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Ryan Holiday
I'm picking up my kids from school in a little bit, and then we're going to go to Whole Foods. They want to eat sushi. I got to get groceries. We play a game where they try to throw as much stuff into the cart as they can get away with. And then I see what I can get away with sneaking out of the cart. But this is kind of our weekly routine. We go to Whole Foods all the time, and when we're not physically near a Whole Foods like in Austin, we get it delivered. I'm a big fan of Whole Foods. Actually, in my talk in Austin just the other day, I talked about John Mackey, the founder of Whole Foods, because I love Whole Foods commitment to high standards for their ingredients and sourcing, how they treat their vendors, the dyes they keep out of their food, the preservatives they keep out of their food, most of the staples in our pantry in our freezer, as well as the fruit that my kids go through like maniacs. It all comes not just from Whole Foods, but from their house brand365 by Whole Foods Market. You can enjoy so many ways to save on cozy fall meals at Whole Foods Market. I'll see you there. Look, I think it takes most of our mental power and willpower just to decide to work out right, to go, hey, I'm going to do that thing. I don't want to do it. It's going to be hard, but I'm going to do it. So then when you get down to doing it, you don't necessarily have all the energy and focus that you need to, like, do it right. And that's where today's sponsor comes in. Because tonal provides the convenience of a full gym and the guidance of a personal trainer anytime at home with one sleek system. The whole thing designed to reduce your mental load, Tonal is the ultimate strength training system, helping you focus less on workout planning and more on getting results. Tonal does a quick assessment, sets the optimal weight for every move, and then it adjusts it in these little increments to help you get stronger so you're always challenged. And you can choose from a variety of expert LED workouts to keep you coming back for more. Right now, tonal is offering our listeners 200 off your Tonal purchase with promo code TDS. Just head over to Tonal.com and use promo code TDS for 200 bucks off your purchase. That's Tonal.com promo code TDS for $200 off.
Steve Hanselman
Morning, Zoe. Got donuts. Jeff Bridges. Why are you still living above our garage. Well I dig the mattress and I want to be in a T mobile commercial like you teach me so Dana oh no, I'm not really prepared. I couldn't possibly AT T Mobile get the new iPhone 17 Pro on them. It's designed to be the most powerful iPhone yet and has the ultimate pro camera system.
Ryan Holiday
Wow.
Steve Hanselman
Impressive. Let me try. T Mobile is the best place to.
Ryan Holiday
Get iPhone 17 Pro because they've got the best network.
Steve Hanselman
Nice. Jeffrey, you heard them.
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Steve Hanselman
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Ryan Holiday
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Ryan Holiday
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Ryan Holiday
256 gigs $1,099.99 A new line minimum $100 plus a month Plan with auto, PayPal, taxes and FE Best mobile network in the US based on analysis by Ooklove Speed Test Intelligence data 1H 2025 Visit t mobile.com 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 2000-year-old flag 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. For more, visit Dailystoic.com foreign Hey, it's Ryan. Welcome to another episode of the Daily Stoic Podcast. There's basically one person to thank for this. All existing. Not me. Although I guess I deserve some of the credit. Not my wife who's kept me sane and supported me and believed in me and indulged me all these years. Although again, she deserves a lot of credit. I could thank Ms. Cars and Mr. Del Ordo, my sophomore English and US history teachers who I think in the afterword of the new book Wisdom Takes Work, because they were the first ones who saw something in me as a writer and a thinker about history and encouraged me. Obviously, they deserve a lot of credit and I'm in their debt. Robert Greene, of course, my mentor who taught me how to write, taught me how to think, taught me how to do this professionally. Lots and lots of credit to all of them, but specifically Daily Stoic, the podcast, the email, the book, it all traces back to a conversation I had with Steve Hanselman, my agent. He sold my first book. Trust me, I'm lying. He sold the Obstacle Is the Way, sold my book on growth hacking. But it was Steve who came to me at some point in the middle of those books and said, hey, I published this book called the Daily Drucker when he was an editor at HarperCollins. And he said, I think you should do a book about Stoic philosophy that is a page a day called the Daily Stoic. I said, steve, I don't know about that. I mean, I've read the Daily Trucker, but who reads these page a day books? I just read it from COVID to cover because that's like how I used to only think about books. And he said, you don't understand. These are a way to live with the thinking of someone, not just for a year, but over and over and over again. People dip in and dip out of it, and it becomes this massive and very accessible entry point into something. And I understood that because I had bought the Daily Drucker because someone had recommended Peter Drucker's writings. But he didn't have, like one book that was like the main one. And I didn't want to get it wrong. So I was like, oh, this is kind of like a greatest hits album. And so Steve said, look, I think you should do this book. And he's like, I think it will be your best selling book ever. And I said, well, that seems like something an agent would say that doesn't seem like it would actually be true. But he turned out to be right. But before that, I said, steve, look, there's kind of a problem. Whose translations are we going to use? The individual quotes might be fair use, but you can't put together a whole collection of quotes from some. The Gregory Hayes translation of Meditations or, you know, this. The Penguin Random House edition of Seneca's Letters. And he said, no, no, no, I understand. I'll do the translations. And I said, how? And he said, I went to Harvard Divinity School. I know both Latin and Greek, and I'll do the translations. And I said, were you holding out on me? I didn't know you could do this. So anyways, Steve is the reason that the Daily Stoic exists. That's why his name is on the COVID of the book. He's been a wonderful supporter, patron, co writer, collaborator, sounding board advocate for my works over the years. It's my John Landau, if you will. And it's been lovely and wonderful, and I owe him A lot and I appreciate all of it. So I thought as a bonus episode I would bring you Steve and I talking about this series, which Steve also sold, believed in more than anyone else, helped sell it for an amount that was life changing for me and my family. I used the advance from the four book series to buy the bookstore which I am talking to you from. So he has been an enabler in all the best ways to me over the years and I can't wait for you to hear from him. We are sold out of the collector's set of all four virtues. Courageous calling, discipline is destiny, Right thing and right now. But you can buy a set of all four of them signed and we can do that. We will be bringing a box set out at some point as well. Enjoy this conversation with Steve and I. It would mean so much to me if you could pre order the new book Wisdom Takes Work or any of the books in this series. I'm really proud of this one. I can't wait for it to be in your hands. They should be shipping all over the world right now. You can grab it right now on audible or ebooks, all that. It is up and available and I'm pumped to bring it to you. Talk soon. Thanks. It's been six years. That seems like an insane amount of time.
Steve Hanselman
Yeah, I remember you were out on a family hike first, called me with the idea for the series and we both got so excited about it. And who knew, six years later we're about to launch the last one.
Ryan Holiday
What do you remember thinking about the idea?
Steve Hanselman
You know, I thought it was coming at a great time. Obviously the whole movement around the daily Stoic and the sort of growing community, you know, and a lot of people sort of hungry for more information. And of course, if you really want to dive deep with the Stoics, you've got to get into the virtues and into the whole subject of building character.
