Don’t Underestimate This | Ask DS

We don’t know a lot about Seneca’s friend Lucilius. From Seneca’s letters though, we get the sense that he, like many of us, was often overwhelmed by his responsibilities. He was a Roman knight. He was the Governor of Sicily. He owned a country villa in Ardea. We can assume he had friends and family vying for his time too.--And in today's Ask Daily Stoic, Ryan speaks and answers questions for Signal Advisors on Stillness is the Key, Challenging people to do one thing each day that positively moves your life forward, and more stoic wisdom to a group of independent financial advisers. ⏳ You can view our entire Memento Mori Collection at dailystoic.com/mm✉️ Sign up for the Daily Stoic email: https://dailystoic.com/dailyemail🏛 Check out the Daily Stoic Store for Stoic inspired products, signed books, and more.📱 Follow us: Instagram, Twitter, YouTube, TikTok, FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. 📢 Share | ⚙️ Manage Subscription

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

• 0:03Ryan Holiday?

  Welcome to the Daily Stoic Podcast, where each day we read a passage of ancient wisdom designed to help you in your everyday life. While on Thursdays, we not only read the daily meditation, but we answer some questions from listeners and fellow Stoics who are trying to apply this philosophy just as you are. Some of these come from my talks. Some of these come from Zoom sessions that we do with Daily Stoic Life members or as part of the challenges. Some of them are from interactions I have on the street when there happened to be someone there recording. But thank you for listening and we hope this is of use to you. Don't underestimate this. We don't know a lot about Seneca's friend Lucilius. From Seneca's letters, though,

• 0:48Ryan Holiday?

  we get the sense that he, like many of us, was often overwhelmed by his responsibilities. He was a Romanite. He was the governor of Sicily. He owned a large country villa. We can assume that he had friends and family vying for his time soon. One of the best pieces of advice from Seneca was about how to manage it all. "Each day," he told Lucilius, "acquire something that will fortify you against poverty, against death, indeed, against other misfortunes as well. Just make sure to do one thing each day," Seneca was saying, "that positively moves your life forward. That's it. It's not a lot, but it adds up." That's the secret also of those who are highly productive. On the Daily Stoic Podcast, the author Paul Kix talked about how he wrote The Saboteur,

• 1:33Ryan Holiday?

  an incredible book optioned by Steven Spielberg while he was working full-time at ESPN and tending to two newborns. It worked for Seneca. It worked for Paul. It'll work for you. Just try to make a little progress each day. Don't underestimate the power of small but consistent contributions to your work, to your relationships, to your family. Small things, as Zeno said, are truly no small thing because they add up.

• 2:01Ryan Holiday?

  And look, if you're trying to be a writer and you've struggled to make that time, you want to break through like Paul Kix did, like all writers, including Seneca, including myself, have struggled to do, you might be interested, actually, in this school new course that Paul has been running. It's called the Storytelling You. People are staring at the blank page like you. They've taken his course, they've taken the Storytelling You, and they've gone onto land in Dream Publications, they've inked big book deals, they've even won National Magazine Awards. It's not a magic bullet, but it can make you better if you do the work, day by day, step by step. Actually, someone from the Daily Stoic team, Kristin, who is editing today's email, took the course. She really liked it, and they've been raving about it. So Paul's extending a special offer to Daily

• 2:44Ryan Holiday?

  Stoic subscribers. He and his team will work with you. Until you earn back double your investment in the Storytelling You, you can click the link in today's show notes, or just go to dailystoic.com/kix, and it'll redirect you over to the page. I recommend it. I love Paul's stuff. He did a nice profile of me for ESPN The Magazine a couple of years ago. He's been a great podcast guest, and he's a big fan of the Stoics. So I think that you'll find some Stoic advice in the course as well. Check out the Storytelling You at dailystoic.com/kix, K-I-X, or just click the link in today's show notes.

• 3:28Speaker 01

  I had a grind of a speaking schedule a couple of months ago. I was in like three states in three days. I got in very late. I didn't know exactly where I was going. I just sort of go where the agent told the driver to go, and I show up, and I'm at the lodge at Torrey Pines in La Jolla, California, one of the most beautiful places I have seen in my travels. And got up early. I went for this amazing run down to the water, looking out over these bluffs. Running, I watched this guy pull a stingray out of the ocean, which is pretty nuts. And FaceTime with my kids. I'm showing him as he's reeling it in.

