS we're including one of the notecards Ryan used while writing the series. Pre-order the Limited Edition Stoic Virtues Series Today! | https://store.dailystoic.com/pages/stoic-virtues📖 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 Facebook 📢 Share | ⚙️ Manage Subscription

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:05Ryan Holiday?

  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, 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, visit DailyStoic.com.

• 0:56Ryan Holiday?

  This is how the weak beat the strong. You may not have a lot of money or powerful connections or even superior genetics. Does this mean you're at a disadvantage? That you're screwed? Maybe that you're at a disadvantage? Yes. Does it mean you're screwed? No, because there is a great leveler out there. The famous Princeton basketball coach Pete Carroll would tell his young athletes that his father came from a province in Spain and worked for years in the open hearth that Bethlehem Steel Company. Every day before he left for work, Carroll would say he would remind my sister and I how important it was to be smart. In this life, he would say,

• 1:39Ryan Holiday?

  "The big, strong guys are always taking from the smaller, weaker guys." But, he said, "The smart take from the strong." It's simple, fatherly wisdom. You've got to use your brain. It is the secret weapon of underdogs everywhere, always available and always free. Think of David deciding to use his sling in the fight against Goliath. Think of the Stoic opposition, outmatched and outgunned by the many tyrants of their time, and yet they managed to get inside the heads. Of these tyrants, they managed to win in the long battle. History. Think of the wealthiest and most powerful people of antiquity, sitting at the feet of Epictetus, a former slave.

• 2:24Ryan Holiday?

  Think of Stockdale and the Hanoi Hilton getting into long debates with his captors about Marxism and winning. Life is a thinking person's game. If you want to beat the strong, the rich and the powerful, get smart. The greatest educational fallacy Stockdale would say is that you can get it without stress. The road to wisdom, to living of the philosophical life is not an easy one. It takes work. That's my argument in the new book, Wisdom Takes Work. It is the work of our life. And if you want to know how to do that work better, if you want to learn from some of the smartest people who have ever lived, I would love for you to preorder it. The book is out on October 21st, but you can preorder signed and numbered first editions.

• 3:09Ryan Holiday?

  You can actually get a special edition set of all four books in the series, Courage, Discipline, Just Wisdom. And it would mean so much to me if you could preorder it. We only did 1,500 of those. They're almost sold out. You can grab those, that collector set at dailystoic.com/stoicvirtues. I'll link to that in today's show notes as well. And I'd really appreciate it. Enjoy and keep doing the work, folks.

• 3:49Ryan Holiday?

  Hey, it's Ryan. Welcome to another episode of the Daily Stoic Podcast. So my sort of routine when I do talks is I usually end up getting there the night before, go for a run in the morning before the talk. And then I go down and I do my thing. It's not always that way. Back in June, it was the same day talk. So I flew to Virginia Beach, had maybe like an hour and a half to run, grab something to eat, change, go down, do the talk. So I ran along the boardwalk there in Virginia Beach, somewhere I'd never been. And then I gave a talk to a group you wouldn't think would be an audience for an obscure school of ancient philosophy, but it was. It's the International Right of Way Association's annual conference.

• 4:32Ryan Holiday?

  I guess running along a boardwalk is fitting. It was a beautiful, you know, sort of public work that the kinds of engineers and architects and administrators at something like the International Right of Ways Association would be involved in. So I did a big talk to the group. It was about 1,000 people. Then afterwards, we did sort of a 30-minute meet and greet Q and A session. Sometimes at these talks, it's kind of like a little, it's like a post-game conference. So anyways, I did that. And that's what I wanted to bring you today. This is the folks at the International Right of Way Association asking me some questions afterwards. And hopefully, these are matched with some of your questions. And I thought it was really interesting. So thanks to them for having me out.

• 5:17Ryan Holiday?

  And then I'm gonna go give a talk now, in a few minutes, downstairs in my hotel. Let's get into it.

• 5:29Speaker 01

  Somebody did ask me, like, oh, you're gonna meet Brian Holiday. And you're like, what are you gonna ask him? And I will tell you that my one question is, can you come, like, live with me for 16? I can ask you a thousand questions. Because there is no one question.

• 5:43Ryan Holiday?

  Okay.

• 5:44Speaker 01

  So if somebody else has one, have that. But thank you again, and thank you, Brian.

• 5:48Ryan Holiday?

  Sure.

• 5:50Speaker 01

  So, ask the question.

