The Daily Stoic - Turn the Tables | Ryan Holiday Reflects on 10 Years of The Obstacle Is the Way

Episode Date: October 9, 2024

Today, the tables have turned as Ryan Holiday is interviewed by his research assistant, Billy Oppenheimer, to talk about the 10th Anniversary Edition of The Obstacle Is the Way. They discussed why Ryan felt it was important to update and expand the book, what stories and pieces of wisdom were necessary to add, and the experience as a writer of revisiting material you wrote 10 years ago. Ryan also touched on the evolving reception of Stoicism and how his perspectives and writing style have changed in the process, providing a deeper understanding of how life's obstacles present us an opportunity for virtue as much as victory.Billy Oppenheimer is Ryan Holiday’s research assistant and the writer behind the newsletter, Six at 6 on Sunday. To read more of his work, check out his website billyoppenheimer.com.📕 Get a signed, numbered first-edition of the 10th anniversary edition of The Obstacle Is the Way by Ryan Holiday at dailystoic.com/obstacle✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/📱 Follow us: Instagram, Twitter, YouTube, TikTok, and FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Wondery Plus subscribers can listen to the daily Stoic early and ad free right now. Just join Wondery Plus in the Wondery app or on Apple podcasts. We've got a bit of a commute now with the kids and their new school. And so one of the things we've been doing as a family is listening to audiobooks in the car. Instead of having that be dead time, we want to use it to have a live time. We really want to help their imagination soar. And listening to Audible helps you do precisely that. Whether you listen to short stories,

self-development, fantasy, expert advice, really any genre that you love, maybe you're into stoicism. And there's some books there that I might recommend by this one guy named Ryan. Audible has the best selection of audio books without exception and exclusive Audible originals all in one easy app.

And as an Audible member, you choose one title a month to keep from their entire catalog. By the way, you can grab Right Thing Right Now on Audible. You can sign up right now for a free 30 day Audible trial and try your first audio book for free. You'll get Right Thing Right Now totally for free. Visit audible.ca to sign up. Hello, I'm Dak Shepard.

And I'm Monica Padman. Monica and I do three weekly shows with celebrities on Monday, experts on Wednesdays, and crazy stories from listeners on Fridays. We're so excited to officially be a part of the Wondry Network. So follow Armchair Expert on the Wondry app or wherever you get your podcasts and subscribe to Armchair Expert on YouTube. Welcome to the Daily Stoic Podcast, where each weekday we bring you a meditation inspired

by the ancient Stoics, a short passage of ancient wisdom designed to help you find strength and insight here in everyday life. And on Wednesdays, we talk to some of our fellow students of ancient philosophy, well known and obscure, fascinating and powerful. With them, we discuss the strategies and habits that have helped them become who they are and also to find peace and wisdom in their lives. ["The Last Supper"]

Hey, it's Ryan. Welcome to another episode of the Daily Stoke Podcast. I think I told you I was just in Brazil and it was very cool. I was not there for very long. I was there for like seven hours. It's funny, I posted a picture on Instagram of photo of me in a hotel lobby in 2012 in Brazil where I was there doing my first talk. And then this trip wearing basically, I think the same shirt. And yeah, you can see the age.

I mean, I've got gray hair, my face is a little more haggard. I think I've been better shaped, but what it took me back to in that hotel lobby and then looking at that picture is when I was in Brazil in 2012, I just put out Trust Me I'm Lying and I was negotiating with my publisher through my agent for the book that would become The Obstacle Is The Way.

And while I was there I emailed my agent and I was like, do you have the email? And he sent it back. Like the pitch email that we sent to Portfolio to write The Obstacles of the Way, which I think was called Turning Obstacles Upside Down or something. I hadn't even refined the title yet.

Didn't know what the book would be. I certainly didn't know what it would do. I didn't know that The Obstacles of the Way would go on to sell millions of copies, be in 40 languages, including it was cool to meet my Brazilian publisher while I was there and to give a talk when I was in Brazil the first time.

I think first time I'd ever given a public talk and now to have this experience under my belt. That's actually kind of what I wanted to talk about here because the 10 years plus since the obstacles way was sold and then came out, like I've experienced a lot. I've learned a lot. Life has inflicted a lot of lessons on us. We had a pandemic, I had kids,

I had businesses start and fail, I had conflicts, I had problems, I traveled the world, I learned a lot. And so I've been lucky enough now to do this new edition of The Obstacles Away. You can grab those signed numbered first editions at dailystoke.com slash obstacle. We sold out of them when we did this for Daily Dad

and we sold out for a right thing right now. And I think discipline is destiny. So those will definitely sell out soon. Grab those at dailystoke.com slash obstacle. But I was in the office on Friday and Billy Oppenheimer, my researcher and future author himself, he's working on a book. We were just chatting about some stuff.

He was asking me some questions because like the books had just arrived. I just recorded the audio book and he was asking me some questions. I said, you know what? We should just go into the studio. Let's just talk about this. We did a turn the tables episode a couple months back.

And I was like, I know you have some questions. I'll answer your questions and we'll just record it. And that's what today's episode is. You know, what have I learned in the 10 years since the obstacle is the way it came out? What have I changed? How do I think about the success of the book? How would I do things differently?

Just a bunch of awesome stuff. I thought it was a great conversation. We were gonna go for, I don't know, 30 minutes. We ended up going quite longer than that. I don't know if I'll cut this up, but we ended up talking for like 80 or so minutes. The only reason I had to go was I had to pick up my son from school.

I could talk about this all day. I really am excited about this new edition. I hope you check it out. And one thing I check out every Sunday, Billy has a great newsletter called The Six. It's six on Sunday. You can grab that at BillyOppenheimer.com just to give you a sense of that,

when Buzz Williams, the coach at A&M, was on the podcast a couple weeks ago, he was like, is Billy Oppenheimer here? Which I thought was pretty cool because he gets the newsletter. So check that out and then grab the new edition of The Obstacle is the Way. That's the 10 year anniversary edition.

Bunch of new stories, changes, improvements. That's at DailyStoic.com slash obstacle. Also, I'm not gonna be doing a talk in Brazil anytime soon, but if you wanna come see me in Europe, I'll be in Rotterdam, London, Dublin, Toronto, and Vancouver and you can grab tickets at ryanholiday.net slash tour. That will sell out as well, so grab those.

And I hope we can have a chat. I'm gonna do a bunch of Q and A's as well as part of those talks as well. So grab those and I hope we can have a chat. I'm gonna do a bunch of Q&A as well as part of those talks as well. So I hope to see you there. All right. So where are we starting? We're wearing matching shirts. Yes.

Not on purpose, but here we are. What if we started with, like, I imagine there's a lot of people who this book means a lot to. Yeah. It means a lot to me. It was a really impactful book at various times in my life. And if somebody thinks, well, I've read that book. Yeah.