• 4:10Speaker 01

  Just a beautiful morning and then I worked, I had lunch while I was reading, swam some laps in the pool and then I went and gave a talk. I was talking to Signal Advisors. It was a, it's a company that works with independent financial advisors. They wanted me to talk to, talk about the obstacle is the way, which I'm always happy to do. And then I answered some questions at the end. Let's just say I was in a good headspace. I talked a little bit about stillness during the talk and I had, after all the craziness, after the travel, had just a great day, vibing in the right headspace, performed well, I felt, answered some questions and then I got on a plane and then I made it home before it was too late and got back into the rhythm here

• 4:55Speaker 01

  at the office. And so I'm bringing you my questions. Thanks to Signal Advisors for having me out. Anytime someone wants to bring me to the lodge at Torrey Pines, I am game. And in the meantime, here's my answers to some questions on Stoicism and other topics for you to check out.

• 5:14Speaker 02

  Yes, the idea that we're going to do a little Q and A and we'll take some Q and A from the crowd.

• 5:18Speaker 01

  Cool.

• 5:19Speaker 02

  As I had mentioned, I've been a long time fan and read so much of what you've done. So I know a lot about your past, you know, the fact that you've decided to drop out of college and you're a director of marketing in American Apparel and then went on to be Robert Greene's research assistant. And I'm curious, you know, we talked a lot today about how success is in a straight line.

• 5:39Speaker 01

  Sure.

• 5:41Speaker 02

  And I'm curious about, you know, did you always know you wanted to be a writer? And how did you kind of will that into existence? Like, what was the path that took you to where you are today?

• 5:50Speaker 01

  Yeah, that's a great question. I do think what sometimes the mistake we make is we look at people that end up at a place and then we look at the path that led them there and we ignore all

• 6:01Ryan Holiday?

  Other paths that they considered taking, all the other things they were doing simultaneously. We go, okay, they got from here to there. And obviously, it was all meticulously planned. And then we try to reverse engineer it from there. So, you know, when I, when people look at my career and they go, okay, he had this marketing thing. And then he switched to ancient philosophy. Obviously, that must have been a dramatic turn. Like, it didn't go that way at all. I, I knew I wanted to be a writer for a long time. That was one of the things I wanted to do with my life. Then I got really interested in marketing for a while. I had a fascinating and cool career in that, um, that world. Meanwhile, I was informed by these philosophical ideas that we're talking about. But I didn't know if I could or how I would write about them.

• 6:46Ryan Holiday?

  And then, um, I wrote three books while I was still, uh, at American Apparel. Then I wrote several more while I had my own marketing company. And so, you know, in retrospect, it seems clear, like, one leads to another, leads, leads to another. But in fact, doing a lot of things sort of concurrently. And then it's only with time that, you know, and success in one field or another, that you sort of winnow things down. And so, I'm, uh, you know, just like an investor has a diversified portfolio. You want to have a bunch of different things that you're doing. Obviously, mastery requires a certain amount of concentration. But at the same time, you know, as long as these different things that you're doing are informing the main thing, um, making you better in that way.

• 7:30Ryan Holiday?

  That's kind of how I think about it. And we, and we should be really clear that we, really careful that we don't just sort of buy the narratives of certain people. That it's like, I set out to do this and that's how it happened. And it's like, more often than not, it was a total surprise to them. And the clarity and certainty about it was later, right? Even the decision to drop out of college, I remember, and I was like 51, 49 about it, right? And it, in retrospect, it worked out. But if it hadn't worked out, I would have just gone back to school. We'd be talking about how I took a semester off or something, right?

• 8:04Speaker 02

  Yeah, yeah, super interesting. I'm curious, you know, sometimes the idea to change something or make a certain decision, you know, it comes out of like frustration or a moment where, you know, you really feel like you need to make a change.

• 8:20Ryan Holiday?

  Mm-hmm.