Ryan Holiday
What I remember is that obstacle, ego and stillness had sort of come about accidentally. So this was the first time that I'd thought more than one, one little thing in advance.
Steve Hanselman
Yeah, the. The virtues, of course, are central to Stoicism and they were hotly debated from Zeno, you know, all the way through. But the four cardinal virtues were one of the great gifts of Stoicism to the whole Western culture. And of course, Christianity had its own riff on those.
Ryan Holiday
Do you think they came to them independently or do you think they took them directly from Zeno? Because when I was just in Greece, I was thinking about this. You know, St. Paul starts at the Stoa and makes his way up to the hill where he gives his speech at the Acropolis. So there was obviously some intermingling.
Steve Hanselman
Sure. I mean, they were. Paul was a student of the philosophers. He was there on Mars Hill, on the Areopagus, to debate the philosophers, even quoting the Stoics, you know, to the audience.
Ryan Holiday
Yeah. Doesn't he mention or alludes to Cleanthes in that speech or someone.
Steve Hanselman
Right, Cleanthes, him to Zeus. Some say it's Heratus who preceded the poet, who preceded Clean out these. But, you know, was very Stoic inflected. This idea that we all have a share of the divine in us, that, you know, we descend from this greater. From this greater power. He thought he was speaking to a friendly audience. And in fact, as Christian tradition has it, you know, he converted one of the elders there. The Areopagites, Dionysius, the Areopagite, Really? Who is to this day the patron saint of Athens.
Ryan Holiday
Yeah. I have to admit, I thought that the cardinal virtues. I just thought cardinal meant like a religious cardinal. Obviously. Not having spoken Latin, I didn't get that it comes from Cardos. I just assumed that the virtues were primarily Christian in basis, not that they preceded it.
Steve Hanselman
Well, you know, the Christianity sort of came up in vigorous debate with the philosophers. And you can see the love that the Christian fathers had, you know, for the various philosophers. Sometimes I think Jerome said he worried that, you know, he loved Cicero more. More than anything else. So. And of course, Cicero was one of the best students of. Of Stoicism, and much of what we know about the tradition he preserved.
Ryan Holiday
So maybe it's more of a throwback, but this is kind of an old school discussion to be having with your book agent. You know, we should be talking, like, deal points and stuff and.
Steve Hanselman
Yeah, well, that's what's been fun about working on all these books with you, is that, you know, it's something that we spend a lot of time reading and reflecting on and, you know, as the point of. Of your new book, Wisdom Takes Work. It's all in the application, the consistent, the persistent, the constant reapplication and refinement of the ideas. It's like Epictetus said. He was always admonishing his students who were bragging about how much Chrysippus they knew.
Ryan Holiday
Yes.
Steve Hanselman
And he was like, you know, I could care less how much you know or how much you've read. It's like, how are you applying it?
Ryan Holiday
Well, my favorite. Doesn't he joke that he was talking to a student who was Bragging about having read all of the works of Chrysippus, Chrysippus being a particularly dense writer. And Epictetus says something like 705 books, right? Yeah. He says, you know, if Chrysippus was a better writer, you'd have less to brag about.
Steve Hanselman
Exactly. And of course, he had his critics, too, foremost of which were the Epicureans, who constantly berated Chrysippus as cribbing and quoting everyone else.
Ryan Holiday
But, you know, why get that criticism, too?
Steve Hanselman
Well, it's feel like an artist, Right. You're going to learn from the best, and, you know, you can't be afraid of stealing from the best. You can, if you can. Actually, if you're a musician, if you can get it under your fingers, you've really done something.
Ryan Holiday
Well, I also think, like, look, if I could say it better myself, I would have, you know, and there is this struggle, I think, when you. When you get some of these quotes from the Stoics, you go, I'm not sure I could say it better. And if I tried, I'd really just be plagiarizing. You know, like, I could put this in my own words and act like I came up with it, but I didn't. You know, Seneca or Marx, Aurelius or Epictetus or Cleanthes or whomever. They just boiled it down to the essence of what it is, and they said it about as well as you can say it. And I've got no problem just saying that they said it.
Steve Hanselman
Yeah, well, they're varied sources and they all kind of put a different inflection on it. And you can learn so much just from pouring through it. And what I love about your book here is that you've really done that hard work of going through it, but trying to make it relevant and opening the book with the. With a quote from Epicurus I thought was brilliant. Let no one be slow to seek wisdom when he is young, nor weary in the search thereof when he has grown old, for no age is too early or too late for the health of the soul.
Ryan Holiday
Well, let me ask you, when I came to you with the idea for the series, where did you think it would go? Because I was looking at the proposal the other day, and there's some things I got. You know, I sort of predicted exactly where it would go, and then others I didn't. I'm forgetting what I titled the last book in the series, but it wasn't Wisdom Takes Work, for sure. How did you think the series would go? And then, let's talk More about this one specifically. But I'm curious what your vision was for it and then how you think it went.
Steve Hanselman
Well, you know, when you're dealing with the four virtues, it's like, where to start.
Ryan Holiday
Yes.
Steve Hanselman
And as I said, you know, it's such a debate within Stoicism. I mean, they just fought with each other. You know, are they different? Are they all one?
Ryan Holiday
Where does one begin and the other end? That's really the tricky part of the whole thing.
Steve Hanselman
Exactly. And they, you know, all the Stoics saw them as different sort of angles on knowledge, different forms of knowledge, but how they interrelated and, you know, even how to teach them was something they debated fiercely. And as you know, in the early days, you had Aristo, who was Zeno's great critic, who Zeno was, you know, calling a babbler and telling him to shut up, you know, half the time. Zeno, in fact, had a defender among the students who sided with him, wrote books like, sort of praising Aristo, who said that there was only one virtue and it was wisdom.
Ryan Holiday
Yeah.
Steve Hanselman
Forget about all the rest of it. So, you know, it's. Where to begin with. It was a hard question. But I thought, you know, at the beginning, starting with courage was the right place to begin, and it really. I think it resonated with the times.
Ryan Holiday
The interesting thing is that courage seems to be where. When they list the virtues, courage is always first. Then they sometimes shake up the order of the others, but courage always seemed to be first. But the interesting thing about writing courage is that almost all of the examples of courage seem to involve justice in some way. Like, there's very few examples of courage isolated from justice. And so there was this kind of problem to, like, logistical problem with the book, which is that you don't want to use up all the justice stories in the courage book. That was tricky. But it also strikes me that, like, certainly all the physical examples of courage involve justice in some way, but then most of the examples of moral courage involve wisdom in some way. Because what you're doing is seeing either through or further than everyone else. Right. You're having to, like, if you think about, like, someone who's not racist in a time of racism or not, not sexist in a time of sexism. Obviously, part of this is just a. A sort of moral sense of right and wrong.
