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The Daily Stoic

9 Oct 2024 · 1h 8m

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

In short

The Daily Stoic podcast, hosted by Ryan Holiday, features daily meditations inspired by Stoic philosophy and conversations with various guests discussing the application of Stoicism in modern life. In this episode, Ryan reflects on the 10th anniversary of his book, The Obstacle Is the Way, and shares insights on the evolution of his thoughts and writing style over the past decade.

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1:07Welcome 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.

1:52hey 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 i 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'm in better shape. 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.

2:41And while I was there, I emailed my agent. 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 Obstacle is 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 Obstacle is 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 the first time I'd ever given a public talk.

3:13And 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 Away was sold and then came out, 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 dailystoic.com slash obstacle. We sold out of them when we did this for Daily Dad, and we sold out for Right Thing Right Now and I think Discipline is Destiny.

3:56So those will definitely sell out soon. Grab those at dailystoic.com slash obstacle. but um i was in the office on friday and billy oppenheimer my researcher and uh 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 audiobook 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.

4:28And 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 going to 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.

4:58I 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 of 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 going to be doing a talk in Brazil anytime soon, but if you want to come see me in Europe, I'll be in Rotterdam, London, Dublin, Toronto, and Vancouver.

5:41And 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 going to do a bunch of Q &As as part of those talks as well. So I hope to see you there.

6:08All 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. 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, 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.

6:47And so I was reading it and I was struck by just like how different it was from how I feel like I write now. Like there was, no, that's bad in any ways. I was obviously very proud of the book, but there was just things that I wouldn't let myself get away with now. Like 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.

7:28The central point still stands, but I would rewrite it if I could. 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? And 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?

8:00So there's a bunch of stuff swirling around about why or that it would be nice to get another crack at it. And on all my books, I keep researching even after I stop writing. And so I had also just a big stack of note cards of 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, in other cases, not aged well. And I did this on Trust Me, I'm Lying also, but I think it was like a five-year anniversary edition because stuff in the media changes faster than this.

8:48But I don't know. I really wanted to just make it better. And I wanted to also reflect who I was writing the book at 25 is very different than who I was rewriting it at 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 audiobook of The Obstacles Away and barely recognize the voice of yourself, that is a surreal kind of mindfuck of an experience. Like doing an audiobook is already a strange feeling.

9:35I learned that when I was doing the audiobook for The Obstacles Away. The way you hear your voice is it rattling around through your skull, I guess, when it comes out of your mouth. And then when you listen to it on headphones, when you listen to it recorded, it sounds very different. And so doing an audiobook or a podcast is already strange because you're like, oh, that's how I sound. But to listen to an audiobook 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.

10:17That 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 obstacle is the way. I think in my early 20s, 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, what is it before a preface?

10:54The reflections. Yeah, yeah, yeah. And what you sort of left off that phrase. 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 obstacle is the way 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.

11:37When 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 Mark Surrelius 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.

12:20In Seneca's case, it's a chance to sort of toughen himself up. In Epictetus' case, it's this 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 want to change and what stays? There's a bunch of very specific things that I had notes that I wanted to change.

12:58And 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 audio book, which I just did in this chair, having to say every word of it out loud was like 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.

13:49And 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? 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 Away 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.

14:34And I definitely don't want to be true. I mean, what was, what was the point of continuing to do it if you're not getting any better? I always think you have a, 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 don't step 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.

15:08And yeah, the meaning of it can be different. So yeah, like when I talked about Rockefeller at 24, before 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.

15:52Those 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.

16:38And so I just, yeah, I have these like, it's like comedians talk about tags, which is like a thing at the end of a joke. There's just a lot of little tags or 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.

17:15And 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.

18:01I'm now obligated and able to give a fuller picture of the philosophy that I think is more urgently needed than it was then, if that makes sense. Yes. Yeah.

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19:45That's human with two N's dot com slash stoic for an extra 15 % off with code stoic at checkout. We just took our kids to an outdoor performance, 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.

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21:03Becky. 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.

21:23You 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 what 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.

