Turning Adversity To Advantage: Ryan Holiday on Why The Obstacle Is The Way

I love talking to smart people. Today's guest is certainly that — and so much more. Contravening millennial stereotypes, Ryan Holiday is a prolific, rising literary talent. A maverick media strategist. Not to mention a philosopher of sorts — a guy with big ideas often at odds with the status quo. An autodidact, Ryan dropped out of college at nineteen to apprentice under acclaimed author Robert Greene, author of (among many other great books) The 48 Laws of Power*, later graduating to advise many New York Times bestselling authors like Tim Ferriss and RRP #154 alum Tucker Max, multiplatinum musicians like Linkin Park and startups like Casey Neistat's ( RRP 73 & RRP 144 ) recently launched social media platform Beme. By the time he was legally allowed to drink (21!) Ryan had already ascended to director of marketing duties at American Apparel, where his iconoclastic campaigns and tactics have been used as case studies by Twitter, YouTube, and Google and written about in places like AdAge, the New York Times, and Fast Company. Ryan is also the bestselling author of 3 books, including Trust Me I’m Lying* – a highly entertaining and admittedly disturbing first hand look at the machinations behind digital media's dark underbelly — and The Obstacle Is The Way* – a modern and practical reframing of stoicism, the ancient Roman philosophy originated by guys like Marcus Aurelius, Seneca and Epictetus, with a focus on functional applicability of stoic principles for turning modern day obstacles into opportunities and adversity to advantage. If you think philosophy is purely academic — a useless waste of time reserved for the arrogant intellectual elite — Ryan has a message for you: think again. I really love this book. I found it to be eminently practical. An incredibly insightful and utilitarian tool box for navigating crises, strengthening character and maximizing excellence in any situation, irrespective of circumstance. On RyanHoliday.net and places like Thought Catalog and Observer (where he is editor at large), Ryan writes frequently on a wide variety of business and marketing related subject matters. But it's his fresh and unique take on real life stuff that keeps me coming back. Enjoy! Rich Learn more about your ad choices. Visit podcastchoices.com/adchoices

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Rich Roll?

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• 1:04Ryan Holiday?

  Yeah, it's interesting. I think with the light, I think at the root of a lot of these life hacks is the idea that people really don't like uncertainty. And creative endeavors are inherently uncertain. And so they're always looking for some sort of shortcut, or some sort of, some person that says, if you do X, Y, and Z, you will get this thing. And that's just not how it works.

• 1:24Rich Roll?

  That's Ryan Holiday, and this is the Rich Roll Podcast.

• 1:39Ryan Holiday?

  The Rich Roll Podcast.

• 1:42Rich Roll?

  Hey, everybody. What's the news? What's going on? The podcast is going on. That's what's happening. My name is Rich Roll. I am your host. And this is the podcast where... I sit down with the outliers, the paradigm breakers, the big forward thinkers, the out of the box minds and personalities across all categories of excellence and positive culture change to mine the tools, the insights and the principles that can help all of us unlock and unleash our best, most authentic selves. So, thank you so much for tuning in today. Thanks for subscribing to the show on iTunes and thank you for subscribing to my weekly newsletter. If you want to support the show, there are two great free ways to do it.

• 2:25Rich Roll?

  The first way is just take a quick moment and give us a review on iTunes. It'll only take you a second and it really does help us out tremendously. Second, next time you're about to buy something on Amazon, first click through the Amazon banner ad at richroll.com. It will not cost you one penny extra on your purchases and it's just a really easy, great, free way to support the mission. And you can make it super simple by just bookmarking the link from the banner ad on my site to your browser. That way you don't have to keep coming back to my site and it's easy. It's a win-win across the board. Okay, so this week I got Ryan Holiday on the show.

• 3:05Rich Roll?

  Prolific literary talent, maverick guerrilla marketing iconoclast and media strategist. And generally, Ryan is just a really cool, young, incredibly well-read guy with some really interesting and compelling ideas on a wide array of topics. And I've been a big fan of Ryan for a long time. I've been reading his stuff forever, so it's super cool to have him on the show today. A little bit more about Ryan and his background in a minute, but first...

• 3:41Rich Roll?