Steve Hanselman
But.
Ryan Holiday
But really there's some sort of fundamental insight at the. The. The core of that worldview where you are able to see something clearly that while everyone else around you has their judgment clouded by Prejudice or, you know, close mindedness or whatever. I think the idea of the interrelatedness of the virtues, I think that seems obvious to most people, but it actually is a logistical problem when you're writing this series of books, because you can only write them one at a time, right?
Steve Hanselman
Well, I think, you know, in the case of courage, I think in any of the virtues, wisdom is always playing a role. It's like a caretaker, it's a caretaking role. And, you know, we talked about it when the book came out. I mean, just the history of Roman Stoicism, its involvement in the political leadership. There was kind of a great crisis emerging, you know, within the Roman office holders. You know, there was such an impulse toward gaining the office, going out, showing your courage in battle so that you could gain all this windfall of profits, you know, from the provinces, part of which of course came back to Rome. But many of these guys were, you know, just lining their own pockets. And it was, you know, during that period when the Stoics were really reflecting and people like Panaetius who were engaged with people like Polybius, you know, they were, they were really saying, you know, there's something missing here in the way we're talking about courage. We're missing the social dimension, we're missing the larger sense. And so they started bringing forward this idea of greatness, of soul, Megalosukiya, which brought in the social dimension not only courage for myself and what I can get, but courage for the greater good. And that became a very big topic from that period on. And I think it's a case where, you know, wisdom was coming to the aid of this sort of wooden form of courage that was passing for civic virtue, you know, during the time.
Ryan Holiday
Thanks to Toyota trucks for sponsoring this episode. When I bought my ranch in 2015 out here in Bastow County, I drove my car about halfway down the dirt road that we live on, thought, this isn't going to work. Stopped, parked it, walked the rest of the way home, borrowed my wife's car, drove into Austin and bought a truck. What I bought was a Toyota Tacoma. And this truck wasn't just transportation getting me to and from my house. It unlocked a whole different style of living for us. Not just on the ranch, but in our little Texas towns. There were places I could go now that I couldn't go before, especially out here in the piney forests, through the fields and on the unpaved roads like the one that I lived in. We got to go deep into the hill country's wild beauty. We've driven all the way out to East Texas. We've driven it across the country. And by we, I mean not just my wife, but both my kids, who I drove home from the hospital in that truck. Toyota trucks are built for those who understand that the best adventures happen when you're willing to veer off course. Because you never know when you'll end up on a Toyota Adventure Detour. And of course, this is stoicism too, because every detour, every obstacle is an opportunity. But it's helpful if you can handle the difficulty inherent in that. If you've got the resilience and the right companion to make it wherever the road takes you, discover your uncharted territory. Learn more@toyota.com Trucks Adventure detours by the time you know you need someone new on your team, you're already behind, right? You don't need to hire someone tomorrow, you need to hire somebody new yesterday. So how can you find amazing candidates fast? Easy. Just use Indeed. When it comes to hiring, Indeed is all you need. Stop struggling to get your job post seen. Indeed's Sponsored Jobs helps you stand out and hire fast. And with Sponsored Jobs, your post jumps to the top of the page for relevant candidates so you can reach the people you want faster. According to Indeed data, Sponsored Jobs post directly on Indeed have 45% more applicants than non sponsored jobs. And plus, with Indeed sponsored Jobs, there's no monthly subscription, no long term contracts, and you only pay for results. People were hired on Indeed while you were listening to this. That's how fast it is. There's no need to wait any longer. Speed up your hiring right now with Indeed and listeners of this show will get $75 sponsored job credit to get your jobs more visibility@ Indeed.com DailyStoke just go to Indeed.com DailyStoke right now and support the show by saying you heard about Indeed on this podcast. Indeed.comDailySTOIC Terms and Conditions apply. Indeed is all you need. Courage for what? Like holding the office for what? Being brave in battle for what? That's the sort of lingering question. And obviously justice informs that. The interrelatedness between justice and wisdom I found really interesting. You know, I have a couple of justice stories about sort of going and seeing how the the other side lives. You know, Theodore Roosevelt deciding to go down to the tenements in the Lower east side and you know, seeing how these people lived. Like on the one hand, that's this sort of moral obligation, but it's also at some other level, like curiosity, right? Like you can't Know that something's wrong if you're not interested in finding out about how things are. And so there's this sort of interrelatedness and then the courage he has to buck his party to sort of be involved in a social justice issue instead of a sort of laissez faire capitalistic stance, which is what the Republican Party had stood for at that time. Again, they're all kind of related. Right. And one informs the other, which forms the other, which in turn sort of brings you back to where you started. It's this kind of feedback loop. But wisdom has to be the curiosity, the open mindedness, the desire to learn, the ability to hear. You know, it's. It's all of these things that I think are unfortunately not necessarily the default setting for most people intellectually.
Steve Hanselman
Yeah. And I think, you know, too often people think of wisdom, it becomes like this lofty thing. And the Stoics were very insistent that when they talked about it, they used the word phronesis, which was practical wisdom. Yes. It wasn't this theoretical thing for the sage or somebody sitting on a cloud. It was something we had to engage in, everything that we do. In fact, Arius Didymus, one of the two Stoic advisors to Octavian when he became Augustus, he defined it phronesis, practical wisdom as that which deals with appropriate acts. So it was this constant idea that we're on the line. It's our choice, our decision, our moral character that's facing the test. We have to ask ourselves what is an appropriate action? And so this practical knowledge, it was like a street intelligence. In fact, the translator of Arius Didymus, that's actually the term he uses, knowledge, intelligence. Yeah. And Arius Didymus defined this practical wisdom as containing all these things you were just talking about. Soundness of judgment, circumspection, things like shrewdness, like the idea of being shrewd, of being sensible, of having a sound aim, Soundness of aim. Things like ingenuity.
Ryan Holiday
Yeah.
Steve Hanselman
Were part of justice. I mean ingenuity. I mean the word for E.U. maconian, this sort of ability to skillfully fashion what is needed on the spot. Marcus Aurelius even had his own term for this, hupex hiresis. It was his reserve clause that he wasn't always going to think he had the right decision in hand or the right conception of how things should go. He was willing to step back and reconsider if necessary.
Ryan Holiday
Well, that's the famous passage about if there's brambles in the path, go around if it's if it's bitter, throw it out. I think people sometimes think wisdom and justice is this kind of purity.
Steve Hanselman
It was the furthest thing from rote learning. It was not rote learning. It wasn't like you've got this bag of shiny, pristine virtues and you're just going to somehow magically pull them out and use them in the right way every time. Life is messy, problems occur along the way and the sort of working out of a virtuous life is much more involved.
