Turn The Tables | Billy Oppenheimer Asks Ryan Holiday About His Writing Evolution and Creative Fulfillment

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1:04Welcome to the weekend edition of The Daily Stoic. Each weekday, we bring you a meditation inspired by the ancient Stoics, something to help you live up to those four Stoic virtues of courage, justice, temperance, and wisdom. And then here on the weekend, we take a deeper dive into those same topics. We interview Stoic philosophers, we explore at length how these stoic ideas can be applied to our actual lives and the challenging issues of our time. Here on the weekend, when you have a little bit more space, when things have slowed down, be sure to take some time to think, to go for a walk, to sit with your journal, and most importantly, to prepare for what the week ahead may bring.

1:55Hey, it's Ryan Holiday. Welcome to another episode of the Daily Stoic Podcast. Last Sunday, I went to Josephine House in Austin with my wife who went on a date. And I was like, when was I here last? Why was I here last? And then I realized I had upstairs interviewed Tim Ferris. He asked me to come out and interview him for the Tim Ferris Show. And I was like, oh yeah, that's what I did here. And then I remember we came downstairs and had lunch afterwards. And I realized I hadn't been there since. It must have been four years ago, five years ago. Anyways, I always liked that experience. And I think he liked it.

2:35It was a chance for him to talk about stuff that, you know, when you have a podcast, it's supposed to be about the guests, right? So you're always asking them questions. I probably talk too much on this show. But I know you guys had some questions. There were some things I wanted to talk about. So I had Billy Oppenheimer who started as my research assistant many years ago. But back in January, we sat down and talked. I think it was a great conversation. And he's going to be the one interviewing me today. And I'm excited to bring that to you. You can follow his awesome newsletter, which I get every week.

3:11His six at six newsletter, which you can grab over at Billy Oppenheimer.com. He has a book coming out next year, I think. So anyways, it's one of the few newsletters I get every week that I really like. And there's a bunch to talk about here. And I think you're really going to like this.

3:32I thought we'd start with the story of you writing about stoicism in 2009. Yeah. And it leading to a book offer that you didn't take. Yeah. So I remember, I mean, I was writing about stoicism much earlier than that because I read Mark Strelius in 2006. And I just, I did what I think stoicism is supposed to be, which is this sort of public slash private conversation about what the ideas mean and how they connect to your life and other people's lives. So I was writing about it on my little website at the time. And And then I met Tim Ferriss a couple of years after that, and his blog had sort of blown up.

4:15And he and I shared this interest in stoicism. And he said, hey, would you want to write an article about stoicism for my site? And I said, yes. And it's probably the first time I ever wrote for something other than myself where there was already an audience. And so that was very intimidating and strange. And I don't remember the piece exactly, but I remember obviously sort of really stressing out about it, ironically, and then sort of putting it together. It came out and it did, I think it did really well. But I remember maybe a year later, I was the director of marketing at American Apparel.

4:49And there was an address, I don't know what they're called, but like a distro email that like a bunch of us who worked in marketing or PR, whatever, in the company, like the people who managed like press inquiries, it went to all of us if you emailed like press at AmericanApparel.net or something. and somebody at a company called Greenleaf, which is a small sort of indie publisher, it's a hybrid publisher, they emailed that address and said, hey, I read this article, I wanna, I think you should do a book about it. And I was like both excited and mortified at the same time. I was mortified because I was kind of doing this stuff on the side.

5:30I mean, I had permission from the owner of the company to sort of do other stuff. That was part of my employment that I wasn't gonna stop writing. But it was like my professional world. And then the thing I really wanted to do kind of intersected in a way that was like mortifying. And I was self-conscious about because I didn't I prefer to like keep the separation of church and state. So anyways, I ended up talking to the guy and he was he offered me a deal, which was, you know, not really a deal in the sense of like there's basically no advance. I think you may even have to pay for part of the first run.

6:02It was just not a good deal. but it was still a book deal. Like a publishing house that had published books, some of which had sold a lot of copies, wanted me to do a book about the thing I wanted to write a book about. And I remember I called Robert Greene and I was somewhere in downtown LA because I remember sort of pacing while I did the call and Robert, I sort of laid it all out. And I thought Robert was gonna be like, of course you should do it. This is what you've been, you know? And he was like, no, you shouldn't do it. And I was like, what do you mean? And he said a couple of things. I think he said, one, it's not a good deal because he obviously knew publishing, which is why it's important to have people who are further ahead than you.

6:40So you don't make, when you hear about people making stupid business decisions, it's because they didn't know. Like, and the industries are designed to take advantage of your naivete. They want the people sort of fresh off the truck to make stupid decisions. and I'm sure when you got offered yours, if you didn't know any better, you're like literally$1 is more than I was getting paid before. So yes, you need someone to be able to tell you what market is and what's standard and what's not standard. And so Robert was able to point out a bunch of things that made this not actually that attractive.

7:17But then he said, look, I think you're too young to do the book. And he's like, I don't mean that like you couldn't do the book. Of course you could do it. And if you did do it, it would be successful. He says, I think you're getting better every day and you're experiencing more every day. This is a book that will be better later or you will do better later. And so I took the advice and thankfully I was busy. I had other stuff. It's not like I had to go back to like sleeping on the floor somewhere. But I, so trust me, I'm lying in 2011. So that's two-ish year, two plus years later, came out a year after that.