  All right, Ryan Holiday. So, Ryan is an extremely bright young man. He's very savvy. I think it's fair to characterize him as an out of the box thinker. Again, he's a media strategist and he's a prominent and rather prolific writer on a wide variety of subjects, not the least of which are strategy and business. He's also an autodidact, which means he's predominantly self-taught because he dropped out of college at 19 when he had the opportunity to apprentice under the famous author, Robert Greene, who wrote an amazing book called The 48 Laws of Power, among many other books. And then Ryan went on to advise... A number of bestselling, at times controversial, authors on their book launches.

• 4:24Rich Roll?

  Guys like Tim Ferriss and Tucker Max, who's a former guest on this show, as well as multi-platinum musicians like Linkin Park. He also served as Director of Marketing at American Apparel for many years. He tells a lot of amazing stories about that experience in his book, Trust Me, I'm Lying, where his unique and maverick campaigns and tactics have been used as case studies by Twitter, YouTube, and Google, and written about all over the place, in places like Ad Age, The New York Times, and Fast Company. He's also the bestselling author of three books, including, again, Trust Me, I'm Lying, which is a very entertaining, at times disturbing firsthand look at how, how do I characterize

• 5:04Rich Roll?

  this, the dark underbelly of the modern media machine actually functions, and how it actually can be leveraged, or to use his words, manipulated to work in your favor. And also, his newest book, The Obstacle is the Way, which is a modern, I guess you could call it utilitarian reframing of the ancient Roman philosophy of Stoicism, which was a philosophy pioneered by guys like Marcus Aurelius, Seneca, and Epictetus. And essentially, it's kind of a primer on the functional applicability of Stoicism for navigating today's world, including formula for turning obstacles into opportunities and adversity to advantage.

• 5:48Rich Roll?

  And I really love this book. I found it to be incredibly insightful and helpful, and really, it's a practical roadmap for maximizing excellence in any situation, irrespective of circumstance. And the principles behind this book really form the basis for much of our conversation today. Ryan also writes and blogs frequently on, again, a wide variety of subjects, and like real-life stuff. He does this on his website, ryanholiday.net, and on places like Thought Catalog and The Observer, where he is editor-at-large. Ryan is a voracious reader, so I highly suggest that everyone subscribe to his monthly reading recommendation newsletter of books that he's read, reviewed, and thinks you'll like.

• 6:33Rich Roll?

  It's really great. You can do that at ryanholiday.net. So. I love talking to smart people and Ryan is certainly that and more. This is a really interesting conversation about many, many things, not the least of which include how we misperceive struggle, how it's actually a defining characteristic of success. In other words, the gift of obstacles. It's about how the principles of Stoicism can help eradicate the barriers that hold us back. We talk about reconciling the principles of Stoicism with populist notions of life hacking and we get into a really interesting dialogue about how modern marketing actually works in our clickbait, schadenfreude, internet shaming culture.

• 7:15Rich Roll?

  And also kind of how to discern the internet snake oil salesman from the valuable content that's available to us online. So, all right, let's tap this brain, shall we? Ryan Holiday.

• 7:35Rich Roll?

  Thanks for coming out to the hinterlands to do the podcast. I appreciate it. Yeah, of course. Anytime to come to the hills, I would totally do it. Well, next time, we gotta go on a run, man. That's what all I was thinking about when I was driving out. Yeah, look behind you, look at the hill. Actually, you should be sitting where I'm sitting so you could look at the mountain, but maybe that'll be distracting for you. But there's plenty of trails out here where you can get lost. I might go for a run on the beach on the way back. Yeah, that would be good. So what are you doing here in LA? Just some meetings, some client work, and then I'm just doing some podcasts. Uh huh. That's right. You came out just for the podcast, right? Exactly. Awesome, man. Well, I'm honored and I've been a big fan of your work for a long time. Oh, thank you. I love your writing, your books, as well as all the articles that you write.

• 8:18Rich Roll?

  And they're always so insightful and I feel like you're, you know, you're on a different level than a lot of people out there. So it's a pleasure to talk to somebody who... I think grapples with and really thinks deeply about things that are important to me and I think are relevant to culture in general.

• 8:37Ryan Holiday?