Why would they want the 10th anniversary edition? Well, you know, I feel, I've read that book. Why would they want the 10th anniversary edition? Well, you know, I feel like I've read that book because I wrote it. And then I had this unique experience during the pandemic where I was reading some of it to my son, mostly to put him to sleep. And because if I read him stuff he was actually interested in, he would just stay up.

And so I was reading it. And I was struck by just like how different it was from how I feel like I right now. Like there was none of this bad in any ways, I was obviously very proud of the book. But there were just things that I wouldn't let myself get away with now. Like I wouldn't I wouldn't say it so I wouldn't say certain things so unthinkingly or unfeelingly or so, I don't know, directly. Like I would qualify the statement more. I just have more context. I have more understanding. And in Ego's Enemy, I have this whole chapter

about Ulysses S. Grant that certainly reflects my opinion of him then, but if I was writing it now, it would be very different because I have a better opinion of him. The central point still stands, but I would rewrite it if I could. Yeah. And so with the 10 year anniversary coming up, the publisher asked if there was anything I wanted to do. And I said, Why don't we just do like

a whole updated edition? They were excited about that. Also, because 10 years ago was long enough that audiobook rights were very different. And they kind of sold the audiobook rights for a few pennies to Tim Ferriss. He's the reason the book blew up. But then those rights reverted back to the publisher. And there was a thing about, do I have to rerecord it? Do they buy the old audio from him? So there's a bunch of stuff swirling around about like why or that it would be nice to get another crack at it. And on all my books, I keep researching even after I stopped writing. And so I had to also

just a big stack of note cards of like things that in some cases proved the ideas I was talking about more just additional examples, additional stories. And so I Yeah, I got to have this weird experience of like, it's almost like exhuming a corpse or something like, all of a sudden, this thing is in front of you. And it's in some cases aged well and other cases not aged well. And I did this on I did this on trust me, I'm lying also, but I think it was like a five year anniversary

edition because like, stuff in the media changes faster than this. But I don't know, I really wanted to just make it better. And I wanted to also reflect, like who I was writing the book at 25 is very different than who I was rewriting it late 30s. So I feel like it's better. And I feel like there's this stoic idea that we don't step in the same river twice.

And nothing illustrates that idea more to you than rereading something that you wrote and then editing something that you wrote a long time ago. Having to listen to the audio book of The Obstacle is Away and barely recognize the voice of yourself, that is a surreal kind of mind fuck of an experience. Like doing an audio book is already a strange feeling. I learned that when I was doing the audio book

for the obstacles away, the way you hear your voice is it like rattling around through your skull, I guess like when it comes out of your mouth. And then when you listen to it on headphones, we listen to it recorded, it sounds very different. And so doing an audio book or a podcast is already strange because you're like, oh, that's how I sound. But to listen to an audio book that you did 10 years ago,

where you were as a writer 10 years ago. So for me to listen, not just to an audio book of myself, but an audio book of myself as who I was in my early 20s. You're barely recognizable, because that's the idea that we never step in the same river twice. That book that I'm rereading now, I interpret differently and the ideas in it, I interpret differently.

And so I just wanted to update it and change it and make it more reflective of who I am and what I feel like it means to me now. Like the saying, the obstacles away. I think in my early twenties, I was thinking about it primarily as a, this is how you overcome professional obstacles. And what that idea means to me now

is a deeper, more personal thing. Yeah, you talk about a little bit in the new prologue to the- Well, the book already has a preface. So we're like, you talk about a little bit in the new prologue to the... Well, the book already has a preface, so we're like, what is it before a preface? The reflections. Yeah, yeah, yeah.

And what you sort of left off that phrase, like... Yes. Well, first off, when Marx really says, our actions can be impeded, but there can be no impeding our intentions or dispositions, because we can accommodate and adapt, the impediment to action advances action, what stands in the way becomes the way that quote, he's specifically referring to difficult people, which I think is interesting.

But as I talked about it in the book, I was talking about it primarily as it relates to like professional obstacles of which people are often a source. But when he's saying the obstacles away, he's not saying that everything is this chance to just like, move forward or get stronger or make more money or something. Like he's not just talking about it in a sort of a professional context.

When he says everything is an opportunity or that there's a chance to advance, I think he means in a more profound sense that there's always this chance for us to practice virtue. So difficult people, in the ancient world, a difficult person could throw you into exile as Seneca experienced, could throw you into slavery as Epictetus understood. A difficult person could attempt to overthrow the kingdom as Marcus Aurelius experienced. So what opportunity do those difficult people present?

I think Marcus Aurelius was saying that they present an opportunity to practice forgiveness. So in his case with Avidius Cassius, a chance to practice forgiveness. In Seneca's case, it's a chance to sort of toughen himself up. In Epictetus's case, it's his chance for him to understand this deeper level, like where freedom actually lies, and it's not in external things, but in ourselves. So the idea is that obstacles

are always the opportunity to practice virtue, as opposed to obstacles are always the chance to spring forward professionally. They often can be, but I'm reorienting the book a little bit more around that deeper idea. Yeah. When you go through the book, how do you determine what you wanna change and what stays? There's a bunch of very specific things that I had notes that I wanted to change.

And then I kind of, you know, every day I was working on it, I would just open it, flip to a random spot, and then just kind of reread it and ask myself, hey, is this how I would say this now? How could this be said better? What is this missing? So a lot of times it was stuff like that. And then on the, even during the audiobook, which I just did in this chair, having to say every word of it out loud was like an an excruciating experience because I hadn't done that for 11 years. And to go through and have to say things that you put into print. A decade ago, there's a Seneca thing he says,

when I think of all the things that I have said, I envy the mute. And the experience of editing something you've already published, or re recording the audio book of something that millions of people have listened to. I mean, it's horrifying because you go I said that like, I, I allowed myself to leave it at that. And I mean, not everywhere, there's lots and lots and lots of parts of the obstacles,

which I'm very proud of. But if you can reread something you wrote or worked on a long time ago, and you think it's perfect, I mean, to me, that's a sign that you haven't gotten any better since you've done it. Like the idea that you don't have improvements to make, to me would imply that that was the peak, which I definitely don't think is true and I definitely don't want to be true.