7:53So that's three. and then, you know, probably set me back four or five years, but I don't think, I wouldn't have called it the, like, even what became the title, The Obstacle is the Way, that was, I discovered that much later. So it couldn't have possibly been the same book. So you need people, part of stoicism is like, don't get too excited about things, step back, see big picture, be rational. And that's what Robert was helping me do. And that's what mentors and sort of people further along than you can help you do. So something I needed to do, you need someone to be like, I don't care what your dream is.

8:32Here's the smart way to do it. Right. How long had you been working for Robert by that point? I'd probably known Robert since maybe 2006, so three years. What did you learn from working, not just from things he said to you, but observing him go about his work? Well, Robert's very sort of monkish, you know, like I worked for Robert for many years. And I would say for the first several years, I probably spent like cumulatively, like a couple hours with him. He was all business. He had very clear boundaries. He's not just like inviting people into his life. You know, he'd be like, I need you to research this, like drop it off on my back porch or drop it off on my front porch.

9:18I need you to transcribe this and then email me that. And then, I mean, he was always very open if I ever had questions or if I ever had thoughts, but like, you know, he wasn't a friendship. I think people think like mentors are your best friends. They invite you into their life. Actually, I find the best mentors have really strong boundaries. They're protected. They've done this before, right? They've seen you before. And so they don't get too attached at first. They, uh, they let you sort of develop and prove yourself. And if you, you show whether you are worthy of more or less investment. Right.

9:54And so that was a, you know, that was a, an experience and, you know, at no point was he ever like, I am your mentor. Right. You know, I think there's a good reason. There's not even a good word for what being someone's mentor is. Like I never hear any serious people say mentee, you know, but the idea of it being an apprenticeship, that was something that developed over time. It's a word that came up later. And for the first good chunk of time, it was, although he would explicitly give me instruction and guidance on things he wanted me to do, of the vast majority of what I took was what I was observing about Robert asked me to do this thing.

10:33He sent me off to research this thing and he paid me many hours to do it. And then it just doesn't quite, it's not quite to the level of what he wants. It doesn't quite. And he's like, no, I'll do it. So I think one of the big things I took was just how selective he was and how high his standards were, not for me. I mean, he had high standards for me, but high standards of what he included in his books or not. He wasn't like something being in the ballpark of illustrating the point he wanted is not what it takes. It has to be exactly. Yeah. Or like, just because Ryan invested a bunch of time in this, I should feel like I have to use it.

11:13And I feel like a lot of what he had me do, especially early on, was like, there might be something here, go explore it. And what I was actually doing was eliminating. It was like, there was a 5 % chance that the life story of some, I don't know, medieval astronomer might have something, but the upside was too low for him to read an 800-page book about it, but I could read it. And then if I was like, I think there's something here, then maybe he would... So I was really... I was doing cleanup early on, especially, which is also the idea that you're also just making sure you're not leaving stones unturned as opposed to, I know there's something here and I want you to find what's there.

12:04Yeah. How did you think about deliberately deviating from his style? Because you're obviously very influenced by it, but you don't want to just be like, this is obviously a Robert Greene knockoff piece. Because you're very distinct, but also clearly influenced. It's a timeless question of like you're influenced by someone, you aspire to be like someone, but then you don't want to copy that person and you don't want to be like a shitty knockoff of that person. There's actually a really great book by, I think it's Harold Bloom, called The Anxiety of Influence. And his point is that he's specifically talking, I think, of Shakespeare, that basically every person is influenced by the generation or the great that came before you.

12:50and you sort of are imitating what they're doing, but then there has to be this swerve where you separate yourself from them and you come up with something different that you do. Otherwise you are really just a facsimile. And that basically though, no one has ever surpassed the person that came before them other than Shakespeare eclipsed pretty much everyone that came before him, but then everyone on down is just swerving from the swerve of the person who was swerving from Shakespeare. So there's a kind of humility in that, that you'll never surpass the mentor or the teacher, really. All you can do is try to do it slightly differently in your own way.

13:28So I think what Robert does is so distinctive is the sort of marginalia in the books and the colors and the design elements. I thought that was really cool. So it was like, that's so cool and distinctive. It's off the table. Obviously, Robert's distinctive in the 48 Laws of Power, some of the other books is like observance of the law, transgression of the law. I decided, yeah, like that's, you can't do that. So I think this first time it's like, what did that, what does that person do? That's totally their own. And, and then you, you have to respect that and you have to go, I'm, I have to go in a different direction.

14:01I have to make my own way. So what Robert didn't invent is the idea of illustrating through story and, and through sort of parables that prove a larger idea. And as I went and I read a bunch of other books, I found how many other people did that thing. This is, of course, what Plutarch does. I read this book called How They Succeeded by this guy, I think his name's Orison Sweat Martin. He was kind of a self-help writer in the early 1900s. Samuel Smiles, the inventor of self-help around the US Civil War in the 1860s, he kind of did it so much. So I noticed, like, oh, this is a genre of things. So I felt comfortable doing that.

14:41And then I just decided, yeah, I'm going to strip it way down. And sometimes like in the obstacles way, sometimes I'm showing people observing and sometimes I'm showing transgressions. You can't just do stories of people holding up the idea. You do have to show people failing to live up to the idea, but I would just sort of integrate it in my own way. And I remember I was in a Starbucks in Riverside, California, kind of really working on the book. And I just couldn't figure out the style and the tone. And you just kind of fuck with stuff the way that a musician is like trying to solve this problem.