• 8:21Speaker 02

  But I'm curious about making decisions when things are going great. Like, you know, when you're research assistant for Robert Greene.

• 8:25Ryan Holiday?

  Yeah.

• 8:26Speaker 02

  You know, big mentors, like, how do you decide to... You're in that situation. How do you decide, okay, it's time for me now to part ways with this moment in time?

• 8:33Ryan Holiday?

  Yeah. No, that is, that is a good point, right? Oftentimes, if you're well-paid for something, if something's going well, people are recognizing you for something, it feels like suicide, like career suicide. It feels crazy to be like, I'm gonna stop doing this thing.

• 8:50Speaker 02

  Right.

• 8:50Ryan Holiday?

  But, you know, if you have a sense of what you want your life to be, where you're trying to end up, you know, what's actually important to you, those things become, I think, a little bit less important, right? So I think sometimes, because people don't know what they want, they most specifically don't know what they want, like their days to look like or their life to look like, it's very hard for them to make decisions, right? Should I keep doing this? Should I stop doing this? Should I say yes to this? And this is also very hard, this is particularly hard when you are successful, you have a lot of inbound, right? And those decisions are, let's say, financially lucrative, right?

• 9:30Ryan Holiday?

  So if you don't know what you want, and someone's offering you money to do this, and not money, like, this thing is risky, there's no money in it, you just sort of end up defaulting or going towards that, and that can end up taking you very far from, like, where you deep down want to end up, but you haven't spent a lot of time thinking about it.

• 9:53Speaker 02

  Really answer those questions?

• 9:53Ryan Holiday?

  Yeah, I, I, I think about lots of sort of offers that I've gotten to do things, you know...

• 10:01Ryan Holiday?

  Things that would have been cool, things that have been cool on a resume or on a biography. But I go like, if I had said yes to this, all these other doors would have been closed. Right. And all these other things that are so important to me day to day wouldn't be possible or would have gone away. And so, you know, not just, not just doing things because A pays more than B, or not just doing things because lots of people you know are more excited about A than B. Right. Like, um, when I decided to write this book about philosophy, pretty much no one was excited about it but me. I, it was meaningful to me. It was the direction I wanted to go.

• 10:39Speaker 02

  Your first book?

• 10:40Ryan Holiday?

  Uh, this is maybe my third book.

• 10:41Speaker 02

  Okay. Well, your first book about philosophy?

• 10:43Ryan Holiday?

  Yes.

• 10:43Speaker 02

  First time you wrote about philosophy, everyone was like, what are you doing? Why?

• 10:46Ryan Holiday?

  Yes, exactly. My publisher later told me that they, the only reason they even gave me an offer was they hoped either one, it would be so low that I would be insulted and not accept it, or that I would do it, it wouldn't work, and then I would go back to the other thing.

• 10:59Speaker 02

  Be in the marketing, so go back to being the marketing guy.

• 11:01Ryan Holiday?

  Exactly. But I knew that wasn't what I wanted to do day in and day out. That wasn't what I wanted to talk about, wasn't what I, I, I just felt like if I didn't do that, someone else would do it. And I felt like this other stuff that I wanted to do, I felt like maybe I was the only person that could do it.

• 11:17Speaker 02

  Why obscure Roman philosophy? Like, how did, how did that, like, you heard that somewhere or you read a book and you're like, this is the thing that I'm going to dedicate a lot of my life to? Like, why Stoicism?

• 11:27Ryan Holiday?

  I mean, I think when you find the thing that like turns on a light for you, or that like really gets you going, that is a rare and special thing. And so, when I first read the Stoics, I was like, what? You know, where has this been? Uh, I mean, I was, I was pretty young, so it's not like it was, it had to be so amazing. Like, I was probably easily impressed to a certain degree, but it, it very much was like what I was looking for. I hadn't found or seen anything like it and really still haven't. And so, you know, it did something for me and I, I sort of was motivated by the idea of. Doing that for other people. And so, you know, when you find that thing, I'm not saying it has to be the only thing that you do.

• 12:06Ryan Holiday?

  But when you find that the thing that sort of only you can do, that's a, that's a pretty powerful, powerful thing. Or the, the way that-

• 12:15Speaker 02

  Yeah, only, only you can do. How do you, how do you think about that? Because like, you know, other people can write about Stoic philosophy.