  It's weird, like a couple of years ago was like, there was all these people that you felt like you knew because like you read their stuff. And then now with podcasts and then with you specifically, because I've been following you on Beam, not to plug it right out of the gate, but like you feel like you have this insight into, like you feel like you've known these people or you, even though you've never actually met and you don't actually really know anything about them.

• 8:58Rich Roll?

  Right.

• 8:58Ryan Holiday?

  But like you, you like dive right into their life from like the get go and it's very strange.

• 9:04Rich Roll?

  It is strange. It's cool. I mean, I think Beam, you know, to kind of take a tip from, from, you know, Casey's mission statement on that is to, you know, make it more authentic. So you're stripping away all the filters and the editing and all of that. So you are getting kind of a more authentic portrayal of someone's life and all its pimples and, you know.

• 9:22Ryan Holiday?

  Yeah. Or like, because people will be like, oh, like I listened to your audiobook. And then it's like weird because it's like, so you heard me talk for like eight hours directly like inserted into your brain like that, that like makes me uncomfortable.

• 9:35Rich Roll?

  Well, it's, it's very personal, you know, and I can tell you from doing the podcast, I've been doing it for like two and a half years now, that when I, not so much in LA, it doesn't really happen in LA, but when I travel to other places and, and, you know, people will stop me on the street or in the subway and, and they really do feel like they know you. And in certain respects, they do, you know, like, like I have 400 hours of me talking out freely, you know, floating around in the internet. So.

• 9:59Ryan Holiday?

  It was like they were in the passenger.

• 10:01Rich Roll?

  They probably know me more than most people.

• 10:03Ryan Holiday?

  It was like you were in the passenger seat in their car while they drove to work every day for a month.

• 10:08Rich Roll?

  Right. With their earbuds in, it's very personal, you know, and I have that experience from, you know, I've been a fan of podcasting for a while. So I feel like I have that relationship with like Marc Maron, right? Like I've listened to him so much, I feel like I know that guy. And, and you project onto these people, this relationship that is an illusion, you know, you feel like he's your friend.

• 10:27Ryan Holiday?

  Yeah. Like with, with Maron, I think it's weird is like you hear it, like he has these different laughs and like you know, and he really thinks something is funny. It's like this, you're, you're analyzing a person way deeper than you would ever actually, you would even get with your friends.

• 10:41Rich Roll?

  Right.

• 10:41Ryan Holiday?

  It's weird.

• 10:42Rich Roll?

  And I think with him in particular, because he's, he wears his emotions on a sleeve, you know, it's not a canned presentation. Like you're getting who that, who that guy is.

• 10:51Ryan Holiday?

  Totally.

• 10:51Rich Roll?

  And there's something special about that.

• 10:53Ryan Holiday?

  Yeah, I think so.

• 10:54Rich Roll?

  So, anyway, all right.

• 10:55Ryan Holiday?

  All right.

• 10:56Rich Roll?

  I feel like I know you from your writing and I have listened to, you know, two of your audiobooks.

• 11:00Ryan Holiday?

  Awesome.

• 11:01Rich Roll?

  Here we are in person, which is, it's almost like it's just a, um, what's the word? A formality.

• 11:07Ryan Holiday?

  Yeah, yeah, yeah.

• 11:09Rich Roll?

  Oh, hey, Ryan's here.

• 11:10Ryan Holiday?

  Right.

• 11:10Rich Roll?

  You know what I mean?

• 11:11Ryan Holiday?

  Right.

• 11:11Rich Roll?

  So, cool. Well, there's so many inflection points and so many things that we could talk about. Um, you know, I feel like I could do a two-day podcast with you and we could just talk forever. And we actually did a half-hour podcast that was not recorded before we shut it down. Um, so, you know, in terms of trying to focus it a little bit, um, I think a good place to start off with is, is really, um, you know, just talking about your latest book, The Obstacle is the Way, which I absolutely loved and the ideas behind Stoicism, which I find to be highly relevant uh, in my own life, they really resonate with me deeply. Um, and I'm interested in kind of, you know, exploring these ideas, uh, you know, a little bit in depth.

• 11:51Rich Roll?

  So, to kick it off, maybe sort of explain a little bit what Stoicism is for the uninitiated?

• 11:58Ryan Holiday?