15:19And then it kind of just comes to you. And I remember just some version of the Rockefeller Discipline and Perception chapter came there and I jotted, I got the core of it down in probably a single sitting. And then I showed it to someone and they're like, that's great, that works. And I built the book around that thing that was working. And then what do you think you specifically like writing lessons embedded in like stoicism and what you learned and applied to your writing from like reading and then studying the stoics? So the other thing though, from Robert, I also was like, my books are gonna be much shorter.

15:53They're gonna be much shorter and they're going to be around like a very specific idea as opposed to this large, like bigger, bigger, like, uh, there were going to be small ideas and I was going to do more of them. So I think that, that was another one for me. But, um, so what, so what I learned from writing about stoicism? No, from like studying the stoics, like, what did you pick up about? like oh well you know you read mark's really his meditations what's so incredible about it is like you have this guy you have this guy and he's writing to himself in greek right not really thinking of an audience and it's just so it's so just to the point i i once i was once a fortunate man but at some point fortune abandoned me but true good fortune is what you make for yourself good fortune and then he just good fortune colon good character good intentions and good actions so you know he's talking to himself not to the audience but he's not talking about himself and then he's kind of writing this is the hayes translation which i i think does it the most readably but then there's kind of this like straightforward like almost shorthand to it like if that's not a complete sentence like good character colon and then listing a bunch of things that are parts of good character.

17:14You know, that's, that's, if you were just trying to get it down, it's, there's something Hemingway-esque about it and, and straightforward about it, but also still lyrical and poetic about it. And so I think that style definitely influenced me, but then also this is when blogging as a writing style is coming and there's, there was a colloquialness to it and a personalness to it, but also a kind of a, freedom in terms of how you want to do your style. And so I think that was all forming me at the same time. So I see him as a mate. Marcus Reyes is not just a philosophical influence on me. He's a stylistic influence on me.

17:54Seneca too. I mean, these letters are short and to the point, like a blog post, right? And he's personal, but also universal at the same time. So I think I was very influenced by the Stoics as writers. And I think there's a reason that Marcus Aurelius, Epictetus, Seneca are like the philosophy texts that self-taught people are the most drawn to, because they're for regular people. There's this line, Epictetus is over here, some of his students bragging about having read Chrysippus, who was one of the harder to read Stoics. Almost nothing of his survives. But from what we know, he wrote a lot and it was closer to what we would think of as a philosopher's writing today.

18:38He's bragging about having made his way through all the works. And Epictetus says, you know, if Chrysippus was a better writer, you'd have less to be proud of. And I think that's what's so great about the Stokes is that they were great writers. And as a result, they are not celebrated as great philosophers by academics or even as great writers. The mark of being a master of something is you make it look easy or that you don't even understand. The audience doesn't understand how hard or what is happening. And so I think Marcus doesn't get his due as a stylist and as a writer, but I think the Stoics influenced me creatively and stylistically as they did philosophically.

19:21I don't know if it still says this, but on your site, it used to say meditations on strategy in life. yeah is that a nod to his meditations yeah i mean i don't remember why i picked that or when i picked that but i had to come up with something and obviously professionally i was a media strategist and a publicist and so and i obviously having worked for robert i was thinking about sort of those things a lot and then just a kid trying to figure out the world that's what i was thinking So yeah, it was sort of meditations. And I would sometimes write little kind of Marcus Aurelius-inspired meditations because the format of what became the Daily Stoic, I mean, I had been writing for 10 years when the Daily Stoic came out.

20:07So that format of like this sort of little entry in story thing, that came much later. And that was sort of development of, I would write all sorts of stuff and I would write websites. I wrote articles. I had a media column. Like I wrote like anywhere and everywhere they would have me because I was just trying to get my reps, which is what you have to do. You get your reps. And I mean, I've probably written 100, 150 press releases in my life. I've written reports. I've written essays. God knows how many emails I've done. I've written articles. I've written answers to questions for reporters on behalf of us.

20:44So I just, I wrote hundreds of thousands of words in every format you can imagine. Some of it under my own name, some of it not under my own name, some of it like sort of corporate drivel and some of it memos and some of it, you know, public facing, some of it product copy. I just wanted to get reps at the thing. And then once you have lots and lots of reps, you can narrow that down into what you want to do. And you have to earn the platform or the financial freedom to be able to do only what you want to do. Yeah.

21:37Thanks to Toyota Trucks for sponsoring this episode. When I bought my ranch in 2015 out here in Bastro 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.

22:22We got to go deep into the hill country's wild beauty. We've driven all the way out to East Texas. We've driven 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.

23:01Discover your uncharted territory. Learn more at toyota.com slash trucks slash adventure dash detours. We just took our kids to an outdoor performance at the Nutcracker. They had a snow cone and then they went insane in the car ride home. And one of the things I try to remind myself when that's happening is that I don't control my kids' behavior, especially when they're too far gone like that, but I do control how I respond, right? That's stoicism, but it's also what Dr. Becky talks about. Dr. Becky is a clinical psychologist and a best-selling author, and she founded Good Inside, which is there to give parents practical, actionable tools for handling those everyday challenges with confidence.

23:45My wife introduced me to Dr. Becky's books. I love them. I've recommended them a million times. I've had her on the podcast. And as it happens, Dr. Becky is hosting two live Q &A events for good inside members. I am one of them. She signed me up for it about a year and a half ago. I've loved it ever since. On December 1st, you can join Dr. Becky for her How Not to Raise Assholes event, which is about avoiding entitlement and raising kind, empathetic kids. And on December 15th, she's hosting her How Not to Lose It Over the Holidays event, which I'm sure we could all use. As I said, I'm a big fan of Dr.