Ryan Holiday
Yeah. I think sometimes people resent the fact that the Stoics don't kind of lay it all out, you know, do this, don't do that. Like, they don't really define the terms that well. And so there actually is quite a bit of work you have to do. And it's not relativism and it's not this sort of ends justify the means necessarily, but it is this idea of like, look, I told you what the virtues are. Courage, you know, self discipline, justice and wisdom. Figure it out. You know, like, figure it out. It's on you. That's the work of it.
Steve Hanselman
Yeah. You've got a great chapter in part two of the book, the Change youe Mind chapter. Yeah, I just. I really loved a quote there. I'm gonna read it. I wrote it down. I was just going through the book again. Cause I got it yesterday.
Ryan Holiday
I know, mine came too. I was very excited right after we talked about. I got the UK edition first and then the US edition after.
Steve Hanselman
I haven't seen the UK yet, but see, I've got this great couple lines in there that wisdom is the ability to go through life ready to change your mind. Doesn't mean we abandon our values because they're inconvenient. But our thinking is supposed to evolve, we're supposed to grow. New things are going to come to light. Feedback follows belief in action. We should create new beliefs and actions.
Ryan Holiday
Yeah, I mean, that's what I think is interesting in Meditations is how often Marcus Aurelius talks about taking correction, taking feedback, making mistakes. This is a guy, for all intensive purposes, who is believed to be a God. I mean, he is infallible. His word can literally mean life or death. He can do whatever you want. He's definitely considered to be smarter and more informed than most people. He certainly is better educated than almost everyone. So it's pretty remarkable to see in his private journal just how much he's talking about being wrong and changing his mind.
Steve Hanselman
That reproof from the truth has never hurt anyone.
Ryan Holiday
Yeah. And we know he means this too, right? He's not just paying lip service, because we have in some of his letters, which I talk about in the book, you know, he gets this. He gets two letters on the same day from Fronto, his rhetoric teacher. And he's well past being instructed by this guy. I mean, he's an adult. But he gets two letters from one of his old teachers, one of which is telling him how great he is and how happy and proud he is of him. And then the other one is a pretty set of extensive notes sent unsolicited about one of Marcus's speeches. And Marcus writes back, you know, I have to say, the second letter I appreciated much more than the first. He. Because I have to imagine that very few people are pulling the Emperor of Rome aside and saying, you know, that wasn't one of your best speeches. Here's a bunch of things you could have done differently or didn't you learn better? You know, it's really only this old teacher that can. Can lay it out for him like that. And I think he, you know, it says something about what he tried to remain, that he stayed open to that for sure.
Steve Hanselman
Yeah, it's definitely a resounding feature of his personality. The humility, the constantly going over the decisions he's made and. And being open to the fact that he may have missed it.
Ryan Holiday
And look, I relate to that because this thing you and I have been talking about, and it's for. For people who want to know kind of the inside of the development of this book a little bit, one of the interesting things about, you know, even where I was in 2019, when I sold the series, and then as the books have continued to sell, and then as I got to this fourth book, one of the things that. That I've sort of subtly noticed is, you know, you get less and less notes. Now, some of that is. Some of that is good, right, because it means there's less obvious things to fix. But I found it somewhat vexing that when the stakes are highest, you're actually getting the least amount of feedback and editing and accountability, right? It's like you can think, who. Who needs more correction than the Emperor of Rome, right? And then who needs the most edits? You don't need the edits on your first book when no one is reading. You need the. The most rigorous edits on your. I don't even know what number this is. But, you know, I need the edits more now, especially out of the gate, because there's a bigger audience, right? And I Know, I've been. And I think we addressed it well in this book is Julia, your wife gave an excellent round of very rigorous edits that I had to really shake out because I wasn't getting them elsewhere. But this idea of, like, how do you remain a humble practitioner of what you do? How do you actively seek out criticism and feedback? You would think that that would just come along for the ride, but it doesn't. It's something you have to sort of actively cultivate.
Steve Hanselman
No. Well, it's, you know, you've got such a disciplined process that has been honed over such a long period of time that the quality has, you know, definitely increased book by book. And I think we're what, through 15 now? That's a remarkable statement in and of itself right there.
Ryan Holiday
Yeah, but, but, but they, they sort. It's like. It's like at the beginning of your career, you want as little interference and as much creative freedom as possible. That's what you think you're working towards, right? Like, there's that episode of Curb youb Enthusiasm where Larry is selling the show to Netflix and he just goes, just remember, don't give me any fucking notes. You know, he's like, no notes. And that is kind of the dream, because there, there can be kind of piddly interference where people are second guessing you or trying to make it. I mean, I. I definitely felt that on some of the earlier books, conspiracy most of all, where you're like, I know what I'm trying to do here. I need people to get on board with the vision that I have. But then, you know, then you kind of get that deference that comes along with experience and credibility and success in a weird way that deference can impair you. Because now no one's telling you that it's too long. No one's telling you where your argument is, is weak. No one's pushing you to tighten or improve. And so I did kind of feel on this one. I'm glad I waited for it to be the last book in this series because in some ways I think it was the hardest. But I also felt like to. For each one to surpass the last, I had to sort of really work to get those notes, which isn't a part of the process I expected.
Steve Hanselman
Yeah, it's great to be here, standing at the end of that process now and to know that you've done such a fabulous job with it. In the third section of the book, you're talking about Lincoln and Pleanthes.
Ryan Holiday
Yeah.
Steve Hanselman
And it's just Interesting the way you brought those two people together because, like, they're this powerful combination of learning slowly and being methodical. And like, you know, in Lincoln's case, you know, sort of having this cabinet of rivals and, you know, constantly challenging himself. You know, in Cleanthes case, he would often talk to himself as the. As if he was a ignorant, an old man, you know, without any wisdom. But that sort of, you know, seeking to challenge yourself always, you know, it. It does elevate the product. And in the case of both, you know. Well, certainly in Cleanthe's case, as they said about him, he never forgot what he learned. The. The gains that he made, the improvements that he made were completely internalized as a result.
Ryan Holiday
Isn't it. Isn't it interesting how certain sort of metaphors or analogies persist? Like both the Stoics and the Buddhists talk about that idea of, like a bowl or a cup of water that's got some silt in it and you've got to let it settle, to see through it. And then. Yeah, to have. Have Zeno compare Cleanthes to a waxen tablet that you carve it in and then it hardens. That was how his mind works. And then, you know. Yeah. 2,500 years later, to have Lincoln compare his mind to. You carve something in it, and it's hard to do, but once it's carved there, it never goes away. You wonder if that's just kind of a naturally occurring insight, or is it actually something that Zeno threw out there 25 centuries ago that is just remaining in constant use? Like. Like at some point, every cliche was said by someone as an original insight. And I. Yeah, I loved that. That both of them were kind of described the same way.
Steve Hanselman
Yeah. I mean, you know, it's like, are you doing something for the performance value of it, or are you doing it to really get it?
Ryan Holiday
Yes.