  Yeah, so Stoicism is a, is a Roman philosophy, a Greek and Roman philosophy, sort of three most prominent practitioners. Like, I could go into the ethics of it, but I think that sort of misses the point. I like to focus on the people that are sort of identified with it. But sort of most prominent would be Marcus Aurelius, the Emperor of Rome. He's the guy in Gladiator, if you know nothing of Roman history. Um, so you have the most powerful man in the world who, who wanted to be a philosopher, who, who sort of, his father was not the emperor, he was sort of selected for the throne. And so you have this, this weird idea of a philosopher-king, maybe like the only time that ever happens in history. The other prominent Stoic is, is Epictetus, who was a slave, um, who was banished by a different emperor,

• 12:42Ryan Holiday?

  um, and, and actually sort of like physically crippled as a, as a punishment. And, um, so, so you have this philosophy that on the one hand is sort of embodied by like the most powerful man in the world, and then one of the least powerful men in the world. And they're both sort of struggling with these sort of eternal questions of like, you know, what is the meaning of life? How do you deal with a world that you don't control? How do you, how do you, you know, sort of subtracting God out of it? How do you, how do you find purpose? What's, what's right and wrong? How do you live your life? You know, what, what is the? What is the path to the good life? And then practically, how does one actually do this? These are the sort of questions of Stoicism. And it's the most sort of practical, readable, accessible philosophy.

• 13:27Ryan Holiday?

  It's not, you know, how many angels can dance on the head of a pin? It's not, you know, what's, what's the, you know, is all of life a dream? You know, it's not these sort of esoteric-

• 13:39Rich Roll?

  Like a purely academic pursuit.

• 13:41Ryan Holiday?

  It's the 100% opposite of whatever you think philosophy is and whatever you may have experienced in school. It's not that. It's, it's very practical. Like Marcus Aurelius is a guy with an immense burden and immense temptations, sitting down every night and writing little notes to himself about, you know, like what he should do or what he shouldn't do or what he's learned. And then this work survives to us and it's called Stoicism. And that, I was introduced to that, I was like 19 years old, a really smart person was like, hey, you should read this. And I did and it's sort of-

• 14:14Rich Roll?

  Dr. Drew.

• 14:15Ryan Holiday?

  Yeah, yeah. I was at this conference and I was like, hey, like, you know, what book would you recommend to like a young person who's like trying to figure out their life? And he was like, I think you should read the Stoics. And so I, I did. And it just sort of, you know, totally blew my mind. It's Tyler Cowen calls them quake books, like a book that shakes everything you think you know about the world. And that happened to me and it's been this sort of journey ever since. I've probably read the book 500 times.

• 14:41Rich Roll?

  Have you gone back to Dr. Drew and given him a book of, given him the obstacles away?

• 14:46Ryan Holiday?

  Yeah, yeah. So I, I mailed it to him and he didn't say anything. And then somebody I knew told him about it. And I got this crazy email from him and he like, he'd read the book and he told, he loved it. And so it was this like full circle moment for me. It was like, like if honestly, if no one had read the book, but he'd read the book, it would have been like my dream come true. So it was crazy. And I'm like such a huge fan of him, so it's like-

• 15:12Rich Roll?

  Right, right, right, right. So while implicit in it is also this, in terms of like the applicability to life, you know, modern life in particular, there's also kind of an inherent optimism that it's infused with, right?

• 15:25Ryan Holiday?

  Yeah, it's weird, like the, so- If you look at, if you ask the person like, what is, what is the word stoic mean? And then you ask them what the word epicurean means, their, their definitions would be the exact opposite of what those schools of philosophy are actually about. So people think stoicism is about resignation.

• 15:44Rich Roll?

  Aestheticism.

• 15:45Ryan Holiday?

  Yeah, and just like bearing just the blunt of the awfulness of life, which is in fact, not what stoicism is, is at all. And I, I base the obstacle in the way, as this line from Marx's theory, he says, you know, the impediment to action advances action. What stands in the way becomes the way. Basically, what he's saying is like, look, you don't control what happens, but you control how you respond to what happens. And so you might as well respond in a positive way. So to me, that is a much more resilient sort of definition of optimism than simply saying like, um, I'm going to believe that the glass is half full, even though objectively it's not half full. Like, you know, like there's this, it's not about sort of delusional positive thinking. It's about saying, this is what objectively is the case. I'm going to choose to do something about it.