24:22Becky. She's been a great influence for me as a parent and just as a human being. And Daily Stoic listeners can join for 15 % off with code STOIC15. You just got to head over to goodinside.com to catch the events.

24:42when you look back at some of the early writing what about it sort of makes you cringe now or is like what did you learn through that that's like this is a common mistake i was writing as an early writer the cringe the things that make you cringe when you look back on your life and And then also as like creative, I think the thing that strikes me the most is certainty. That's the thing that ages the least well. So when I was saying something very emphatic, very black and white, very short about a very complex nuanced thing that maybe I only had partly experienced, that's the stuff that doesn't age well.

25:24That's why I look back on almost zero tweets that I wrote, especially anything in the box of Flitter, where I was like, I have to say this. There's nothing I'm like, I'm so glad I said that. Because you're responding with something ephemeral in real time, and you're doing it in a very small space. I mean, it used to be only 140 characters. Chances are on the fly, something about 140, that's only 140 characters. That is not going to be, that's not going to age well. It's not going to hold up well. And you're probably going to cringe and regret it. And so like, I've had to go back and I did a couple editions of Trust Me, I'm Lying.

26:08I'm just now doing a 10 year anniversary of The Obstacles Away. What I like about those books is I like discipline and obstacle. I mean, it's like maybe twice as long. um i like how punchy and short obstacle is but part of that i would never let myself get away with that now and when i read when i added to what's going to be the new edition i mean there are some like additional examples i did but there's also just things that i felt like have to be qualified now or rounded out more or needed more empathy um or just you know like i said like so that that story of rockefeller comes to me as i'm writing you know the first draft of the obstacles away.

26:48And I'm just talking about what I admired in Rockefeller and what was great in Rockefeller. Because I'd only really read one thing about him. And I'd only seen however many years of life that I'd seen at that point. And now that I've experienced more history, now that I've met people like him, now that I've read more about him and that era, I wouldn't do it the same way. And so getting this chance to do it a little bit differently, I'm going to talk about a fuller picture, right? And so that tension between, you know, sort of youthful energy and drive and, you know, you just don't know what you don't know.

27:25And so you tend to get longer as you go. Of course, I'll cringe about stuff I'm doing now in the future, but I hope there's less cringe because I do try to address that tendency to be flip or unempathetic or black and white or whatever. Back to the sort of style of using story to illustrate concepts. What do you think are like the keys to good storytelling? Well, when I was thinking about doing The Office of His Way, I think that was one of the things Robert was telling me about not to do. He's like, you just haven't done enough research yet. Yeah. He's like, you've only read so many books. You've only experienced so many things.

28:05He's like, you'll have more stories in the future, which is of course true. If I was doing now eight or nine years after the Daily Stoic, there's different stories I would plug in that I just didn't know. There's different things I know about the Stoics that I didn't know. But I don't know, when I'm thinking about a story, so Plutarch is maybe the greatest biographer that ever lived. He said that when you're studying great men and women of history, there's often like a shrug of the shoulders or an exchange of words or a single moment that captures the essence of their life, what to do or not do, their fatal flaw or their fundamental decency that's captured in these small little moments more than exactly what they did at this enormous battle or you know, how they achieved this success or that success.

29:07And so I think one of the things when you're telling stories, you're often looking for little things that demonstrate the larger essence of that person. So in the Obstacles Way, I talk a lot about Ulysses S. Grant. You know, there's little stories. He's in Matthew Brady's studio and someone breaks a skylight and the glass comes shattering down and he doesn't move. He's just like, all right, you know. Now, there's a new one I just added in, I think it's from the Chernow biography, where Grant's father wanted to prove how controlled his son was and how difficult he was to scare. And he fired a gun next to his son to show a neighbor that his son wouldn't jump.

29:47And Ulysses S. Grant didn't jump and then said to his dad, he said, he said, fic it again, fic it again, fic it again. I mean, like, you know, the hammer, do it again. And, you know, so like I already am making the larger point. People understand that what made Grant great was his doggedness, his determination. You know, he wasn't scared. He wasn't easily intimidated. He persevered. But then you're looking for little examples that demonstrate that. And then hopefully those are examples that stick with people. And Robert's the master of this. I remember I was at a dinner party many, many years ago, right?

30:23As I was thinking about starting to be a writer. and someone heard that I was working for Robert Greene and then someone else was like, who's this Robert Greene guy? Robert Greene wrote this book, 48 Laws of Power and just filled these amazing stories. And the man proceeded to tell one of the best stories in the 48 Laws of Power, which is this architect is building for some Pope or Bishop or something. And the guy's always meddling and you got to do this, you got to do this. And the guy just knew what he was doing and he didn't like being interfered with. And the patron was insisting that the whole thing was going to collapse without this column that needed to be in the middle or something.

30:56And the guy aesthetically hated the column and he knew the column didn't need to be there. It interfered with his design or it didn't add any extra support. So he builds it and he builds it all the way up, but he leaves like a one inch gap between the top of the column. So later when the building was, you know, renovated or excavated or whatever, it was this sort of subtle fuck you and demonstration that his design did not need the thing. And, you know, just watching this guy repeat a story that Robert had told in the 48 Lines of Power. And that story is probably in Vasari's The Lives of Eminent Artists and Painters, which is also an incredible book that I want you to read.