Steve Hanselman
You know, I think it's kind of what it comes down to. You know, Marcus, in the sixth book, he talks about that there's only one prize, only one prize that the exertions of teaching and education are about, and that's that we should have self respect for our own mind and prize it so that we'll be in better harmony with ourselves and the universe. And I think, you know, in the case of Lincoln, in the case of Cleanthes, that they got it. They knew what the prize was. They weren't doing all the things they were doing for external validation. To be the smartest guy in the room, to, you know, be acclaimed for knowing More than anyone else, it was about getting it right for themselves.
Ryan Holiday
I think the Lincoln chapter is, is some of the best writing that I've ever done. I'm proudest of that chapter. It took a lot longer than I thought it would. And I talk about this in the afterword that, you know, I, I, I, I remember as I was laying out the project, I was thinking, okay, I'm gonna have Lincoln there at the end. And I was like, that's the one guy that I'm not gonna have to research, because I've already read, you know, a lot on Lincoln. I've been, I mean, he's one of the main characters in Obstacle. I've just written about him a lot. And then, you know, I sat down to write and I maybe made it, like two paragraphs into that section, and I said, you know what? No, I'm gonna have to do a bunch more. I think I read, you know, three or 4,000 additional pages on Lincoln, which I wasn't expecting to do. But in the whole series, I would say that section on Lincoln, the Queen Elizabeth section in Discipline, and then maybe the, the part two injustice, where I sort of lay out this sort of procession of social justice, I guess, warriors, you might call them. But starting with Thomas Clarkson and the abolitionist movement and leading up into the present moment, just each sort of one of these initiatives that expand the definition of sort of who's an equal citizen under the law. I think those are, those are probably the three that I'm proudest of.
Steve Hanselman
Yeah, I agree. And I, you know, I think having Lincoln at the end of the book in the final section, it really sings.
Ryan Holiday
Because he's the complete man. And that's, I think, what Tolstoy is getting at, that obviously Washington was great and Napoleon was great and Charlemagne was great, all these sort of great heroes and conquerors. Wellington was great. But as human beings, they left a lot to be desired, or the cause itself left a lot to be desired. They're famous primarily for their military genius, their geopolitical sort of statesmanship genius. But it's, it's lacking that. You know, very few people would have said, you know, but they're, but they're just like the best human being that I've ever met.
Steve Hanselman
I think that's right. And you're always very good in balancing the sections with central figures. And of course, in this book, it's sort of Montaigne, Musk, and Lincoln, you know, because, well, as Plutarch taught us long ago, it's through these figures that we can really kind of focus and crystallize the lessons we need.
Ryan Holiday
Do you think people are going to get mad about the Musk section?
Steve Hanselman
Well, you know, Musk has made quite a few people mad all on his own. The last year has been something. Seeing Teslas on fire and crazy, insane stuff like that.
Ryan Holiday
So, yeah, you know, it's funny, I went through that with stillness where I was writing about Mr. Rogers, and then all of a sudden there's a Tom Hanks movie and there's this kind of whole resurgence. And I'm like, no, I thought I was kind of picking someone not from obscurity, but I was picking a unique angle on someone. And then the Musk thing, I mean, I decided to work on that chapter and I believe I began it even before the Twitter purchase. So that one has been weird in that, you know, it's been exhausting in that, like, new things keep having to be added to it, and then I fear it will be read as more political than it was meant to be. Even if I agreed with them on everything, I would have written the exact same chapter.
Steve Hanselman
You took such care with it, and there's such a vast amount of biographical and background information there. I think a lot of people won't even know. So people are going to learn a lot about Musk when they read it.
Ryan Holiday
So, yeah, that was a tough one to write, too. Walter Isaacson is interviewing me at the Texas Tribune Festival in a couple weeks. So we'll have to see if he asked for a copy of the book. So we'll have to see what he thinks of the chapter.
Steve Hanselman
That should be a good discussion.
Ryan Holiday
I interviewed Doris Kearns Goodwin and I ran some of my Lincoln theories by her as the complete man. And I feel like I'm on. On pretty firm ground there.
Steve Hanselman
A very solid source.
Ryan Holiday
All right, so let me ask you something, because I was thinking about this. I took a pretty straight down the middle definition of each of the virtues. You know, maybe I did a little work making temperance a bit more about self discipline than maybe the ancients would have rendered it. I did take a lot of the ancients put the idea of endurance under courage.
Steve Hanselman
Correct.
Ryan Holiday
And that strikes me as incorrect and that it more obviously belongs under the virtue of sophrocyne temperance discipline, what have you. What do you think of that?
Steve Hanselman
Well, I. You know, one of my favorite quotes is from Epictetus, when he's basically saying he can summarize the whole philosophy in two words. Persist and resist. As I like to translate it, it's often translated endure and Renounce? Yes, but he's clearly. We know this from Aulus Gellius, the learned banqueters. That's where the saying is preserved. But he's clearly talking about two virtues there. He's talking about courage, and he's talking about discipline. And so he's got them two right next to each other. And basically Epictetus is saying, this sums.
Ryan Holiday
Up the whole philosophy, although, of course, it doesn't. Right. Because, well, what should you persist and what should you resist? And, yeah, what cause should one's persistence and resistance be directed? This is, I think, why it's more clearly all four of them and interrelated, inseparable way.
Steve Hanselman
For me, when I read that, what I'm getting from it is that the endure and the persist part, that really is about courage. It's about knowing when not to give up and to keep pressing on, when you have every reason. I'm tired, I'm going to get hurt. I won't survive. Courage is what, what keeps you moving forward. And the sort of resist and renounce. That's the discipline of knowing, hey, this isn't good for me. I do not have to go here. I'm going to say, no, I'm going to stick to my knitting, you know.
Ryan Holiday
Yeah. I was thinking about this because I interviewed Kyle Carpenter here the other day, who was a Medal of Honor recipient. He threw himself on a grenade in Afghanistan and saved the life of a comrade. And. And it struck me that courage was that sort of split second decision where the thing came up on the roof and he dove on top of it. That's courage. But then the three years in the hospital where he has to wake up every day as they're literally putting his. His arm and his face and his jaw back together, another skin graft, another rehab session, you know, just the waiting and the patience and the pain, that to me is the endurance. That, to me is persist and resist. That's where the courage crosses the territory into endurance. And there are different forms of courage. But, you know, I was thinking of Seneca's line about how sometimes even to live is an act of courage. Right. But the day to dayness of. Of it, to me is where courage moves over into, you know, this, this idea of temperance or discipline, because it's about. It's about the sustaining and it's about the. The maintaining of that thing, you know, even when you don't want to, like Marcus really says, just that you do the right thing, you know, cold or tired, hungry or well rested. But it's the listing of all that the variables where courage isn't enough. You need this discipline to this will to bring it into the world and make it real.
Steve Hanselman
Right. Yeah. It's going back to Arius Didymus when he's going through all the different virtues and listing the sub virtues that go under it. So when he's talking about courage, he's talking about one of the things he's talking about is philoponia.