I mean, what was the point of continuing to do it if you're not getting any better? I always think you have a unique relationship to your work and that it's like a lot of your favorite stuff as a reader that you're bringing together. Sure. And the experience of going back and looking at a lot of those stories, I imagine was like, I actually think the lesson embedded in that story is different than I initially thought. Yeah, well, that's the idea. And they say, No, you know, it's up in the same room twice. That's the other part of it is that what stands out at you in a specific story is

different. And yeah, the meaning of it can be different. So yeah, like when I talked about Rockefeller at 24, I'm just thinking of him and I'm only thinking about him in the context of how did this guy overcome obstacles? I'm only thinking of the heroic aspects. But then the book I wrote immediately after was about ego. And then I wrote a book about stillness. And then I've written a book about discipline. And then I wrote a book about justice. And so if those subsequent deep dives into topics

don't inform your worldview going forward, what does that say? And so now, and of course I understood these things about Rockefeller, but that wasn't what I was focused on. Those weren't like the salient things that were jumping out at me. your worldview going forward, what does that say? And so now, and of course I understood these things about Rockefeller, but that wasn't what I was focused on. Those weren't like the salient things that were jumping out at me. But now looking back at this person and my own writing,

and what I want the book to mean to people, you're adding on these additional layers. And I think the portrait that I present of him is more nuanced. And then also just on top of this, I've had a decade more of reading. So I've read more like my stuff on Ulysses S. Grant, my stuff on Lincoln in this book, I think are much better now, because I've read literally thousands of pages about their lives and the time that they lived. And all the while I was making, oh, that's a perfect obstacles away thing that I want to add in there. And so I just, yeah, have these like, it's like comedians talk about tags, which is like a thing at the end of a joke.

There's a lot of little tags or little extra layers or an additional detail that I wanted to little extra layers or an additional detail that I wanted to put in there. In the prologue or the intro of this book, you specifically talk about or sort of anticipating a lot of people's how they associated the word stoicism 10 years ago. Yes. And the work you've done since then to make that word mean something very different to a lot of people now? Yeah. I remember when I was writing the book, the Stoicism subreddit on Reddit had like 9,000 subscribers. And I think it has like a half a million now,

some crazy number. And so, yeah, when I was writing the obstacles away, it was, hey, let me tell you about this thing called Stoicism. And the task was much more along the lines of popularizing and making interesting a thing that a lot of people did not think was interesting. And then one of the tricky things about success

is if you succeed, the original context in which you were operating is obliterated. And so, the idea that Stoicism was this unattractive or uninteresting thing to people no longer exists. And so, I think that's something else I wanted to very much address in the book. I'm not, I'm now obligated and able to give a fuller picture of the philosophy that of a fuller picture of the philosophy that I think is more urgently needed than it was then if that makes sense. Yes.

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Or Esther of Burundi, a princess who fled her home country to become France's first black supermodel. There's also Queen Christina of Sweden, an icon who traded in dresses for pants, had an affair with her lady-in-waiting, and eventually gave up her crown because she refused to get married. Throw in her involvement in a murder

and an attempt to become Queen of Poland, and you have one of the most unforgettable legacies in royal history. Follow even the royals on the Wondery app or wherever you get your podcasts. You can binge even the royals ad-free right now on Wondery Plus. You talk about in the reflections thing about when you first went to the publisher, you've since learned that they hoped you would get this ancient school philosophy book out of your system that first time. I mean, I know you couldn't have imagined it how it played out, but what do you think

in hindsight was like the reason it landed and became such a sort of phenomenon in the way it has? I mean, look, I think part of the reason it worked is because it shouldn't have worked. Like in marketing, they talk about sort of counter programming. Like when you're the opposite of what everything else is in that moment or in that niche or space, it stands out. And the idea of an obscure school of ancient philosophy

being the core argument of a self-help book or a business book. I don't know. Let me see actually. I think originally, I don't know what category it's in. Books used to say, now I'm like an old man. I don't know what category it was in. But originally, The Obstacle's Way was in the business category. And so it very much stood out even like self help as a big category wasn't as popular then. So I do remember getting a surprising amount of media attention compared to what people thought it would get because it was so unusual and weird. And that was

probably the first like seven years of attention for it was like, this is weird and small and unusual. And then at some point slowly that flips to like, now this is big and popular and there's a backlash about it. But I think the publisher was just taking a chance. So in publishing, when you sign a book deal, typically they have the right of first refusal on your first book, or on your next book. It's called they have the option. That's what your publishing option.

And so I think they were like, okay, this first book did okay. This second, we, we don't want to pass outright. But like, by nature of what they offered, they were, I can tell they weren't that excited. It was like something like half of what I've gotten from my first book. And so I think they thought downside is relatively low, upside, whatever, you know, like if anyone had thought this is what it was going to do, then either they were playing their cards very close to the vest, or somebody screwed up. I know they didn't think it because I didn't even think it and the idea that they would have had bigger expectations than the author is

probably unlikely. Someone else told me later to that they thought their prediction for the obstacles away was that it would sell like 5000 copies. And I thought this person was my friend. So that's not a nice thing to say. But I didn't think it would sell that few. But I wouldn't have said it would sell 100 x that you know, I didn't think that I don't even think I thought 50 x that I wasn't thinking it would be a home run. I thought it would be a solid single

and that's all I was thinking about. Yeah. One of the new stories in the new edition is about Taylor Swift. And I'm wondering, because I know you like to err on the side of older figures. And I was wondering about the decision making process to include a contemporary person.

Well, one of the big flaws of the obstacles away is that there's just not enough female stories in it. They just like, that's a criticism I got from many people over the years. And they were totally right. I just didn't have that many like I hadn't been doing this very long. And so my sort of like, my repository of things to draw on was just I mean, Amelia Earhart's in there and Laura Ingalls Wilder is in there. And I think Margaret Thatcher is in there. There's a couple other

examples, but there, there were not very many, like, big stories about female protagonists. And the periods you like to read about, there's just not a lot written about. True. But I wouldn't let myself out the hook that way. There just wasn't, I just didn't, just didn't have the stuff, you know? So that was definitely something I'd always planned to fix if I ever got to redo it.

And I told that story, I gave a talk to Five Nation last year. And whenever I give talks, I try to draw something from their world that will illustrate the ideas. And so I was like, oh, I'll just tell this Taylor Swift story. Cause I do think it is really interesting. Here you have this person who was a huge

musician, but not like the biggest act in the world by any measure. And someone she doesn't like buys her masters. And she has a couple of options. I mean, one, she could shrug it off to she could try to buy them herself, they would have cost a couple hundred million dollars. She I don't think had. She could have just been pissed off. She could have been angry. She could have filed a bunch of lawsuits. She could have played like this sort of pity me public relations game. And instead, and you can trace it all back to this tweet from Kelly Clarkson, which is pretty crazy. Kelly Clarkson is basically like, look, why don't you just rerecord all your music, do new album covers, add some new songs, and

let the fans support you? And that's what she did. And I don't know if she could have possibly conceived of what would happen, but she put in motion a plan that catapulted her from a very large musician to one of the biggest musicians in the history of music. And if you think about what the era's tour is, the biggest tour of all time, even the movie about it's made like a couple

of hundred million dollars, that's a result of her having basically continually put out music almost on a monthly basis for the last five years. And a new generation discovered her stuff, an older generation rediscovered her stuff. There was endless amounts of publicity and attention, drama, spectacle. And I think to me, just as a marketer, what was so fascinating is like, how she managed to take first off,

like the definition of a first world problem, like a hedge fund buys your First off, like the definition of a first world problem, like a hedge fund buys your catalog worth millions of dollars, from the other company that owns it. And you somehow figure out a way to let that make you the underdog and that like people should be rooting and cheering for you. It's like, it's insane.

