The Daily Stoic - Go Back And Pick It Up Again | Is This the Life You Worked For?

Episode Date: October 8, 2026

Everyone has a book that changed their life. But how long has it been since you first read the book that hit you so hard?The new 10th Anniversary Edition of The Daily Stoic is out NOW! 👉 Grab your copy here: https://store.dailystoic.com/pages/the-daily-stoic-10🎟️ 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/dailyemail--Stop online threats before they become real-world attacks. Visit ironwall.com/DAILYSTOIC and request a free Risk Assessment to see exactly how exposed your executives are. Hosted on Acast. See acast.com/privacy for more information.

Welcome to the Daily Stoic podcast, designed to help bring those four key stoic virtues, courage, discipline, justice, and wisdom into the real world. Go back and pick it up again. Everyone has a book that changed their life, one that opened their eyes or taught them something, moved to them, challenged them. We know that this was Mark Srealis's reaction to Epictetus. Perhaps this was how you felt when you read Marks Ruelas for the first time. I know it was for me. But how long has it been since you read that book that first hit you? Now, think of everything that's happened then. All the other books you've read, the experiences you've had, things that have happened in the world, the lessons you've learned. How much have you grown? How much is your perspective shifted? In his great biography of Emerson, the Mind on Fire, Robert D. Richardson writes about a year of rereading that had a revitalizing effect on Emerson, enlivening his reading.

and sending him ranging over further afield. New readings overlapped old, he writes. Familiar books yielded fresh connections with the present, and books from one culture or era became newly applicable in another. This sort of cross-fertilization happened frequently for Emerson. This year in 1844, he gave it a name, Quasmo. Crossings or cross-breedings.

Its startling symbols for Emerson were the seashore and the taste of two metals in common. contact, our enlarged powers at the approach and the departure of a friend. He felt that these crossings or intersections most strongly perhaps in the experience of poetic creativeness, which is not found in staying at home nor yet in traveling, but in transitions from one to the other. And as he tried to court this crossroads experience, so he now tried to manage his whole life as to present as the most transitional surface possible. That word, quesmal, it itself came from a reread. Emerson is quoting a French philosopher who said that nature loves crossbreedings.

Growth, creativity, and insights emerge from this, from dynamic intersections, points where different ideas and experiences or influences converge and create something new, transformative, and vital. And this is why we cannot simply pick up a book once. It's why we have to revisit the books that shaped us again and again. It's crazy to me, but can you believe that It's been 10 years since the Daily Stoic came out. Think of the life you've lived since you first picked it up, what you've experienced, what you've learned, what's happened, how you've changed. For a decade now, Stoics all over the world have been reading those same pages, completing basically loops of the Daily Stoic getting something new from it each time. And the Daily Stoic 10th Anniversary Edition, which is out now, has been updated and informed by a decade of writing and reading about the Stoics.

more than 60 new translations. It's got new meditations, new stories, and expanded glossary, a bunch of awesome stuff. I think you'll really like it. Because again, we never step in the same river twice. That's why we must return again and again to the books that have impacted us. Revisit the Stoics. Revisit the books that changed your life. Revisit the works that have stood the test of time whose wisdom has endured across generations. Give them a chance to crossbreed with your ever-changing self and see what new wisdom emerges. And you know, normally updated editions, they just slap a new forward on the same book.

But I really wanted to go back and ask myself, hey, if I was doing this again, knowing everything I know now, what would I do? And that's what this new 10th anniversary edition of the Daily Stoic is. It's better. I'd like to think I'm a better writer. Certainly I understand the philosophy better. We added new stories.

We made corrections. As we said earlier, there's 60 new quotes. in there that weren't in the first edition. And there's new illustrations. Also, we totally redid and improved the leather edition, which is really made to stand the test of time. You can grab all that at dailysteoic.com slash DS10. I'll link to that in today's show notes.

Thanks to everyone who supported the book over the years. And I hope you like this new version. Makes a great gift. And these are signed numbered first editions. And, yeah, check it out. All right. Dailystoke.com slash DS10. One of the questions that we talk about with a lot of families is this idea of how do you define enough, right?