Ryan Holiday
Yeah. A love of toil.
Steve Hanselman
Yeah, of toil. Of pain, like. But I think what they're getting at is it's not pain for its own sake. It's like knowing when the fact that something is painful is not enough reason to stop.
Ryan Holiday
Yes.
Steve Hanselman
It's knowing that no, you're going to go over that. The pain is going to pass. And the fact that you didn't give up is what matters.
Ryan Holiday
I do think it's worth pointing out there are virtues and then there are sub virtues. And it's when you get into the business of the sub virtues that I really think you see where they're so intertwined. Like I talked about this in the afterword of the justice book. It's hard to know which virtue love goes into because obviously it goes into all of them. You know, the courage to tell someone you love them. You know, but then I felt like it probably belongs under justice if. If. If anywhere.
Steve Hanselman
Yeah, that's. That's where I would put it. The. The sort of fellowship and, you know, communal feeling. I think that's where they tended to think of it. But obviously, you know, from the standpoint of wisdom, you know, Marcus is always talking about, you know, that wisdom is when we're not just doing it for the sake of our own character, but we're doing it for the sake of the common good.
Ryan Holiday
Yes.
Steve Hanselman
And it's bringing those two things together. For Marcus, he said, the fruits of this life are acts that improve our character and are for the benefit of the common good.
Ryan Holiday
And what is at the core of it, the motivator of most acts of courage or the most transcendent and. And beautiful forms of courage. It's always somebody else or something else that you love more than life itself. Right. That's the famous line from the Bible about, you know, there's no greater love than this than to lay down one's life for their friends. The. The selflessness to go, I'm choosing you over me is the probably the highest and most laudatory form of courage.
Steve Hanselman
Yeah, that's what that whole megalosukya, the greatness of soul was all about this.
Ryan Holiday
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Ryan Holiday
I think I'm glad I waited till the end on Wisdom just because I'm, I'm also six years older. I've read more, I've experienced. I, I knew justice wasn't going to be first and I knew and I knew Wisdom couldn't be first. So that really only left discipline and courage to start off with.
Steve Hanselman
Yeah. Well, I think, you know, in terms of back to your original question of the sort of how it all played out.
Ryan Holiday
Yeah.
Steve Hanselman
You know, the when the justice book came, I mean it was sort of this like complete ruin of public conversation.
Ryan Holiday
Sure.
Steve Hanselman
About the topic. And I remember we went around and around, around if we should even use the word yeah. Or the subtitle. And. And we were all afraid of how it was going to come over, you know, how it was going to go down. And it's the one book that was an instant number one bestseller.
Ryan Holiday
Yeah. I was just going to say I could not have looking at the proposal again, I could not have guessed that of the four books, that's the one that would debut at number one. I guess it remains to be seen on Wisdom. We'll see how it does. But I would have guessed that far and away it would have been the worst.
Steve Hanselman
Yeah. We were all Prepared for that. And, you know, there you go, right out the gate, faster than any of the books.
Ryan Holiday
Yeah, we'll see how this one does. I'm definitely very proud of it. It was an exhausting ordeal. And, yeah, there's some relief at the end, too. Although also, like, a weirdness of, like, every day for six years, I've woken up and I sort of have known what I'm supposed to be working on. Like, I mean, I know what my next project is, but this was a very clear and contained world to live in, and also a very wonderful world to live in because I liked all these people for the most part. I mean, there's some cautionary tales in there for sure, but I mostly wrote about heroes and not villains.
Steve Hanselman
Right. Which, you know, always makes for a good read. It's hard to. The lessons we learn from the villains are they don't travel as well.
Ryan Holiday
The decision to make Musk main character in part two of Wisdom was interesting to me because, you know, at first I was just sort of focused on the sort of decline and the sort of what happened. But then I realized, actually, it's not until you make the positive case first, until you steel man him and you show sort of what a genius he is and how smart he is and how sort of effective this sort of algorithm he developed for thinking about the world and thinking about tough decisions and thinking about innovation. And I think Plutarch does this. Well, I don't think he likes Julius Caesar, but you get both the good and the bad. And, yeah, that was fascinating to me to. When you really first make the case, just the incredible achievement and accomplishment. Because I think the current discourse about Musk, especially sort of in liberal circles, is that he must have been fooling us all along. And I don't think that's right. And so when you look at how you go from here to there, that's really the full arc of it that I think is so compelling and then also cautionary and. Yeah. So no one's ever fully a villain. You've got to show the virtues and the vices, and then you see how the vices eat away at and destroy the one's virtuous thing.
Steve Hanselman
Now, he has many strengths, which obviously produce incredible results for him.
Ryan Holiday
Well, that's the danger, right, is that when someone who has a plausible claim of being one of the smartest people in the world starts to see themselves as one of the smartest people in the world, that's the timeless danger of hubris and the sort of killer of wisdom ultimately is when. When you think you have it, you are in the midst of losing it.
Steve Hanselman
When Marcus said he didn't want to be Caesarified.
Ryan Holiday
Yes.
Steve Hanselman
Stained purple, you know, and it's easy when you're looking at all these, the sort of heroes and the villains, you know, when Epictetus was talking about, you know, education, he would always circle back to this idea that, you know, opinions of what is rational and irrational, what's good, what's evil. It differs, you know, from person to person. Everybody's got their own idea about this stuff, you know, which is precisely why we need education. You know, the process of gaining wisdom is about engaging with our own preconceptions, our own notions of what's rational, of what's good, and working them out in a way that not only conforms with what we're created for, but in keeping with a character that we're trying to development. So it's this. This idea that the heroes and the villains, what we're trying to learn here, it's all about self application and not about sticking our own ruler, you know, on somebody else.
Ryan Holiday
Yes. No, you're supposed to study these lives ultimately, to see yourself reflected in them. That's the whole. That's the whole point. And this goes back even to how the Spartans taught, which is like. It was this constant debate, you know, you're Alexander at this battle. What would you do? You know, you are faced with this ethical dilemma. What would you do? You are here. What would you do? Why would you do it? Why do you think so? And so did X, Y or Z, you know, which is so different than, I think, philosophy today, which is these kind of abstract theoretical questions, mostly removed from any kind of historical context. Right. And, yeah, I think I'm trying to show the stories not to make. To. To raise anyone up or to pull anyone down, but to look at the. The person, for better or for worse, and see what we can take from them. That's why I've always found the criticism strange that, you know, people are like, well, how could you write a book about stoicism? And then in the part one of, you know, the obstacle is the way you're celebrating John D. Rockefeller. He was a robber baron. And it's like, oh, I'm not celebrating John D. Rockefeller. I'm showing you a way in which he was stoic. But we're not talking about social justice in this book. We're talking about overcoming obstacles and being rational. And you could argue that that's his problem. He's hyper rational. All he's thinking about is the objective, you know, value of this or that, how to make more or less. He's not thinking about, you know, the externalities of his discussion of his decisions or the ethics of his decisions or the fairness of the economic system. And so, yeah, what. What you're trying to do is, in each one of these situations is hold this person up for review and take the good and the bad, which is, by the way, what the Stoics do. You know, they're talking about Alexander the Great, and they're talking about Odysseus, and they're talking about, you know, all the emperors that came before and what we can learn from what they did well, and then what we should learn not to do from them.