• 5:52Speaker 02

  I don't know what to say. I'm like, we've read a bunch of your books. And I'll say that we say to each other all the time when something happens, it's tricky. Like, hey, Obstacle's the Way. We remind each other constantly of that.

• 6:00Ryan Holiday?

  Sure.

• 6:01Speaker 02

  And you're in Austin?

• 6:02Ryan Holiday?

  Yes.

• 6:02Speaker 02

  Okay, I live in forward.

• 6:03Ryan Holiday?

  Oh, okay. Cool.

• 6:05Speaker 02

  Yeah, I saw the Vass Troop stuff. And I'm like, oh, I know all the spots.

• 6:08Ryan Holiday?

  Yeah, yeah, yeah.

• 6:09Speaker 03

  My question is, I started with Obstacle's the Way, and went through the list. And then you came out with Conspiracy. Where did you get that idea from?

• 6:16Speaker 01

  Oh.

• 6:18Ryan Holiday?

  Yeah, I mean, kind of similar to the idea in The Obstacle's the Way. Someone was sort of telling me about this crazy story. It's about this billionaire who was trying to destroy a media outlet. And... It was very different than all my other books. And so it seemed like it would be a challenge to do, which it was. I mean, it was like twenty thousand.

• 6:38Speaker 03

  A lot of research.

• 6:39Ryan Holiday?

  Yeah, and so it's like, oh, I'd love to just try something very different. And, and even if it didn't work, I would just be better for having tried to do it in a different way. It's actually funny, there's a line in Meditations remarks to this, it's talking about, um, trying to hold the reins of his horse with his non-dominant hand. Like, he's just trying to do it in a way that he doesn't normally do it. And that was kind of how that came about, is just, uh, I loved reading those kind of books.

• 7:08Speaker 03

  Yeah.

• 7:08Ryan Holiday?

  Uh, and I wanted to see if I could write one. And so, I mean, the book is.

• 7:12Speaker 03

  You did.

• 7:13Ryan Holiday?

  Thank you, I'm very proud of it for, for the reasons that I know I got better for having done it. And then, um, yeah, so I don't know if I'll do another one, but.

• 7:22Speaker 03

  It's kind of like when Malcolm Gladwell came out with The Bomber Mafia. It's like, this isn't really the same what he normally does.

• 7:29Ryan Holiday?

  And I think he's really messed with the sort of me, the, the, the line between book and audiobook and ra-, you know, he's like kind of messing with the, the medium, which I think is what you, at, at some point, you should be kind of pushing the boundaries of what you do, otherwise you're just doing the same thing.

• 7:47Speaker 03

  Right.

• 7:47Ryan Holiday?

  Over and over again.

• 7:48Speaker 03

  Conspiracy is very different, I don't know if y'all have read it, than The Obstacle is the Way, Still Misses the Key, and He Goes the Enemy, it's, it's about Hulk Hogan, right?

• 7:56Speaker 01

  Yeah.

• 7:56Speaker 03

  And how this billionaire decided to bring Gawker to its knees.

• 8:00Ryan Holiday?

  Yeah.

• 8:01Speaker 03

  And it involved Hulk Hogan and things we won't talk about in this company.

• 8:04Ryan Holiday?

  Yeah.

• 8:05Speaker 01

  Yeah, it was fascinating, also, it was very well written. How did you get in the conversation with it?

• 8:14Ryan Holiday?

  Yeah, I mean, I think, so someone recommended that I read the Stoics, and I did, and, and I think what was so striking, which I think is what happens whenever you read something great, is you're like, I didn't know this was out there, you know? Um, and, and I think when you're reading, you know, books from two thousand years ago, but it feels like it could be written about like the moment you're in right now, that's like a really magical thing. And I, I think what's always been striking to me about the Stoics, yeah, sometimes they mention certain things, you go, okay, that's very much a product of a time and a place, but the rest of it feels like it could be just as much about the digital age. And just sort of the timelessness of, I think that's what really struck me.

• 8:56Ryan Holiday?

  Yeah, it's, you know, they call philosophy the great conversation. And I think that's what it is. It's these ideas from thousands of years ago, plus our perspective now. And even though those texts say the same, you know, what we're looking for in them or the problems we're dealing with now, we find new ways of interpreting and reinterpreting.

• 9:16Speaker 01

  I've always loved writing. And she gave me this talk about being true to your word. I remember that story about somebody being taken captive.

• 9:28Ryan Holiday?