The unlikeliness of that is pretty incredible. The other interesting thing has been the number of people who've told me they've had their teenage kids read the books. And so I was like, okay, let's put a story in there that isn't some old dead white guy that they have in. Right. It just made me think of what you're describing

about the original impediment to action quote about being, how do you handle people? Yeah, she doesn't like this guy who I actually know and has been very nice to me over the years and has read and sort of talked about the books. So the funny thing was like, I'm sure he didn't like that story. When I, they posted a video of that clip

when I talked to Live Nation and it got a lot of attention. And I doubt that was fun for him, you know? But you don't have to like the protagonist of the story to understand what they're doing in the story. That's the other, the email, I'll get them, I'll probably get one of these a week. Someone will read, I tell the story of Obama in the 2008 campaign,

and the, the more perfect union speech where he basically takes the Jeremiah Wright scandal and he flips it into this incredible speech that sort of catapults him to the nomination and then the presidency. And then people go, why'd you put this Obama story in there? And I go, you don't have to like him to understand that this was an act of political jujitsu without precedent that like this guy took not just

a potentially campaign ending scandal and survived it, but seized the offensive because of it and turned it into not just like a campaign defining moment, but actually like a country defining moment. That speech is one of the greatest speeches on race in American history. And he used that. He called it a teachable moment. And that even that expression has become a bit of an expression. So there's this meta level where just the idea of teachable moments becomes a thing. So you don't have to like the person to benefit from the story.

And I think this is true across the board in the obstacles way. Like you can think that John D. Rockefeller is a rapacious robber baron who destroyed the environment, or you can hate Samuel Zamuri for the destruction and chaos that he sowed in Central America. And you're probably right on those things, but that doesn't mean that there's not a lesson in how they did things. And I would say that when I was writing the obstacles away, I was much closer to my time having worked for Robert Green. So I would say I was also more amoral in not immoral is the distinction Robert Green makes. But Robert Green says, you know, there's a difference between an amoral story and an immoral story.

An immoral story says, here's this fucked up awful thing. You should do this. And an amoral says like, here's something that happened. You should understand it. And I would say that the first draft and then ultimately, I got published of the obstacles was more of an amoral book than I would do now. And I would like to think that the updated edition, there's some people I got rid of, there's some qualifications I added. I wanted it to be a more well-rounded look at the characters than I did,

again, when I was in my early 20s. Yeah, do you wanna talk about anything you cut? Well, I mean, I can't hide it. It was in the first book or not, but I was fascinated by Erwin Rommel, the German general and military historians have always been fascinated with him in the same way that they're fascinated by Stonewall Jackson or Robert E. Lee. And so I told the story of sort of his approach to not leadership so much as his his sort of initiative on the battlefield, which I thought had some lessons. But, you know, as I got older, I was like, if that's the only way I could tell

that story, then I would have let it stand. So I was like, oh, this is very replaceable. And so that was a change that I replaced him with Patton, who by the way, himself is problematic, right. And so so like, I think that's an important lesson when you study history. There are no perfect characters. Not even Marcus Aurelius or the Stokes are perfect. So your understanding of the people,

you get more and more layers to them. But that was like an easy one to swap out. It was like, why leave this? In retrospect, I'm a little baffled that they let me put it in. Like nobody, I think it's, again, you go back and you just like, you wonder about things. Like, I mean, that book went through multiple rounds

of edits, multiple, you know, nobody was like, hey, you know, not that it's their fault, but I'm just saying like, it's not like, it's, you know, we talked about this last time, Kristi Noem, she killed her dog, they cut that out of like, she did a first, she did a book and someone was like, Hey, I think it's a bad idea to talk about killing your dog. And then she fought to put it in the next one. And then it blew up in her face. But I just nobody was like, Are you sure you want the

story? It's not like I was glorifying his abhorrent political beliefs or his associations with Nazism. I was glorifying his abhorrent political beliefs or his associations with Nazism. I was and I talk about him positively at one point, and then I have him be defeated by the American forces in subsequent chapters. So it was a it was a loop I closed off, I didn't just leave it hanging there, even in the first draft. But in retrospect, that probably should have been a discussion. And so now today, when people are like, oh, political correctness, what's all these sensitivity readers, which is something like they'll do in fiction books these days.

I'm all for it because anytime someone can give you a perspective that you're not considering or a view on something, you don't have to listen to it. But it is good to be like, hey, are you sure you know how this is going to play? Have you thought about how this is going to age? Have you thought about how this might be heard or felt by audience different than you? So yeah, I'm like, it's not like I wouldn't say I regret including it. But like, clearly, I'm not including it anymore. So tells you something. Yeah. Do you think it was? That's a reflection of what they thought the book would do?

I think they just didn't care. Yeah, that's an interesting thing. When you're writing, you're thinking like, I hope someone reads this. It's probably would have been delusional. I joked about this when I gave my talks in Australia earlier this summer. I was like, if I had predicted any of this for the obstacles away, I shouldn't have been allowed to write Ego is the Enemy. So like for me to go, hey, how is this gonna play if the book sells millions of copies? That would have been insane. So I wasn't sensitive at a level that ultimately probably demanded,

but you learn but you learn. Do you think now the awareness that there is that large audience, how do you think about like not letting that get into your process? Oh, that's interesting. Yeah, you wanna be cognizant that the audience exists, but you can't be paralyzed that the audience exists.

And there's kind of attention to that. I think I've mostly tried to incorporate it in positive ways. So by that, I mean, I've met lots of different people from different walks of life. In the course of writing the books, like people, okay, so then you meet someone who's like a general who's read the obstacles away, or you meet someone who's a head football coach, or you meet someone who's like a general who's read the obstacles away, or you meet someone who's a head football coach, or you meet someone who's going through a cancer diagnosis, or you meet someone who's a police officer,

or you meet someone who's a 16 year old kid and their parents made them. So you meet these different people and then they can kind of serve as avatars when you're doing future projects, or in this case, when I'm coming back to it. You just have a better sense of who is on the receiving end than you did before. I'm writing in this case, when I'm coming back to it, you just have a better sense of who is on the receiving end than you did before. I'm writing about this now, I guess I could have put

it in. When Lincoln was president, basically anyone could just go to the White House and get a appointment with the president. And like the bane of his existence or the bane of his advisors existence was that he would have he spent like hours a day just like receiving visitors and each person would get like five minutes. It was just crazy, you know? I mean, this was the system until, is it Garfield? Who were the two presidents assassinated? Garfield and who was the other one? I don't think it was Garfield.