31:37Watching how Robert had told a story to demonstrate a point that he had found in a book that I had also read. I was like, oh, that's the magic of it. Like you take the story, you retell it and you connect it to a more modern context and you're giving something people, you're giving something to people that they can talk about at dinner, not just to share a lesson, but also to rave about what you did. And that, that kind of connected a bunch of dots for me. Yeah. You once told me in some of my early writing I was doing, I would like spin my wheels into the story and you called me once and you said, you know, that story I tell, I think it's encouraged to go for the third story.

32:20Yeah. And you're like, that's what you need to start doing. Grab the reader by the collar and pull them into the story. Yeah. And I think about that all the time. And I was like, how does the first sentence immediately grab the reader? Well, I think in The Sun Also Rises, there was like an intro and a preface and another chapter that kind of explained all the characters and who they were and what their motivations were. and Fitzgerald, who was like a mentor to Hemingway, even though Hemingway was awful to him, read a draft of it and he was like, cut all this, like start here. And it starts wherever, I forget what the first lines in The Sun All Rises are, but he cuts it there.

33:01And Fitzgerald's point was like, basically this is all wheel spinning and like the motivations and the essence of the characters will be because you wrote a great book, but should be, if you do it right, evident in what actually happens and what they do. And as a writer, you can often, you just feel, there's just a lot of prologue in what you're doing. Not you, but all writers. You're just like, you're setting it up. You're setting it up. You're setting it up. Really, you just got to fucking say it. And people don't have time for prologue. They don't have interest in prologue. You just got to, you got to distill it down to the essence of what you're saying.

33:40And you got to cut the extraneous stuff. So yeah, I think early on, a lot of that wheel spinning is insecurity. Because you don't feel like you have the authorial voice to be like, this is what I am saying. Or this is what you need to know. You feel like you need to warm up to it instead of just saying it. The reader or the audience can feel that insecurity. And it's true in clips or Instagram stuff or social media stuff now. You know the millennial pause? so like millennials like me who didn't grow up with camera phones we hit record because like when we were kids like you would have a camera like these you go and it go beep and then it would take a second to start right and so like we like do that and we wait for a second and then we start whereas apparently the stereotype is that gen z just was like start just like starts talking before the recording even starts you're just like in it and so that's what the audience expects but that's true in all mediums is like, you don't, you don't have the luxury of the pause.

34:44You don't have the luxury of the throat clearing. You don't have the luxury of the, I'm just getting comfortable first. You have to go for the throat. You have to like, start with what you're going to say in journalism. They used to call this the inverted pyramid, but you got to start with the good shit. And then if you hook them with a good shit, you can give them more and you can do the nuance qualifications later. I remember like for, for daily stock, we used to start the reels and I would go, there's this great quote from Marcus Aurelius that says this. So that's like three, four seconds. And so if you're interested in Marcus Aurelius and you know who I am, then sure, maybe you'll be like, oh, this is what Ryan does, whatever.

35:22But actually the ones that perform best is if I go, you could leave life right now, Marcus Aurelius said. You start with the core of the quote. And then you can go back and be like, by the way, that's who was saying that, right? It's not that life is short. It's that we waste a lot of it. That was Seneca's line, as opposed to Seneca's line in on the shortness of life, which he wrote in Rome in insert year. You know what I mean? You're just wasting people's time. You can give that after they have bought in. How has making video content, podcasting, how has that influence gone back to the way you write?

36:04For instance, because Twitter, you really have to get straight to the point and hook people in to get them to read a fuller post. Doing that, I now carry that over to the newsletter writing I do. interesting do you think it has like for me like do you think the social media stuff for the video stuff do you think it shaped the writing like can you tell no oh interesting i don't know if it has i could make up that it has but i don't know if it has do you know what i mean like i like i would compartmentalize them and like this is how i approach video content this is how i approach writing well i really like the writing is the one that's important to me and it's what i work the hardest on and what I have the highest standards for.

36:48So I don't know how much it shaped. I mean, I already had a bunch of strong influences in that regard. Like, so Tim Ferriss told me once that every chapter in a book should be able to be ripped out of the book and published independently, like as an article and that title of it should work as an art. Like, so I already was kind of thinking about that. So I wasn't allowing myself a huge sort of ponderous, you know, whatever, or a long runway. I was always kind of like tight or whatever. I think more I've been shaped by doing the social media stuff in that it's given me a sense of what stuff people respond to.

37:26Like the quotes that really resonate with me are not always the quotes or the ideas that really resonate with other people. So you get, you just get a sense of like where you are versus the audience is. That's interesting. And then I think it's just been more like writing, being good at writing and writing a lot is an important communication tool and style, but it's not necessarily super transferable to the other mediums. So I think what the social media stuff has done and podcasts have done, speaking has done, which are all very different, but they've forced me to do a thing, which I don't think a lot of writers are as good at, which is that I can communicate the ideas in multiple mediums per whatever that medium demands.

38:11So it's just made me more of a Swiss army knife than like a specialist. Yeah.

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39:58On that idea of like that overlap between stuff you find interesting and an audience. How do you think about the tension between like doing a thing because this is what I like to do? Yeah. But then also being cognizant of like, but I also wanted to land with an audience, but then not letting that sort of like... Well, the way I think about it is I have things that I want to say that are important to me that I think matter. And the primary medium, which I get the most pleasure and meaning in participating in is writing. So that's like assumption number one is like I communicate via writing because I love books.