  Oh, yeah, Regulus?

• 9:29Speaker 01

  Yes, yeah, and I love that story. So you were saying, can you tell me?

• 9:33Ryan Holiday?

  There's a Roman general who's caught prisoner. And then he's sent back to negotiate peace on a diplomatic mission. But they make him promise that if it fails, he'll come back. And so he goes and he says like, hey, I don't think we should make peace. I think they're losing. And so the Romans think it's a good advice, whatever. He goes back because he's like, I gave my word that I would come back. And they torture him to that. And his point, it doesn't matter. You give your word when you want to fall through. You gotta fall through even when you don't want to. Yeah. And so it's sort of a famous story about like, let the Romans keep their word.

• 10:07Speaker 01

  Yeah, I just thought, and that was why I thought he would be good for our ministry, like how important that is for us. Yeah.

• 10:18Ryan Holiday?

  Promise something you can't deliver or go back on your word? Well, yeah, there's also this like, you know, is it, he's not legally obligated to come back. You know, it's like a negotiation with the enemy. But he's like, no, I said I would do it, so I'm gonna do it. And I mean, I think it's a fascinating sort of ethical quandary too. Like, what do you owe? What, does he actually need to? But his point was, you gotta be able to trust. If a Roman says something in a negotiation. Can they trust it? And you just realize like the whole even like the international system is set up on these different, you know, precedents and norms and then it's easy in one individual instance to be like, well, it's bad for me. So I'm not going to follow it.

• 11:01Speaker 01

  Right.

• 11:01Ryan Holiday?

  But then that creates sort of a wicked feedback loop. So yeah, that's what that's about.

• 11:06Speaker 01

  Well, thank you again.

• 11:07Ryan Holiday?

  Of course. I'm just gonna ask, so what do you journal? Yeah. That is definitely one thing that a lot of people do. Yes. I don't do. Okay. So how do you use that? What do you, what do you find is your, inhibits you from doing it? Just too busy or you don't like it or you don't know? Not a priority or yeah, I just don't know, I guess maybe what to. Well, I think sometimes people overthink it. They're like, what is, do I have to write everything I did today? Or do I have to like, do your diary and spill your, you know, it's like.

• 11:34Speaker 01

  I had to watch your breakfast.

• 11:35Ryan Holiday?

  Yeah, I, I, I tend to think it's like, whatever works for you is what you should do. I like to, there's, there are a bunch of different journals that have prompts that are a nice way to get sort of build a habit. Cause there's like a question you're answering and then you're like, oh, that's all I'm doing. Like I have one journal that I like that's, it's called the one line a day journal. And it has one line and five slots and you keep it for five years. So you write one thing, I usually write like something about the day that just happened. But like, so the first year's cool, second year's cool, third year's really cool, fourth and fifth years. You're like, oh, here's where I was on June first, 2024, 23, 22, 21. And so.

• 12:18Speaker 01

  Okay, so you get one sentence.

• 12:19Ryan Holiday?

  One sentence, but all on one page for that date. Yeah. So I would just, I would just like, at this point, they're no longer just like, oh, here's a blank journal, fill it up. There's like lots of different kinds when people, that's sort of technology that's been developed. If you think about it that way. But like journaling is one of those things, I think that at some future point, you're going to wish you had done. Yeah. And so you just, I would just find some way to do it. And, and I think if you're like, I've had to do it every day for this long. Then you're making it a chore. It should just be like, when I feel like it, I'd spend some time putting some thoughts down on paper. Not so much for me right now, but for future me or for who I am after I do it. Like to me, the, I don't, I don't usually go back through my journals other than like the one line a day.

• 13:04Ryan Holiday?

  Cause you're looking, you've seen it each day for five years. But it's more like when I get it down on the page. Then it's not in here.

• 13:12Speaker 01

  That's, yeah, that is why, that's the biggest benefit I find from it. And a lot of times I'll get in bed and not, and then like, I gotta get up, I gotta get up.

• 13:21Ryan Holiday?

  It calms you down.

• 13:22Speaker 01

  Yeah.

• 13:22Ryan Holiday?

  And you're like, you put it down and you're like, that feels pretty ridiculous now that I've written it.

• 13:27Speaker 01

  Right.

• 13:27Ryan Holiday?

  You know what I mean? Or like, I'm, by writing it down, I don't have to say it to this person.

• 13:38Ryan Holiday?

  Hey, it's Ryan. 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.