Whether that's in business, whether that's wealth, whether that's passing wealth to kids, right? That's a really big question for a lot of families. And so I'm curious how you think about it and how you define that mark. Yeah, there's the famous Kurt Vonnegut Joseph Heller story where they're at a party at some rich guy's house, which I've been to this. exact party many times. They're sort of talking about, you know, how this guy probably made more money than any of them had made in the totality of their book sales, despite them being, you know, two incredibly successful authors. And Joseph Heller says to Kurt Vonnegut, well, I have something this guy doesn't have. And he says, you know, what's that? He says enough. And it's a really powerful thing.

I think sometimes people might take that story to mean, okay, so he has enough. So he just doesn't care. Like, yes, he wrote Catch 22, but that's not the only book that he wrote. He had enough, but he wrote many books after this point. I think what Heller is saying, like, I'm not driven by money alone, and I'm not trying to get to some number or prove some point. And what I have noticed in a lot of successful people, and I've noticed it in a lot of my peers who are doing books, this is specifically what that story is about, is like the reward for succeeding at the thing that they love doing is that they don't get to do that thing anymore. You know, and so it's like someone really loves their chef, they love food. And then it's like, when was the last time they were in the kitchen? And it's like, no, because like the impulse is, well, we have one successful restaurant. So I got to scale it up and then I got to open another restaurant. And now of a sudden, all of their time is on phone calls and meetings and accounting stuff and marketing. And they don't actually get to do the thing that they like anymore. And like, I really love writing. That's why I decided to write books, right? Many books. Yeah. But no, no, I got into it because I like doing the thing, not because it was a means to an end, which was another thing. And so I think a lot about, like, how do I protect the time and the space?

So the reward for succeeding at the thing I love is that I get to do more of that thing. I get to do it in different ways. And there's obviously other things that I do. But I just don't want success to be a punishment. And so I think. The question is not just like enough, like what's your number? What is financial independence? But it's like if you get to some point of financial independence, well, what is that independence for? And how is it actually creating or facilitating what you like? And this is something I think the Stoics were talking about where they're like, who's in charge here? Like, yes, you have this company, but the company has you. You're running around from meeting to meeting, deal to deal. You don't see your kids. You can buy. everything but like the day that you want because that day is for you some point in the distant future when all of the when you sell when things slow down when you're older and the big thing

hovering over the stoics was like that is not guaranteed not just because in their time you know you could run afoul of the emperor and be exiled or killed but that's not guaranteed because markets could turn industries can turn and then also you know, you could die from a cut on your finger back then, right? Like today, we'd say, like, you'd get hit by a bus, right? So, like, the idea of, hey, I don't like my life now, or I do a lot of things I don't like to do now, so some point in the distant future, I'll be able to do whatever I want. Obviously, that's a version of a lie that everyone says, but I think the degree to which successful, wealthy, powerful people tell themselves this, even though they could have to be a

that right now is, I think, a really important, like, kind of philosophical thing to think about. Yeah. Yeah. I mean, I think it's one of those questions that takes a lot of work and reflection and probably constant work and thinking about how can I keep that front of mind. What's important? Like, you mentioned, what is that ideal day? What are you really striving for and having that front and center? Well, this is where all these virtues come in, right? So this decision of, like, having enough and then, you know, making sort of a countercultural, even transgressive decision to be like, I'm going to live and be this way. It's like, so first, let's go wisdom.

This is like self-awareness. This is understanding yourself, understanding what you want. This is discipline to be able to say no. Like sometimes that's the hardest thing to do in the world. It's also courage to be like, hey, I'm going to go in a different direction than everyone else. I'm going to do a thing that maybe not everyone understands or some of my peers laugh at me about or I'm just to have the courage to be like, hey, I'm good with this. I'm not going to, I'm not going to let it bother me that I'm at this point on this list and there are these people

above me. And then, and then also the justice of like, like, it's not all about you. And what's, where can you have more impact? Can you leave some for other people? You know, like, so all these virtues come in to these seemingly, you know, kind of modern questions of like, what am I here for what's enough, what should I be doing with my life. But these kind of timeless virtues, I think they always apply.