Maybe it was. Is assassinated by a job seeker who gets rejected. Like he meets him, asks the president for a job, the president says no, and then that's why he kills him. So Lincoln's advisors wanted him to get rid of this stuff, but he called them his public opinion baths. So he thought it was like this way on a very consistent basis to hear directly

from the American people. And that shaped and informed where he was on the slavery issue, where he was on recruiting, just like how that informed his messaging. And so I think if you just think about it as this large mass of people that probably becomes intimidating or becomes puffs you up. But if what you take from knowing about the audience is like the different types of people and the spectrum they occupy, it allows you, I think, to... I always just try to think, like,

how does every book at least have one or two nods to all the different types of people, you know? So if you're like a mom, you're reading it and you're like, oh, that specific thing spoke to me, so like the whole book speaks to me. I think you got to be able to like kind of imagine who is on the other side. It can be paralyzed by it, but you do have to have a sense of it.

Has there been a most surprising sort of testimony of from a reader that got a lot out of the book and applied it in a way that you thought? Well, there's a weird one. I interviewed General H.R. McMaster, who is the national security advisor for Trump. I think a three-star general. And we got connected by someone and he said, "'Oh, I've read your book, The Obstacles of the Way.' And I said, "'Oh, that's insane.

How did you hear about it?' And he told me that like some Arab king or sheik had given it to him." So like the idea that this book of Western philosophy came to one of the most influential advisors to the most powerful person in the world via like head of state or influential leader in the Far East is like crazy, you know? But again, you're just like, oh, you make a book and you fling it out into the world and you don't control where it goes or who gets it.

But to me, that's the power of stoicism is that like, in some sense, even though all the people involved in that live very different lives, they're all dealing with the same stuff at some fundamental level too. Like a world you don't control, other people, adversity, difficulty, stress, fear, temptation. Yeah. It slots in there.

I heard you say recently something about realizing that Zeno to Marcus was like, for Marcus that was ancient history. You know? Yeah, no it is. So if Zeno is discovering Stoicism between 400 and 300 BC, and then Marcus Aurelius is discovering it between 100 and 280, that's hundreds of years. And that's hundreds of years.

It would have been, so Stoicism would have been ancient philosophy to Marx's theory. We think they were like hanging out together, all the ancients. Yes, we think of ancient philosophy as this period. It's like the dinosaurs lived for millions of years, tens of millions of years between all the dinosaurs. Like old enough that there would have been like

fossils of dinosaurs while they the dinosaurs. Like old enough that there would have been like fossils of dinosaurs while there were dinosaurs. You know? And so the idea, Mark Sturios in Meditations quotes Euripides, this Athenian playwright. And he quotes a play that was lost. So you go, oh, okay, it was lost. But it must have been like a contemporary play to him.

That's why it's not lost. Like he quotes this play and we don't know, we don't have that play. So we go, oh, okay, so it's lost. So we go, oh, but he must have like seen it in the theater when it came out. Euripides was to Marcus, what Shakespeare is to us, like 500 years.

So think about how good or salient or popular that play must have been. And then also just how much history that is. It's 500 years old by the time it gets to Marcus Aurelius. What Socrates was to Marcus would have been like someone from the dark ages or the middle ages was to us, like just incomprehensibly distant. But Greece was still there and still the seat of philosophy in a different way than it is to us. But they were chasing classical wisdom in the same way that we're chasing classical wisdom.

Marcus Aurelius didn't think that he lived in ancient Rome. Marcus Aurelius thought that he lived in the future. You know, he was in the cutting edge. Mirrors were invented, like the technology for making like a great mirror. That's like a technology he experienced in his lifetime. But there would have been all sorts of things. Like he would have thought he lived

in the most cutting edge futuristic society that had ever existed, the most stable, whatever, which he did in many ways. And then at the same time, he's looking back at ancient Greece as this model, this golden age that could be learned from, whose values were urgently needed in today's society, which to us is 2000 years old. Yeah. And the timelessness of that is surreal. Right. The filtering of time that has happened. Where does he get the European quote? No, I think it would have just been an old famous play in the same way

that Shakespeare is still around. They would they kept them on these little papyrus roles. Actually, I just read this book called Papyrus, which is incredible. All these things were preserved in the Library of Alexandria or and there was another library in Pergamum. Like, these were just that was literature. Tanner Iskra So it wasn't he wouldn't have picked it up word of mouth because you said it was lost. David O'Brien No, what I'm saying is that play is lost to us today. So we think it's obviously lost

since Mark Surreal. I swear he wouldn't be quoting from it. But like, it was hundreds of years old by the time that he got it. It could have been lost two days after Marx found it. You know, like it could have burned in the burning of the Library of Alexandria. I don't know, but I just think it's, we think that these things, it was like they were new, and then there was the Dark Ages,

and then there was the Enlightenment, the Renaissance, the Enlightenment, and then today. But that period of classical Greece and Athens is hundreds of years old. You've also talked about relatively recent realization of like when Marcus is talking about the plague, he's not using it like, he's talking about what he was living through.

And on your earlier reads of the book, you thought he was like in the way we think of, we thought of it pre-pandemic. Yeah, it was like that quote, when the student is ready, the teacher appears. I think that's kind of the idea in that you don't step in the same room twice. You can only understand certain things

when you've been through certain things. And the understanding that the plague would have been, the Antonine Plague would have been, not this like background thing but like the most consequential event of his life and what it would do to people and how it would destabilize things and change things you can really only understand that when you have been through one so imagine somebody reading Marcus Rielis in 1922 coming out of the the influenza or somebody reading Marcus Aurelius in 1922, coming out of the influenza,

or somebody reading Marcus Aurelius after one of the bubonic plagues, or a smallpox or a typhus outbreak. You know, then you read them in 2020 or 2021, you go, oh, okay, when Marcus Aurelius says that there's two types of plagues, there's the one that can kill you, and then there's one that can warp or deform your character,

you have a sense of what that means because you saw it happen to people that you know. Either people you know died, or people fucking lost their minds, and it changed them, you know? There's people who are gone post pandemic, but still here. Yeah. And I think that's what he's saying.

Do you think the events of the last three, four, five years, how did that impact people coming to the book? Oh, sure. I mean, the pandemic was obviously a huge inflection point. Like you can look you can look at sales of Marx, Ruelis' meditations and like, you know, they're sort of flat and then the obstacles way comes out and they spike a little bit over the intervening years. And then in 2020, they just like go through the roof. And I think that's the timelessness of stoic philosophy. That's the algorithm of social media. You know, this thing being long

underground and finally kind of exploding. So it's a algorithm of social media. You know, this thing being long underground and finally kind of exploding. So it's a bunch of things, but the irony is, okay, so you're March of 2020, and all of a sudden bookstores are closed, all speaking stops, in-person podcasts stop. You know, publishers were clawing back advances, books were getting canceled.