22:03And 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 is the 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 it getting a surprising amount of media attention compared to what people thought it would get because it was so unusual and weird.

22:41And 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 for 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 than either they were playing their cards very close to the vest or somebody screwed up.

23:51I 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 too that they thought their prediction for The Obstacles Away was that it would sell like 5 ,000 copies. And I thought this person was my friend. So that's not a very nice thing to say. But I didn't think it would sell that few, but I wouldn't have said it would sell 100x that. You know, I didn't think that. I don't even think I thought 50x that. I wasn't thinking it would be a home run. I thought it would be a solid single.

24:28And 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 Obstacle's Way is that there's just not enough female stories in it. That's a criticism I got from many people over the years, and they were totally right. I just didn't have that many. 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.

25:09And I think Margaret Thatcher's in there. There's a couple other examples, but 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. That's true. But I wouldn't let myself out the hook that way. There just wasn't, I just didn't, I 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 I, whenever I give talks, I try to draw something from their world that will illustrate the ideas.

25:43And 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. Two, 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.

26:15And 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? Like, do new album covers, add some new songs, and like, 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 Ares tour is, the biggest tour of all time, even the movie about it's made like a couple hundred million dollars.

26:52That'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. uh 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 catalog worth millions of dollars you know from the other company that owns it and you somehow figure out a way to let that make you the underdog is and and that like people should be rooting and cheering for you.

27:42It'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 haven't heard of. 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.

28:19When I 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 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 did you put this Obama story in there?

29:00And 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 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.

29:38So 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 Greene. So I would say I was also more amoral in, not immoral, this is the distinction Robert Greene makes, but Robert Greene says, you know, there's a difference between an amoral story and an immoral story.

30:25An immoral story says, here's this fucked up, awful thing. You should do this. And an amoral says, here's something that happened. You should understand it. And I would say that the first draft and then ultimately what 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 want to talk about anything you cut? Well, I mean, I can't hide it.

31:03It 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 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.

31:44Right. And so I think that's an important lesson when you study history. There are no perfect characters. Not even Marcus Rillies or the Stoics are perfect. So your understanding of the people, you get more and more layers to them. But that was 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. I think it's, again, you go back and 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 uh you know we talked about this last time christy noem uh how 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 her 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 this story?

32:41And it's not like I was glorifying his abhorrent political beliefs or his associations with Nazism. 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 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 with 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?

33:27Have you thought about how this is going to age? Have you thought about how this might be heard or felt by a audience different than you. So yeah, I've like, it's not like, I wouldn't say I regret including it, but like, clearly I'm not including it anymore. So it 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, it would have been delusional. I joked about this when I gave my talks in Australia earlier this summer.

34:04I was like, if I had predicted any of this for The Obstacles Away, I shouldn't have been allowed to write Ego as the Enemy. So for me to go, hey, how is this going to 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. you learn. Do you think now the, the awareness that there is that large audience, how do you think about like not letting that get into your, your process? Oh, that's interesting. Yeah. Uh, yeah. You want to be cognizant that the audience exists, but you can't be paralyzed that the audience exists.

34:46And there's kind of attention to that. I think I 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 Way, 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.

35:24You 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 an appointment with the president. And the bane of his existence or the bane of his advisor's existence was that 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 are the two presidents assassinated? Garfield and who was the other one? I don't think it was Garfield.

36:01Maybe it was. He's assassinated by a job seeker who gets rejected. Like he meets and 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 it puffs you up.

36:38But 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 from a reader that got a lot out of the book and applied it in a way that you thought?

37:19Well, 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 had gotten connected by someone and he said, oh, I've read your book, The Obstacles Away. And I said, oh, that's insane. How did you hear about it? And he told me that some Arab king or sheik had given it to him. So 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 head of state or influential leader in the Far East is crazy. 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.

38:15But to me, that's the power of stoicism is that 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's lots 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 yeah no it is so So if Zeno is discovering Stoicism between 400 and 300 BC, and then Marcus Aurelius is discovering it, you know, between 100 and 280, that's hundreds of years.