• 12:20Ryan Holiday?

  Yeah.

• 12:20Speaker 02

  Like, how do you, how do you think about?

• 12:22Ryan Holiday?

  I, I've been thinking about this. So like, every person is by definition totally unique, right? Your, your combination of DNA has never existed. The moment in time that you were born has never existed before. You know, the experience that you've had has never existed before. So you are, you know, a black swan of black swans. You know, you're totally unprecedented in all of human history. There will never be anything like you again. And then what do we do is we do what everyone else is doing, right? Um, we just make ourselves, we dress like other people, we talk the same way as other people. We, oh, you gotta go to this college like everyone else, then you gotta do this. And then, um, I, I, I wrote a book a couple of years ago about billionaire Peter Thiel,

• 13:05Ryan Holiday?

  who's this sort of unique character who I don't agree with on many, many things, but is clearly a sort of a brilliant mind. He's the first investor in Facebook, founded PayPal and Palantir. Anyways, he has this line in his book, Zero to One, and he says, um, I think about this all the time. He says, "Competition is for losers." And the idea is that if you are competing with other people, one of you will win and the other will lose. If you are doing something for which you are, only you are suited to do, you're the only one doing it, you by definition win, right? And so do you want to be better or do you want to be the only, right? And I think when I, um, yes, other people have written about Stoic philosophy.

• 13:49Ryan Holiday?

  Clearly other people write books, but like- When my book came out, people were like, what is this? Right? It was like my publisher didn't quite know what to do with it. The market didn't quite know what to do with it. I leaned into what I was interested in, what lit me up. And I tried to do something that if I didn't do, it wouldn't have happened. And so I think that's what you want to think about within the market or industry that you're in. It's not like you have to go be this sort of crazy weirdo, but you have to be, you know, unique inside the space that you are in.

• 14:23Speaker 02

  I know exactly. I mean, and for what it's worth, I mean, you don't need me to tell you this, but I mean, when I, if I read your book, if your name was on the front cover, I would know it's you.

• 14:30Ryan Holiday?

  Oh, that's awesome. Yeah, that's what I'm trying to do.

• 14:31Speaker 02

  So, okay, yeah, you're hitting the nail on the head with that one.

• 14:33Ryan Holiday?

  Yes.

• 14:34Speaker 02

  You know, but I think, I think that's true about like artists, like even like I think about, this is kind of a funny one, but it's like when I hear someone on the radio and I know who it is just by this, like hearing their voice, like I feel like that's why they're famous.

• 14:45Ryan Holiday?

  Yes.

• 14:46Speaker 02

  That's why people like, that's why their music takes off. Like Lil Wayne, you know when Lil Wayne's rapping in a song.

• 14:51Ryan Holiday?

  That's why they call him the alien, right? He seems like he came here from somewhere else. He's fully formed and he's just different than anything that's ever existed. And that's, that's what you want. Um, actually I'm wearing Iron Maiden socks right now. The band Iron Maiden has this great quote, the, the lead singer of Iron Maiden, which is a band maybe most people in this room haven't heard of or you heard of is like this band from a long time ago. And they sold a hundred million albums, they drew stadiums all over the world, even though they're never on the radio, they're never in pop culture. But the, the lead singer had this quote that I think about, he says, um, he's like, you can only plow one field at a time. And his point is we have our fields and that's what we're in charge of cultivating. And, um, and, uh, you know, I don't care, he says, I don't care what the other farmers are doing.

• 15:35Ryan Holiday?

  And I, I heard this story once about Iron Maiden's manager. Somebody came up to him and he said, you know, like you're, you're one of my heroes in the, in the music business. And he said, I'm not in the music business. And I was like, what? He said, I'm in the fucking Iron Maiden business.

• 15:51Ryan Holiday?

  And the idea is like, you're not in this space, right? You're in your own space that only you are in. And that is why you stand out. That's why you get media attention. That's why you can charge your own prices, right? If you are doing what everyone else is doing, then it is a commodity and it is a race to the bottom to see who can charge the least amount. But if you're the only one doing it, you can charge whatever you want.