As an author, you're like, this is the worst thing that could possibly happen. And then within like a few months, actually what happens is this explosion of book sales generally, like book sales have been on a tear since the pandemic, but then specifically Stoicism has this enormous resurgence. So there is something ironic about even the

way that the obstacles the way is introduced to a whole different audience, because this terrible thing happened. Now again, this is one of the I think, I think people miss in the book, you wouldn't trade for it. It's not you didn't want it. people miss in the book, you wouldn't trade for it. It's not you didn't want it. And if you were asked, hey, was it worth it? Again, no, that would be insane. You know, but there is what you managed to get out of it since it did happen. You know, I've heard Jerry Seinfeld say like if he could somehow take all of his experiences and trade

them, the only ones he would keep would be like the failures. Really? Because those are the most valuable. Yeah, I don't know. No. Would you? When I think in hindsight, like I don't really think of great moments. I guess.

I don't know. I remember when I was interviewing Peter Thiel for Conspiracy, he was saying that there's sometimes this like fetishization of failure when like obviously success is better. Like, you know, the Stokes talk about this idea of like, if you had to choose, what would you choose? I think I'd

probably choose the good stuff. But the whole point is that you don't get a choice. Yeah, you do choose whether you get something out of the failure, though. You know? Yeah, I swear to when he said it, it made me think of and you have this this quote in the reflections part, the Borgers quote. Yeah. And just like how those things are like what we ultimately use in our work. I get, yeah.

So there's a Borges quote that I love where he's saying that like the job of the artist is to take everything that happens to them and transform it into their work. That's what art is. But I think you can also do that with positive wonderful experiences too. But the point is you don't get a choice. Like sometimes it goes your way, sometimes it doesn't. And your job is to take that. And that when the Stokes are saying that everything

is this opportunity to practice virtue, obviously obstacles are particularly salient example of that chance, but success presents certain obstacles too. So Marcus realizes thrust into this position of immense power and responsibility. That's an incredible gift, a stroke of good fortune in one way, but it's also an incredible burden and responsibility in another. And it is precisely the privilege and the power and the immensity of it that demands the excellence and is the opportunity. And so, like, sure, if the obstacles away had failed, and been there, and you're like, oh, I'm going to be good, but I'm going to be good, but I'm going to be good, but I'm going to be

good. And so, you know, I'm going to be good, but I'm going to be good. And so, you know, I'm going to be good, but I'm going to be good. And so, you know, I'm going to be good, but I'm going to be good. And so, you know, I'm going to be good, but I'm going to be good despite this abundance and success. And so like, sure, if the obstacles away had failed and then this, you know, embarrassing, painful, devastating thing, then yeah, the obstacles away would have been a chance to practice stoicism.

But also the success of it, which was more than I could have possibly expected or felt was even within the realm of possibility. Well, now, you're challenged in all these ways of like, okay, you have to follow it up. You have to stay disciplined. You have to not let it go to your head. You know, you have to, you learn all these lessons about yourself. It's, the idea is that everything is this chance to practice excellence. And sometimes the obstacle is going to be, yeah, somebody stole from you, somebody

lied to you, somebody humiliated you, somebody broke your heart. But then sometimes the obstacle is, you just won a Super Bowl, and now everyone has extremely high expectations and the team is coming apart and you have to try to repeat. That's also an obstacle. It's a nice obstacle, but it's not like easy.

And so the idea is that every situation, good ones, bad ones, big ones, small ones, they're this opportunity to practice for that to me is ultimately what means to say that the obstacle is the wife. Yeah. As I was looking into the wooden stuff for. Yeah, the George Ravling book. Wouldn't have this line about he wishes all of his best friends would win one championship and all of his enemies would win multiple. Yeah, because it's destabilizing and overwhelming and can bring out the worst in you. More often than not, do people wear success well?

More often than not, does success make someone better or worse? More often than not, does success make someone better or worse? More often than not? Does power corrupt? Yes, it does. More often than not, winning the lottery turns out to be bad financially for the people who want it. That's crazy. Like you wouldn't think that's true. And it probably shouldn't be true. But that doesn't change the fact that it largely is. And so we sometimes think of, and naturally we're much more sympathetic to the person who overcame discrimination, the person who overcame a disability, the person who overcame incredible odds, but the odds aren't that great

for repeating a championship, for repeating on the best seller list, for maintaining any level of excellence or dominance in a given field, or I mean, the odds aren't even that great for like marriages and stuff, right? So like these wonderful things also present obstacles and challenges. There's also a weird thing where like,

no one wants to hear about your successful problems and how much money it's but it's like a real, it's a real thing. So what, what do you did it? You sold a book, right? People don't know Billy's sold his first book and he's working on it. That's wonderful. Exciting. You like you submitted a proposal and the publisher bought it. Huge accomplishment win that relatively few people ever get to say that they did. But it's still really fucking hard to then deliver on that thing.

And then it's even rarer that somebody who like gets across the finish line with the book has a successful book. And then how many of those people followed that book up with another successful book. And then how many people rare among all of those, like, don't become an asshole, you know, whatever, right? So it's, it's like a series of un behind mountains. There are more mountains.

That's a proverb I have in the book. It's hard. It's really, really hard. And the success or winning is you never just get to this point where you're like, and I'm through it and now everything's easy. Oftentimes it going exactly the way that you want it to go is entry into a series of challenges

that you could not have possibly even conceived of existing. You're right, the easiest part or the hardest part began after the proposal for sure. Yeah. In Ego's Enemy, I have this quote from John Wheeler, the physicist. He says, as your island of knowledge grows, so does the shoreline of ignorance. And as I've experienced that, as I'm not like exploring the frontiers of physics, it's just that every time you learn something or you do something, you find yourself in new territory that you didn't know that you didn't even know about.

You're like, oh, I didn't understand that's what people over here were doing, or I didn't understand that that's how that worked. And so it's this process of like, you think, okay, I just gotta get to here. And then you get to here and you're like, oh, I didn't realize like what was on the other side of that hill was just Like a bunch more hills. Yeah, I've also the book is like so different from what was in the proposal

Yeah, and I for a while was like aware that I wanted to go in a different direction from the proposal but I had this like block of being locked into what I sort of promised yeah and getting through, ultimately having a conversation with the editor and she was very supportive and liked the new direction, but I had this block of like, why I sort of promised them this one book and now I'm, as I've spent more time with the material, I see it's like a very different book

than I thought it was gonna be. Well, yeah, how could you have possibly, you'd only done a fraction of the thinking that you would ultimately do about this topic. You know, investors I think are better at this even than people in publishing, although people in publishing are familiar with it at some point, but it's like, it's not even a plan.