39:04And that's hundreds of years. It would have been... So Stoicism would have been ancient philosophy to Marcus Aurelius. Right. We think they were like hanging out together, all the ancients. Yes. Yeah, 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. Right. Like old enough that there would have been like fossils of dinosaurs while there were dinosaurs, you know? And so the idea, Mark Stereos in Meditations quotes Euripides, this Athenian playwright, and he quotes a play that was lost. So you go, oh, okay, it was lost.

39:42But 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've 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've 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.

40:26But 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 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. He would have thought he lived in the most cutting edge, futuristic society that had ever existed.

41:06The 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 kept them on these little papyrus rolls. Actually, I just read this book called Papyrus, which is incredible.

41:44All these things were preserved in the Library of Alexandria, and there was another library in Pergamum. These were just—that was literature. So he wouldn't have picked it up word of mouth? Because you said it was lost. No, what I'm saying is that play is lost to us today. So we think it's obviously lost since Mark Surreal. I'm sure 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 marcus found it you know like it could have burned in the burning of the library of alexander 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 other the renaissance the enlightenment and then today but that period of classical greece and athens is hundreds of result.

42:30You'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 is like that quote, um, 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 river choice. 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.

43:18You can really only understand that when you have been through one. So imagine somebody reading Mark Surrealist 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, then you read them in 2020 or in 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 who are gone post pandemic but still here yeah you know and i think that's what he's saying do you think the events of the last three, four, five years?

44:19How did that impact people coming to the book? Oh, sure. I mean, the pandemic was obviously a huge inflection point. Like you look, you can look at sales of Marx and Reels' meditations and like, you know, they're sort of flat and then the obstacles away 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 bunch of things, but, uh, the irony is, okay. So you, you're March of 2020 and all of a sudden bookstores are closed, all speaking stops in-person podcasts.

45:04Stop, 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 of the way is introduced to a whole different audience because this terrible thing happened. Now, again, this is one of the, I think, the thing that people miss in the book.

45:43You 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?

46:08Thanks 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.

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48:14I'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?

48:48I 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 sort of took, when he said it, it made me think of, and you have this, this quote in the reflections part, the Borgias quote. Oh yeah. And, and just like how those things are like what we ultimately use in, in our work. I get, yeah. So there's a Borgias 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.

49:22But 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 Stoics are saying that everything is this opportunity to practice virtue, obviously obstacles are a particularly salient example of that chance. But success presents certain obstacles too. So Marcus Aurelius is 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.

49:58And it is precisely the privilege and the power and the immensity of it that demands the excellence and is the opportunity, right? Like he can now do whatever he wants and the opportunity is for him to sort of rise to that challenge and go, I'm going to be good despite this abundance and success. And so, like, sure, if the obstacles away had failed and been 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.

50:57Well, 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 it's the idea is that everything is this chance to practice, uh, 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 Superbowl and now everyone has extremely high expectations and the team is coming apart and you have to.

51:42try to repeat. That's also an obstacle. It's a nice obstacle, but it's not easy. And so the idea is that every situation, good ones, bad ones, big ones, small ones, they're this opportunity to practice. That to me is ultimately what means to say that the obstacle is the way. Yeah. As I was looking into the Wooden stuff for... Yeah, the George Rattling book. Wooden had this line about he wishes all of his best friends would win one championship and all as enemies were going multiple. Yeah, because it's destabilizing and overwhelming and can bring out the worst in you. I mean, more often than not, do people wear success well?

52:23You know, 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 bestseller list, for maintaining any level of excellence or dominance in a given field.

53:15Or, 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. problems and how much money. But it's like a real thing. So what do - Well, look, you did it. You sold a book, right? People don't know Billy sold his first book and he's working on it. That's wonderful, exciting. 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.

53:55And 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 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.

54:42You're right. The easiest part or the hardest part began after the proposal for sure. Uh, an ego's enemy of this quote from John Wheeler and 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 got to get to here and then you get to hear 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.

55:31Yeah. 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 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, well, 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 going to 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.