Steve Hanselman
Yeah. And as we did in lives of the Stoics, you know, there are plenty of situations in which, you know, our Stoic heroes fell down badly. Of course. Yeah. And we have to learn from that, too. You know, Epictetus has this. This sort of metaphor that. About our education that we're basically, we're taking these moral preconceptions that we have, and our education is really about constantly polishing and almost as if they were weapons that we were about to take out into battle.
Ryan Holiday
Yes.
Steve Hanselman
That whole focus of the idea of you're doing this for a reason. You're polishing these because you're going to need them. You're going to need them in your own roles, your own duties, the things that lie ahead for you. He basically says the whole of education is about knowing what is up to us and what's not up to us. And, you know, the question should be, have we learned something? Have we polished, you know, these weapons, and are we engaging the choices and the decisions and the actions which are ours alone to make? If that's what wisdom is, that's a very tough assignment.
Ryan Holiday
I think the idea is, and I say this in the intro of the book, is that at some point in your life, you're going to need to draw on some wisdom. You're going to be making a real tough decision. Right. And not just. We don't just come to this crossroad once. We come to this crossroads constantly. But wisdom is this thing that in moments in your life you desperately need, and you'll have either done that work or not. You'll have either made those deposits and built up that balance, or you haven't. And so that's why I think we have to say wisdom is work. Wisdom is. Is the reaping of seeds that you sowed a Long time ago. Things you read, mentors you had, experiences you underwent, questions you asked. It's this work that you're doing now that you. That you draw on, you know, many years from. From now.
Steve Hanselman
And it's work that we get to do.
Ryan Holiday
I mean, you don't have to.
Steve Hanselman
Epictetus, you know, would always say, you know. You know, people will tell you it's only the free who can be educated.
Ryan Holiday
Yes.
Steve Hanselman
So the sort of wealthy, upper class, the kind of people that he worked for as a slave. Right. You know, they'll tell you, education's only for free people. And Epictetus is, like, wrong.
Ryan Holiday
Yes.
Steve Hanselman
No, only the educated, those who really work at it. They're the only ones who are free. And by that, he meant free to know what is up to them. Sure. What is not up to them. And free to say, you know, what. All that external stuff going on, that doesn't have anything to do with me. I don't have to care about any of it.
Ryan Holiday
Well, I think he's saying also, you know, to know the value of things. Right. He has that famous analogy about banging a coin on the table and knowing whether it's counterfeit or not or what metal's in there or not. If we define wisdom as discernment and judgment, we get a little bit closer to what the Stoics meant by it. They don't mean, oh, that's that old guy who's always able to give you good advice or whatever. Right. No, wisdom was the insight, the ability to sort of know the value and the truth of things more clearly than the people, than your peers and, you know, the moment in time that you happen to live in.
Steve Hanselman
Yeah. And I think it's what, you know. Epictetus was a teacher, one of the, you know, most famous teachers in antiquity, but his teacher, Musonius Rufus.
Ryan Holiday
Yeah.
Steve Hanselman
Was even more famous in his own time. And, you know, he believed that there's this deeper work that's always going on. Whatever our roles and responsibilities in life, there's a deeper work that's going on that takes place at the same time, you know, while we practice the art of living. We're both artisans and artifacts. While we are artisans making things in the world, we're also working on ourselves. And our lives are an artifact that we're leaving behind.
Ryan Holiday
Yes.
Steve Hanselman
And this idea that through our inner work on virtue and character and all the. It's always going on underneath everything else that we do. This is our true education and wisdom and seeing ourselves as both artisans, people who are making Things out there in the world, but also artifacts. And asking ourselves, how have my qualities changed? What am I becoming one?
Ryan Holiday
That ultimately wisdom, like all the other virtues, is something you do, not something you have. It's like they say, there's no such thing as love, there's only loving actions. There really is no such thing as a courageous person or a just person, or a disciplined person or a wise person. There's a person who is doing wisdom. There's a person who is in the.
Steve Hanselman
Middle of a courageous act, turning words into works. And that's.
Ryan Holiday
Yeah, and I think it's worth emphasizing that as we wrap up here like that, that wisdom maybe doesn't feel like that. Like wisdom does feel like the result of the study that you've had or the, the intellectual gifts that you have, or the teachers you have. But no, it's as. It's as much an ongoing thing as any of the other virtues. It's not an end point. And. And if you think you have it, you are exhibiting a sure sign that, that you do not have it. You can acknowledge that you have gotten wiser than you were in the past. But if you think that you are wise, you are missing a critical element of wisdom. Because it's not a place that you arrive at because there's an unlimited amount of it. It's an unlimited, ongoing, endless pursuit that you start, ideally when you're young, but you could start it right now. And the point is that you don't ever finish it.
Steve Hanselman
Yeah, it's a constant work progress, not perfection.
Ryan Holiday
Because I used this thing at the beginning. It's like the horizon. You feel like you're walking towards it, but it's not getting any closer. But one of the things, if you. Tonight you started heading towards the sunset, after a certain point, you'd look back and you'd notice that you actually have traveled quite a far distance. You've not made it any closer to the destination, but you have traveled afar. Right. Because the destination is pulling ahead of you each time. But that doesn't negate the significant progress you've made or distance that you've traveled. And so that's kind of the paradoxical nature of wisdom.
Steve Hanselman
Absolutely. And this whole sense of well being or flourishing that comes with the virtues. It's not like we're without a clue when we're in the groove or not in the groove, you know? Yes, we know when life is flowing better and we know when it's not. And as Zeno said, wellbeing's realized step by step.
Ryan Holiday
But it's no small thing, right? He says it's realized by small steps, but it's no small thing. That's one of my absolute favorites. Well, Steve, thank you for helping me make this a reality. I love that. I could call you after that hike and 2019. And then here we are six years later, and I've got all. Got all four of them. I love it.
Steve Hanselman
Congratulations.
Ryan Holiday
Yeah, thank you.
Steve Hanselman
There it is.
Ryan Holiday
I'm very excited. I got 17 hours of. Of transcripts of an oral history for the book that I'm working on now. We just. We just discovered it. No one thought it existed, but we just found 17 hours of interviews with the. With the main subject. So I'm. I'm raring to get back to my office to dig into that.
Steve Hanselman
Tremendously exciting.
Ryan Holiday
Yeah. Amazing. Steve, thanks for everything.