Your business plan is like a hypothesis and that hypothesis can be disproven like very quickly. And so you, yeah, until you've done it a couple of times, you just don't understand that you didn't understand when you started. How do you, when you're starting on a book now, versus like if you think back to when you're starting obstacle or ego, and what did you learn about like,

that's not something I'm gonna do in the next- I'm just much more comfortable now on books knowing that I don't know where it's gonna end up. And at the same time, much more confident that I know it's going to end up, if that makes sense. So like, I trust the process because I have actually been through the process a lot of times and I trust the process more than I trust the process because I have actually been through the process a lot of times and I I trust the process more than I trust myself.

So I just know, hey, if I just like keep showing up and I do like the next right thing and I just spend a lot of time and energy on this, eventually I'll solve all the problems and get to a completed thing. But right now, I don't even know what all the problems are because I haven't gotten there. And I'm just much more comfortable with ambiguity and unfinishedness than I was. Like I'm finishing, I'm on basically probably got like 10% left of the first draft of the fourth book in the Virtue series.

And I'm much more comfortable, like the last big chapter in the book is actually the first chapter in the third part. And I had a sense of what I wanted to say and I said that. And then I knew it wasn't good enough, but I was able to be like, I can just put a pin in this and go do all these other things. And that will allow me to come back later

and finish this part. As opposed to earlier on, I needed to like do everything consecutively, and I couldn't leave like big holes or structural issues because I felt like the whole thing would collapse. And now I can just kind of go, I'll do this today, I'll do this today. You know, I'm just like, I just have a better sense of,

I don't know how it'll all come together. I just know it'll all come together. And so I can just focus on little pieces. I have this thing where I finished one chapter and I think it's really dialed and I love it. And then I start back at the beginning on the next thing and I'm like, wow, this is so bad and not coming together. And I imagine it's like times, you know, 40 when you go from a finished book back to the starting line for the next book. And it's like...

Yeah, because one is done and polished and through many, many rounds of things. One is cumulatively hundreds, thousands of hours of labor. Yeah, thousands of hours of labor, I guess. And the other is like one hour. A vague idea. Yeah. And one has been tested and stress tested and challenged from all these different areas and the other isn't.

And so you have to get more comfortable with crappy first drafts and you have to get more comfortable with crappy first drafts. And you have to get more comfortable with like, in progressness. If that's that should be a word, I think in progressness, like you have to get comfortable with it being in its partial, unformed shape for a long period of time. Like this chapter I'm working on now, just dumping all the stuff that's gonna be in it, and then just having this huge unwieldy document,

and then just every day making it slightly less unwieldy. Like that Michelangelo thing about you have the block and you're just like getting rid of the stuff. Like I know that I'm just every day, I just have to like put a few disparate things together. And I even think at this point, I've started to get to a place where I have a sense of like the time.

Like I know I will probably be done with this chapter next Friday. I don't know where that came from. That's just my sense. I just sense it's about seven more days. And you know, I just say it's no. Crossed off all the other stuff, done all the other low hanging fruit.

I think seven uninterrupted days should probably get me where I need to go. Was there anything when you went back through obstacle on this pass and you're like, oh, I forgot I did that. I should bring that back to my, or anything you noticed where like- I mean, it was much more like even reading the audiobook. So I wrote it, I've published it, I've read it,

I've talked about it for 10 years, then I rewrote it, or like rewrote chunks of it, edited it, went through copy editing, went through production design on it, and then I read the book and I was like, this is fucking horrible. What is this? You know, like there was stuff that like, I, I had notes on almost every page. Yeah.

So I feel like there's an interesting thing where like, it gets harder and harder to like, as much as, as you read, it has to get harder and harder to be like, surprised or excited about an idea. But like, stuff that was in the last book that you thought, this is not as interesting to me as it once was could potentially be a revelation to somebody who hasn't. Yeah, that's true. Yeah, I'm more like this is more like nitpicky shit. Like, how could I say the word uncertainty four times on the same page? How have I not noticed that?

It wasn't like wholesale stuff. It was more like that is a really clunky phrase But I have touched this like so many times and I'm just noticed and these weren't like I introduced it Recently and now I'm at it. It's like I have touched this Hundreds of times people have millions of I have touched this hundreds of times. People have, millions of people have read this and it never came up that this clunky. So part of it is, I think you just have too high, you have very high standards

and they're only bothering me because you've refined it to a level where that's standing out. But at the same time, yes, I did. It was hard to edit a thing that you know works and not overdo it. Right. And not also be judgmental. Like if it works for someone, it works.

Who am I to say that's not good writing, even though I wouldn't do it that way again. Right. So it's like the spirit of the material is all the same, but it's like, how can I improve it? Yeah. But also respecting the spirit of it, because there's a part of but it's like, how can I improve it? Yeah, but also respecting the spirit of it, because there's a part of you that would,

I wouldn't mind rewriting literally every word, you know? So there's a tension. Yeah, any lessons of going through it that you are taking into the next projects? So I've had the experience now a couple of times. So I think two versions of the ops, or two versions of Trust Me I'm Lying, I think this is my, you know, I'm getting this 10 year apart on, on The Obstacles Away.

And then I've obviously reread stuff that I've written even further ago than that. And the mortification that you feel when you reread your old stuff, you usually feel the most mortified when you read something that expresses intense certainty, extreme judgment, or like black and whiteness. So those things can feel good when you're writing them

and they may even resonate in the moment, but they don't age as well. Because ideally as you get older, you're more considerate. You've experienced more, you understand nuance more, you're more informed. So I have noticed like even in obstacle ego stillness, each one is a little bit longer than the one that came before it.

And then now on courage, discipline, justice, wisdom, almost same trajectory. There's one version of that that reflects a lack of discipline, like you're just getting long winded. But I would like to think what it's actually a reflection of is fuller understanding of the complexity of the topic, the complexity of human beings, it's actually more discipline. It's a reflection of a greater discipline

in that you are not allowing yourself to go with first impressions. Or as Mark Shroves talks about in meditation, just getting the gist of it. You're saying, no, no, no, I actually, I had to express this fully. I'm not gonna allow myself shortcuts or I'm not gonna leave anything out.