40:35But then it's realizing that all my books cumulatively have sold slash reached what we might reach via social media in a week. So to be like, right, to be pretentious or snobby or to ignore these other mediums is to, one, say that you don't actually care that much about what you're saying. And two, it's also to seed that field to other people who might not be saying it as well or might be abusing it or manipulating it. Do you know what I mean? Like, so when people criticize, when academics criticize Malcolm Gladwell as a popularizer, perhaps he is, right? And perhaps he's not representing it the way that it should be represented.

41:18I don't think that's true. I think he's great. But they are not guiltless in the market existing where he needs to do that. In fact, they are primarily responsible for it. They chose to communicate their ideas in arcane or pedantic or inaccessible mediums. They chose to communicate primarily with other academics and they ignored the fact that their teachings and their insights and their research could be interesting and could have impact in regular, normal people's lives. And they failed to do it. Do you know what I mean? Like he is serving a need that they chose not to serve. And in fact, I said not even serving a need, he is providing a valuable service by popularizing important ideas.

42:05I, who also get called a popularizer, it doesn't hurt my feelings at all. You could call me a lot worse things than popularizer of a school of ancient philosophy. It's like, show me other people that have done that. You know what I mean? It's hard to do, but there's a, I guess there's a tension. I just meant like not allow, like not just sitting down with like, like pandering or getting captured by the audience. No audience capture is the primary sort of creative problem of our time. People go, I know my audience. Then they make shit for that audience. But the audience is drifting and you are drifting and it can be often a wicked feedback loop.

42:41And you watch people become more and more extreme, especially when people are like, oh, Substack's better because there's no censorship. It's better incentives. Actually, no, now you're at the mercy of the audience because they'll unsubscribe if they don't like what you're talking about. So you watch someone who says they get canceled or they do something politically controversial. It's very quick that that becomes 100 % of who they are and what they do. It's just they're hitting that same note over and over again. But because the audience only wants to hear that note so many times, it has to escalate.

43:17You know what I mean? I think you see this with vaccine skeptics or people are flirting with extreme right-wing ideas, maybe even some extreme left-wing ideas, but it tends to be not as pronounced there. But yeah, you get radicalized by your own audience. And obviously for Daily Stoic, I write about stoicism, but I write about the stoicism that I'm interested in writing about. And I insulate myself quite a bit from the day-to-day feedback of it. The feedback I do get tends to be from real people in person, like at events or on the street or whatever. you have to keep an arm's distance between the feedback or you do you're owned by it and directed by it yeah like i i think it's interesting like you don't you don't have the login for convert kit you don't see the daily like no numbers how many people are unsubscribing because of some email you wrote it's especially at a certain scale that's too much information for a human to be trusted with you know what i mean especially a sensitive human which you like i I think you inherently are if you're a creative person.

44:28Like, I know how hard it was to get one subscriber, 10 subscribers. I remember when we hit 1 ,000 subscribers. So I think, because someone told me this recently, I think like Daily Stoic does like 1 ,000 new subscribers a day or so, something like that. And then also a certain amount of unsubscribes a day, right? It's not a wash because it ultimately is growing every day. But the point is, I don't want to know that by writing about this thing, which I thought was important or I thought was good or I tried really hard on, I don't want to know that I lost 8 ,000 people. Do you know what I mean? That's not information that's conducive to me like having fun with my kids later.

45:09I'll feel like I failed in some way. I fucked up in some way. I'll be reluctant to talk about that thing in the future. You know, maybe there's some place where you stoically get utterly independent of, you know, caring what people think. But an easier thing is just to insulate yourself from what people are thinking. Yeah. You can also like take the wrong, you can tell yourself the wrong story about those unsubscribers. It may just be that they've been not reading it for a while and they're like, today's the day I'm going to, it had nothing to do with the actual content. Yeah, yeah, of course.

45:44They also could have been people who were fans for the wrong reason to begin with, right? Like you realize, oh, these people heard about me from this show that I did or this thing that I wrote, and they think that's who I am or they think that's all I am. So they became fans, which is great. Welcome. But only based on a partial representation. And now they have a full representation. They're like, it's not for me. well, I could feel bad that I'm not for them, but if they had never signed up in the first place, I would not think about them at all. So I, I, I, you know what I'm saying? Like the fact that I earned them and then lost them, it's the same as never having gotten them, you know?

46:27So I try not to think about it. There's this question, um, this guy, Nat Friedman has on his like about page, like, where do you get your dopamine in the process of what you do? What part of the process Do you love the most researching, the finding a story that connects to something that you're excited to write about, the actual writing? The most exciting part of a creative project for me, like a book, is when I crack it. Like I knew vaguely what it was going to be about. I knew vaguely when it was due. I knew some of the pieces that were going to be in it. But when a book that was going to be about humility or about how social media puffs us up, when that becomes ego is the enemy, and then I go, and then there's the beginner phase and the success phase and then how ego impacts you when you failed.

47:20You know what I mean? I took this enormous overwhelming thing and I fucking got it. That's the exciting part. When the book about temperance became a book about discipline and then physical discipline, emotional discipline, and then this kind of spiritual discipline. Like when that happens. When I was writing that book about Peter Thiel and the destruction of Gawker, when I was like, this is a book about a conspiracy. It's not a book about media. It's not a book about tech. It's not a book about power. It's a book about a conspiracy. What is a conspiracy? And how does a conspiracy work? And what do conspiracy, what is this have in common with other conspiracies?