56:13You 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, 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, if you think back to when you, you're starting obstacle or ego and what, what did you learn about? Like, that's not something I I'm going to do.

56:49I'm just much more comfortable now on books knowing that I don't know where it's going to end up. Yeah. And at the same time, much more confident that I know it's going to end up, if that makes sense. Yes. 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 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.

57:31And 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 I, 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.

58:27I 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 finish 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 40 when you go from a finished book back to the starting line for the next book.

59:02And 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 yeah and uh 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 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 going to be in it in it and then just having this huge unwieldy document and then just every day making it slightly less unwieldy.

1:00:00Like 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. You know, I just said, 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.

1:00:38Was there anything when you went back through obstacle on this, this past and you're like, oh, I forgot how I did that. I should, I should bring that back to my, or anything you noticed? I mean, it was much more like even reading the audio book. 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 audiobook 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.

1:01:21Yeah. So I feel like there's an interesting thing where like, it gets harder and harder to like, as much 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.

1:02:02And 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 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 you 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 yeah 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 and and but also respecting the spirit of it because it there's a part of you that would like i wouldn't mind rewriting literally every word you know uh so there's a tension.

1:02:59Yeah. Any lessons of going through it that you are taking into the next projects? So I've, 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, uh, the obstacles away. And then I've obviously reread stuff that I've written even further ago than that. And there, 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 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.

1:03:49Because 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 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.

1:04:31It's a reflection of a greater discipline in that you are not allowing yourself to go with first impressions, or as Mark Schroes talks about in meditation, just getting the gist of it. You're saying, no, no, no, I actually, I have to express this fully. I'm not going to allow myself shortcuts. or I'm not going to 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 and better at what I'm doing.

1:05:16And 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, and so obviously that's an experience you have when you go back, but instead of doing it retroactively, ideally you want to do it in the process of doing the next thing, like anticipating that tendency and counteracting it. That's what I have. That's where I've 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.

1:05:54And like, I have this thing where I was talking to somebody recently and throughout the, over the course of the conversation, he had, he had one point said to me, like, you're trying to express the universe because I was. So pick your topic. And I think, and then I guess what I'm, 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 got to be the there, there, I guess. Yeah. When I get blocked is when I'm like trying to play. I'm trying, I see that there's, there's kind of two ways, like what I'm talking about here.

1:06:34I 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, uh, 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. And then I added back in like three or 4 ,000 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. And I felt like that served the book really well.

1:07:19Yeah. You always have like, I don't know which draft it 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, what is like, where do you like? So that's one of the things as I reread the book and I, I have the publisher printed out in more or less like the shape of what the book will be. And 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 like, when am I skimming my own work?

1:07:58And so that, 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 and 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 be like, hey, can you give me some thoughts on this? Well, I learned that on The Obstacles Way. So in my mind, I'm not in the obstacles away. It's a book about all these other people.

1:08:38And 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 flip it over and I'm 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 eye slipped in here. We got to cut this. And she was 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.

1:09:11Like, 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 is what I'm doing. But then imagine my frustration that as 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, so yeah, sometimes you just, 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.

1:09:50Yeah. Well, cause it also can happen is like, if you just send them a document and 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 and the justice book was the afterward where you do insert yourself into it. Sure. And I remember listening to you a long time ago on, who's the guy that wrote Essentialism?

1:10:26Oh, Greg McAllen. 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 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, I dislike it when I'm reading a book and the person's like, just telling me some boring ass story from their life.

1:11:05You know, I'm like, who are you? Uh, I, I usually see that as an indication of insufficient research or sort of historical grounding or ego or whatever. So, so that I was never going to 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 want to come off as holier than now. So 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.

1:11:58But 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. 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, the book is the book. But if you want to 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.

1:12:36Right. 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 a weird sort of subtle brag, but. It's this weird, humble brag. And you don't even know if it's true. Right. 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, in, certainly encourage good amount in, in discipline, definitely in justice. 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.

1:13:13And 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 it would really help the show we appreciate it and i'll see you next episode

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From the publisher

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


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