Steve Hanselman
All right, Ryan.
Ryan 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 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. Look, ads are annoying. They are to be avoided if at all possible. I understand a content creator, why they need to exist. That's why I don't begrudge them when they appear on the shows that I listen to. But again, as a person who has to pay a podcast producer and has to pay for equipment and for the studio and the building that the studio is in, it's a lot to keep something like the Daily Stoic going. So if you want to support a show but not listen to ads, well, we have partnered with Supercast to bring you a ad free version of Daily Stoic. We're calling it Daily Stoic Premium. And with Premium, you can listen to every episode of the Daily Stoic podcast completely ad free. No interruptions, just the ideas, just the messages, just the conversations you came here for. And you can also get early access to episodes before they're available to the public. And we're going to have a bunch of exclusive bonus content and extended interviews in there just for Daily Stoic Premium members as well. If you want to remove distractions, go deeper into Stoicism and support the work we do here. Well, it takes less than a minute to sign up for Daily Stoic Premium, and we are offering a limited time discount of 20% off your first year. Just go to Dailystoic.com premium to sign up right now or click the link in the show descriptions to make those ads go away.
Episode Title: BONUS: The Man Behind The Daily Stoic (Not Ryan Holiday)
Airdate: October 26, 2025
Host: Ryan Holiday
Guest: Steve Hanselman (Book agent, co-writer, collaborator)
This special bonus episode features a rare, in-depth conversation between Ryan Holiday and Steve Hanselman—Holiday’s longtime literary agent, collaborator, and the pivotal figure behind the creation of the Daily Stoic project. The episode delves into their multi-year journey creating the Daily Stoic books, with a particular focus on the upcoming release, Wisdom Takes Work (the fourth and final installment in Holiday’s virtues series). The discussion covers the origin story of the "Daily Stoic," the philosophical challenges of writing about the four cardinal virtues, the interwoven nature of those virtues, and reflections on figures like Marcus Aurelius, Lincoln, and Elon Musk.
[04:10-08:31]
Ryan recounts that despite his own pivotal role, the Daily Stoic wouldn’t exist without Steve Hanselman:
“There’s basically one person to thank for this all existing. Not me. ... It all traces back to a conversation I had with Steve Hanselman, my agent.”
(Ryan Holiday, 04:16)
Steve proposed the "page-a-day" format, inspired by "The Daily Drucker" from Peter Drucker’s writings. Ryan was initially skeptical but realized its potential as an accessible entry point:
“These are a way to live with the thinking of someone, not just for a year, but over and over and over again.”
(Ryan Holiday, paraphrasing Hanselman, 05:22)
Notably, Steve volunteered to produce original Stoic translations based on his background in Greek and Latin.
“I’ll do the translations... I went to Harvard Divinity School. I know both Latin and Greek.”
(Steve Hanselman, paraphrased by Ryan Holiday, 06:11)
[08:31-14:47]
The book series was conceived on a family hike and grew organically into a major project over six years.
“I remember you were out on a family hike first, called me with the idea for the series and we both got so excited about it.”
(Steve Hanselman, 08:32)
The four cardinal virtues (Courage, Temperance/Discipline, Justice, Wisdom) became the structure, echoing ancient Stoic debates.
Steve and Ryan discuss how Christianity was influenced by Stoic virtues, with Paul himself borrowing heavily from philosophy:
“Paul was a student of the philosophers…even quoting the Stoics, you know, to the audience.”
(Steve Hanselman, 10:02)
Key insight: These virtues are not just religious, but have a philosophical—and practical—origin.
[15:18-20:06, 24:31-27:53]
The challenge of separating the virtues:
“Where does one begin and the other end? That’s really the tricky part of the whole thing.”
(Ryan Holiday, 15:32)
Courage almost always overlaps with justice and wisdom, both at a moral and practical level.
Steve highlights how the Stoics shifted toward a "social courage" (megalosukiya or ‘greatness of soul’), particularly in Roman times.
Ryan emphasizes that wisdom is not just theoretical, but practical (phronesis):
"They used the word phronesis, which was practical wisdom. ... It was something we had to engage in, everything that we do."
(Steve Hanselman, 24:33)
[27:21-32:19]
Wisdom is inherently about application and openness to correction:
“Wisdom is the ability to go through life ready to change your mind. Doesn’t mean we abandon our values because they’re inconvenient. But our thinking is supposed to evolve, we’re supposed to grow.”
(Ryan Holiday, 28:14, quoting his own book)
Marcus Aurelius is held up as a paragon of being open to correction despite his absolute power:
“He talks about being wrong and changing his mind ... His word can literally mean life or death.”
(Ryan Holiday, 28:39)
The paradox of creative success: as your authority grows, you receive less outside correction, which can be risky for writers and thinkers:
“When the stakes are highest, you’re actually getting the least amount of feedback and editing and accountability, right?”
(Ryan Holiday, 30:44)
[34:05-41:06]
Ryan and Steve discuss how both Stoic and modern figures embody and transmit these virtues.
Lincoln and Cleanthes are presented as models of learning and humility.
“They never forgot what they learned. ... It was about getting it right for themselves.”
(Steve Hanselman, 36:22)
On wisdom as internalized, hard-won, and self-motivated—not for external validation.
The inclusion of Elon Musk as a controversial but instructive case:
“Do you think people are going to get mad about the Musk section?”
(Ryan Holiday, 39:54)
“Musk has made quite a few people mad all on his own.”
(Steve Hanselman, 39:58)
Ryan explains his method: show both strengths and weaknesses, as Plutarch did. Musk epitomizes the danger of brilliance devolving into hubris.
[41:33-48:03]
[54:47-63:08]
Studying great lives is not about hero worship but seeing ourselves reflected and learning from their strengths and failings:
"You're supposed to study these lives ultimately, to see yourself reflected in them. That's the whole point."
(Ryan Holiday, 54:47)
The Stoic model: “constant debate”—if you’re Alexander at this battle, what would you do? Stoicism embraces practical application over abstract theorizing.
Wisdom is a lifelong process, not a destination:
“If you think you have it, you are exhibiting a sure sign that you do not have it.”
(Ryan Holiday, 62:08)
“It’s not an endpoint. ... And the point is that you don’t ever finish it.”
(Ryan Holiday, 63:08)
[63:49-64:31]
“Congratulations.”
(Steve Hanselman, 64:31)
This episode offers an unusually candid and philosophical look behind the scenes at how the Daily Stoic books came to be, and how their creation became a dialogue across centuries—between agents, modern writers, and ancient teachers. Core themes include the interdependence of the virtues, wisdom as a dynamic process, and the ongoing challenge of self-improvement. Both Ryan and Steve model what it looks like to be “in the work”—constantly questioning, refining, and learning. As they close out the virtues project, listeners are reminded that stoicism isn’t about knowing everything, but about never ceasing to seek and apply wisdom in daily life.