48:01Not conspiracy theories, but like when a group of people conspire to do something behind the scenes that changes stuff, that's what, that's what I get excited. It's not that it's all disappointment from there, but that, that's like, that's the initial rush. And then the, then I have to go make that thing real. There's a dip there. That's the really hard part. And then at some point, you know, when you're maybe halfway or two thirds of the way done, when you're like, I'm doing it. Like when the house doesn't look like framing, it looks like a house. And you're like, oh, this is a nice house. That's exciting.

48:33That's the dopamine. I mean, I like doing all the individual pieces along the way, but the big breakthrough, that's the breakthrough that you live for. Yeah. You said that Ego is First, a book about humility. The proposal title was like something so bad. It's like embarrassing. And so I don't even know what it really was. Like it was very, it was, they were just like, sure, we'll buy another book from you. Do you know what I mean? Like, like I think they knew I didn't really know and they didn't really know, but they kind of wanted to lock me up and it took a while to figure it out. Steven Pressfield actually really helped me with it.

49:07But, um, yeah, it just took a while. But you first sold it as a book about humility. Yeah. Or it wasn't, I don't even know what I sold it about, but it was going to be a book about humility. That's what I was talking about. and then it was never a book about ego until it became a book about ego. How did you get to that revelation? Well, so with Ego is the Enemy, so I sold Obstacles Away. I was working on this book about humility. And I remember I was at Mike Lombardi's house, who was a GM for the Browns, front office person at the Patriots. He's the one that read the Obstacles Away and started passing away through professional sports.

49:41He had me out. I watched the Patriots game in the stands. I think I met some people from the team, and then I was at his house. We were watching some football. He's like, what are you working on next? And I was saying, you know, I'm working on a book about humility, I think. And he was like, oh, that's great. That's really important. He's like, he said, ego is the number one cause of unemployment in my profession. I thought, oh, that's really interesting. And then he, I don't know if he said ego is the enemy or he said, you know, ego is the problem. He said something, I was like, oh yeah, ego is really the opposite of what I'm talking about.

50:15and I'd read a bunch of books about humility and they weren't that interesting. There's a book called Humilitas. I'd read a bunch of books and not only were they not that interesting, but clearly they'd not resonated with a large audience. So it was like, okay, maybe this is the way in. And again, that's what gets you excited, like the way in. Yeah. Cracking the structure. Yeah. Obstacles Away was like the big one for me when reading it and just being like, wow. And when I reflect on it, there's something about the structure of that book that is so like perfect to the idea. Yeah. And the three parts, did you have that laid out in like the early stage?

50:50No. I mean, first off, I saw that book was called The Art of Turning Obstacles Upside Down or something, you know, like, so you have this sort of bigger, vaguer sense and you're boiling it down and boiling it down to its essence. And I probably told someone I was working and then they repeated that phrase back to me. Like I probably got that, that phrase from someone, but the three part, I mean, I think I knew I wanted to be a three part structure because that's like the structure of art in Western civilization, the three X structure in movies and in art TV shows or movies and plays and a lot of great books.

51:30So I knew I kind of, there's something about like the one, two, three. And, uh, and then I was thinking about sort of what the process was and right. There's kind of how you think about things, then there's what you do about them, then there's sort of, you know, wrestle with what happens, right? And there's kind of this loop. And then that's when I was reading something about the Stoics and someone pointed out that the three disciplines of Stoicism are the discipline of perception, the discipline of action, the discipline of will. And then I remembered there's a really great quote in the Hayes translation where Marcus goes, objective action now at this very moment, unselfish action now at this very moment, willing acceptance now at this very moment, that's all you need.

52:18I was like, oh, someone already solved this problem for me. You know what I mean? They already laid it out exactly. And so that became the structure. And then once you have the structure, then you can fill all the pieces in. Like one of the things Robert often talks about is his not being able to find a researcher since you and how he's had like dozens of them and they've just not been very good. What do you think makes a good research assistant? Yeah. Finding any creative collaborator or employee is hard. You know, I have a lot of people work for me over the years and like I count on one hand how many were like great.

52:54I've had a lot of research people. I've only had two that were any good, Christo and you. And I don't know exactly what separates the good from the not good. I mean, number one is like, you can't be crazy. Like, I mean, most people are nuts or just don't have their shit together. They're just not adults, right? So number one, you just have to have your shit together. Number two is you have to sort of intuitively understand what the person is doing. Do you know what I mean? Like I liked Robert's books, but I also got Robert's books. And if you don't know, you know, like if you're a personal shopper or a stylist and you don't fundamentally understand what the person you are trying to dress, like what the host of The Tonight Show can and can't wear, what they look good in or don't look good in, what they feel good and not good in, you can't do the job.

53:49Do you know what I mean? Your sense of style is not the most important thing. The ability to understand and be the representative, the decision maker for another person, that's the hardest and the rarest thing. And that requires a kind of humility and it requires an empathy and requires an interest, you know, and an understanding. And that's like, I think that's the rarest thing. And then the person has to be like, they have to have the chops, you know, they have to be able to research. They have to be able to think. They have to have a wide range of interests. They have to have drive. You know, they have to do all the other stuff.