There's some version of mastery that is about economy for sure, but then there's this other version, I think, where you are capturing the full picture. And that's hard to do being brusque or brash or like, I would like to think that I am getting more thoughtful that's hard to do being brusque or brash or like, I would like to think that I am getting more thoughtful and better at what I'm doing. And so when you read something that you did a long time ago, there should be some of it that where you're like,

that is just insufficient. That is not fair. That's not enough. Like you let yourself off the hook here. And so obviously that's an experience you have when you go back, but instead of doing it retroactively, ideally you wanna do it in the process of doing the next thing,

like anticipating that tendency and counteracting it. That's what I have tried, that's where I tried to grow at least as a writer. How do you think about the tension between doing that, but then also like not sort of being flip floppy. And like, I have this thing where I was talking to somebody recently and throughout the, over the course of the conversation,

he had one point said to me, like you're trying to express the universe. Yeah, yeah. Because I was- You have to pick your topic and I think, and then I guess what I'm much more about overriding and refining and winnowing down or boiling down to its essence

than what can appear to be the same thing which is kind of just like a surface level. Like there's gotta be the there, there, I guess. Yeah. Makes sense. When I get blocked is when I'm like trying to play, I see that there's kind of two ways, like what I'm talking about here,

I see that there's like the opposite is also true. And I can spend a lot of time in my head thinking about like, well, how do I? You can't say everything and you can't please everyone for sure. But when I did Justice, it was maybe like 80,000 words. And then I sat on it for almost a year. And when I picked it back up, I went over it like line by line. And I cut almost 10,000 words out of it. Yeah. And then I added back in like three or 4000

words. So there was this process there of taking a thing which I thought expressed all of it, boiling it down and then beefing it up again, I guess. Yeah. And I felt like that served the book really well. Yeah, you always had like, I don't know which drafted is but you'll send me one day if you had to cut 10% which 10% would it be? I got that from Tim Ferriss. He was like, what would you cut from? He doesn't want you to tell,

Tim doesn't want you to tell him what you like about it. And he doesn't want what you should fix. He wants to know like what is, like where are you lagging? So that's one of the things as I reread the book and I have the publisher printed out in more or less like the shape of what the book will be. Sometimes I even have them like do a bound version. And I, as I'm reading it, when am I myself finding

that I'm skimming, like when am I skimming my own work? And so that feeling of like, oh, okay, I'm done with this. That's somewhere that I understand I have to go back and like tighten. Yeah fix Yeah, so you're boring yourself. I mean Another good thing I got from you was like when you're asking somebody for feedback on a writing project is like Here's what I'm trying to accomplish and it'd be helpful if you look out for where I'm not doing that Rather than just being hey, can you give me some thoughts on this? Well, I learned that on the obstacles away.

So in my mind, I'm not in the obstacles away. It's a book about all these other people. And I don't remember putting a single I or me in the book. And I remember cutting very vividly some things from the, when I came to that conclusion, I like cut it. And then I cut all the instances of it. And then I remember I was, someone asked me to read a passage,

like a book signing or something. And there's like, I flipped it over and like, it's like, there's an I in the middle of the book. And I take a picture of it and I email my editor, I was like, hey, somehow an I like slipped in here, you know? We gotta cut this. And she's like, well, it would have been nice if, she was like, it would have been nice if you told me that that's what we were doing. Like, she was like,

I was never aware that was a rule. Right. And I was like, oh, that's great advice. Okay, I'll do that going forward. Like, hey, this one, but then imagine my frustration that as I was reading the audiobook, this time for the updated edition, I found another one. Like how I like thought I was reading the audio book this time for the updated edition, I found another one. Like how? I like thought I was doing that as I was writing it the first time. I have edited going forward. It's been through multiple rounds of revisions now

and it's still there. So yeah, sometimes you just can't see what you've been looking at very closely. And so communicating that, hey, this is like the style guide or this is the approach that can be really helpful. Yeah, well, cause it also can happen is like, if you just send them a that, hey, this is like the style guide or this is the approach that can be really helpful. Yeah. Well, because it also can happen is like if you just send them a document, say, hey, can I get some thoughts on it? And they give you a bunch of feedback that's like... Not getting you further or closer from where you want to go.

Or it's just like, I precisely am like not doing that. Yes. Yes. And so just getting on the same page about this is what I'm trying to accomplish. How do you determine, like I was listening to your episode with Rich Roll recently, and he was like, my favorite thing in this book, in the Justice book, was the afterword where you do insert yourself into it. And I remember listening to you a long time ago on,

who's the guy that wrote Essentialism? Oh, what is it? Greg McCallan. Yes. And he sort of went out of his way to, I forget which book it was, but you did a similar thing where it was a story about you. Yeah.

And so how have you determined to start to insert yourself? I think there's a difference between making the book about you and then talking about it at the end. I just want, I just don't want to be a main character in the book. I don't know if just don't want to be a main character in the book. I don't know if it's an imposter syndrome thing or whatever, but like, I would like to talk about like really great, fascinating, intriguing, well-known people.

I dislike it when I'm reading a book and the person's like just telling me some boring ass story from their life. You know, I'm like, who are you? I usually see that as an indication of insufficient research or sort of historical grounding or ego or whatever. So that I was never gonna be in the virtue books, but then I did realize, okay, if you're talking about virtue

and you're making strong judgments, positive and negative of other people. There can be an implication that you're somehow the master of these things. So I went through a similar thing on ego is the enemy. There's a preface to ego is the enemy that I'm in for that reason. I just don't wanna come off as holier than thou.

So I want, in the afterwards and in that preface, I'm trying to hold myself to the standard that I am or subject myself to the scrutiny that I'm subjecting the characters in the book to. But I feel like it's separate than the book. You only need that if you're looking to know a little bit more about who made the thing, but it's not essential for your understanding of the ideas in the thing, if that makes sense. So like, even in this, like you could skip the new author's note and just go to the book as it's always been and all the, you know, the book is the book, but if you wanna know

a little bit more about the context in which it was made and who made it and some of the lessons I have learned in making it, that's there. But I see it as additive as opposed to like essential. Right, and when you're writing about yourself, it's usually like, it's the worst in books when it's like, I was talking to a client, I gave him this great advice

and it's like kind of weird sort of subtle brag. It's this this weird humble brag and you don't even know if it's true, you know, like sure what's their experience of what you're saying, you know? So yeah, when I'm, when I, I would say that my, in certainly encourage good amount in, in discipline, definitely injustice. I haven't written it for wisdom yet, but I'm talking about my struggle with that virtue, as opposed to my mastery of that virtue. And my feeling was, if I didn't do that, the implication is that the book is from the expression of my mastery of it, which I do not have.

Yeah. So presenting yourself as sort of a fellow traveler of I'm someone who needs this as much as anyone. Yeah. And that's where this is coming from. Yeah. Cool. Well, thanks, man. Yeah. Thank you. 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 would really help the show. We appreciate it and I'll see you next episode. If you like The Daily Stoic and thanks for listening, you can listen early and ad free right now by joining Wondery Plus in the Wondery app or on Apple podcasts. Prime members can listen ad free on Amazon Music. And before you go, would you tell us about yourself by filling out a short survey on Wondery.com slash survey.