54:26But I think those first two are probably the ones that eliminate 95 % of the people that I've ever talked to or Robert's ever tried to work with. Yeah. When I asked Robert, he said a couple of things. One was what you're describing about like not understanding the spirit of their materials, how he put it. Like they didn't get the spirit of what I look for in research. But then you said that the dividing line between success and failure is boredom. And these people are not able to sit with the boredom that is reading and going and looking for material. That makes sense. I remember Robert said to me, he was like, I'm like a shark.

55:03He was like, if there's one drop of blood in the water, like a shark can smell it. And he's like, I know if there's something in something. You just have this kind of vague intuition that there's like something in that, right? Like in this school of thought or that book or that story or that era of history. And it's something you cultivate over time, but it's also just, you just have to have a wide understanding of history and eras and people. Like a lot of my books, I'm writing about a topic. I've sold, the hardest part is the proposal because you're like, I'm going to write a book about this thing that I don't know that much about, but you're paying me and then I'm going to go figure it out.

55:42But I do have this fix, like I'm sitting down and doing the courage book and I go, okay, I don't want us all to be a bunch of like dudes riding into battle or, you know, climbing mountains or whatever. And I was like, who would be interesting? And I was like, Florence Nightingale, what was her deal? You know, like, and probably just was mentioned in some little book that I read as a kid or, you know, like it's just, I, you have kind of a photographic memory or a file of just like interesting ideas, people, things, you know. When I was researching for the 50th law for Robert Greene, you know, I was just like, I think there's a good book about this.

56:20Or what about this person? And I just kind of, a lot of what he was assigned to me, and a lot of those didn't have anything in him because if he knew there was something in him, he would have done it. And then I had the freedom to be like, what about this? What about this? And I, you know, it's like, there were also things that I was just interested in reading. I was like, I don't know anything about Eleanor Roosevelt. I don't know anything about Jack Johnson. And I would go research about, you know, that. And then I'd find something. And then, then you develop sort of a confidence. You go, oh, you know, you kind of have this tingly sense.

56:53Like there might be something here. And you're, you're okay being wrong, but you, you do find it. Yeah. I often think like one of, like the people we've, we've tried to help with research. which one of the things I struggle with is that feeling of spending a lot of time on something and it not being fruitful. Yeah, sure. Like reading a full biography, if like we assign that to him and there's nothing in it. Yeah. And it feels like time wasted. Yeah. And it's like, actually you saved us a lot of time because then I didn't have to read that book. Right. But, but you're, you still do that. Like you still read a book where it's like, I think there's going to be something here and I was wrong.

57:28No, and I get better at quitting books. Like I get better at knowing faster when there's not something in something. But yeah, I mean, there's a lot of dead ends, a lot of dead ends. Yeah. I guess the boredom is the dead end, the humility of like, could be wrong. And then you also just, you have a wide ranging of interest because it might not be good for this, but it's, you come back to it five years later and it's exactly what you needed to know. Yeah. John Mayer's got this analogy of like assembling firewood. Yeah. And like the times when, when you think you just waste a lot of time is actually firewood that like might be used later in a different project.

58:04Encourage is calling the third part of the book is about the 300 Spartans at Thermopylae. And I obviously had read Gates of Fire. I'd read different things about the Spartans. And I was like, I want to tell that story. I knew I wanted to tell this story. and uh i was like the original sort of source for the 300 spartans is is herodotus so i went and i got my copy of the histories which i'd read you know my early 20s and you know i look in the index where is it you know find it uh some page 400 or whatever and i'd read it before but when i opened it, you know, 15 years after I'd last touched it, I did not expect it to already have been broken down.

58:52And almost every quote I used in the book and the parts of the story that like I'd already done it. It was like time traveler. Do you know what I mean? Like I didn't know what I was using it for. I didn't know that I would use it. I didn't even really have any idea that I would be a writer when I read this. I would have read it since like 2005 or 2006 or something. It wasn't even a research assistant yet. Obviously, there's no real magic. When I read it and did that, some part of me must have thought I could use this. And that's why it was sitting in my mind when I was thinking of stories I could use.

59:26But I was just doing the work then following the process of like, this is how you read. This is how you take notes. This is how you identify things that interesting. And then I let it sit fallow for a decade and a half. And then it was exactly what I needed. And I think Adam Rubin, he writes children's books, but he was saying, that's the closest to time travel that there is. It's your ability to travel into the future and give a present to your future self, the stuff you do now or the things you accumulate now. And it's true. Like if you, if you want to feel good in a, I don't know, tight pair of pants or something eight years from now, it's like what you're eating and the work you're doing now is a result of that.

1:00:11Do you know what I'm saying? Like you don't want to have, I don't know, fucked up joints. Like you got to stretch now or whatever. So it's like the work you do now is a, is a form of time travel into the future. It's a gift to your future self. Yeah. It's sort of like the discipline now, freedom, freedom later.

1:00:32If you want to come see me talk, you want to see me get over some of my own stage fright, and you want to ask questions and hang out a bit, I would love to see you. I'm doing events in London, Rotterdam, and Dublin in early November. And then after that, Vancouver and Toronto. This is all basically the 12th through the 20th. So it's going to be a busy November for me. So grab tickets, ryanholiday.net slash tour. Both the events in Australia sold out. So these will sell out also. So grab your tickets. I'll see you all soon. Thanks so much for listening. If you could rate this podcast and leave a review on iTunes, that would mean so much to us and it would really help the show.

1:01:08We appreciate it. And I'll see you next episode.

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