• 16:30Ryan Holiday?

  I think that's a better.

• 16:31Rich Roll?

  Well, really at its core, it's about mastering perception, right? And it's about overcoming default, you know, default perceptions of the world and, you know, events that occur to us.

• 16:43Ryan Holiday?

  Yeah, I mean, the first thing that most people do when something happens is they decide whether they like it or not, whether it's fair or not, whether it's reasonable or not, all these things that the Stoics would say have no actual bearing on the event itself.

• 16:56Rich Roll?

  Well, we're hardwired to make, you know, immediate judgments on everything that occurs, right? And I don't know whether we have this sort of dualistic mind that sort of just naturally gravitates towards that, but, but, you know, we're so quick to label something as bad or good or tragic or awesome. And the truth is, is that we lack, you know, even the most, you know, de minimis amount of evidence to make those judgments when they occur.

• 17:21Ryan Holiday?

  Yes, and what I always say is like, look, this thing that you think is so bad, there are, what, a billion, two billion people on this planet who would trade everything to experience whatever that bad thing that you're experiencing is. You know what I mean?

• 17:34Rich Roll?

  But that refrain, you know, doesn't necessarily, you know, salve the wound, you know, like, because you can hear, somebody will tell you that when you're in the midst of feeling sorry for yourself or whatever, and you're like, yeah, yeah, yeah, please go away.

• 17:47Ryan Holiday?

  Sure, but, right, but I think it's about, it's about seeing this thing with a bit of objectivity, and then it's not to say that like, it's not gonna make, it's suddenly gonna make you not sad, but perhaps it'll make you not sad for six months, right? It's about, like, like I say, like, okay, if you get in a car accident, your body's gonna have an emotional response, it's gonna have a hormonal response, you're gonna get that adrenaline dump, you're gonna be scared, you might go into shock. All of this is great. You don't, you don't, you can't, or not great, but you don't choose, you can't change that. But what you can choose is how you respond generally to that accident, right? You can decide whether, you know, you're gonna be scared of driving anymore,

• 18:30Ryan Holiday?

  whether you're never gonna get back in a car, whether you're gonna, you know, you decide the sort of the larger response, not necessarily the immediate reaction. If, if that painting fell off the wall, it's gonna catch you by surprise, but you choose what you're gonna do about it after that.

• 18:47Rich Roll?

  Yeah, I think an analog, and the way I kind of came into these principles was, was not through, you know, meditations by Marcus Aurelius, although I would have benefited from reading that. I probably did read it in college, I don't remember.

• 19:00Ryan Holiday?

  Probably not. College professors hate it because there's not a lot of room for interpretation. Like, he just says what he means.

• 19:05Rich Roll?

  Right, yeah, yeah, yeah, yeah. What kind of paper, what kind of modern spin are you gonna put on that? Well, you were able to do that.

• 19:12Ryan Holiday?

  A little bit, but I just took, I took what they said, and then I just found stories from history and I matched the two together.

• 19:18Rich Roll?

  Mm-hmm. I learned these ideas in a different form through, when I was...

• 19:25Rich Roll?

  When I was in rehab and I came into the Serenity Prayer.

• 19:29Ryan Holiday?

  Sure.

• 19:29Rich Roll?

  Which is very similar, you know, God granted me the serenity to accept the things I cannot change, the courage to change the things I can, and the wisdom to know the difference, which is a very similar kind of idea.

• 19:38Ryan Holiday?

  Sure.

• 19:39Rich Roll?

  At its core. And I think ultimately what it's about is shifting perspective and embracing, sort of distancing yourself from results and embracing process.

• 19:54Ryan Holiday?

  Yeah, yeah, and look, there's a bunch of connections between Stoicism and the sort of 12-step communities. There's a bunch of connections between Stoicism and cognitive behavioral therapy. It's this idea of like, like, look, there, you know, you, you, you have to first decide whether this thing is in your control or not in your control. And the things that are in your control, they, they require a full amount of your effort and energy and passion and all these things. And the things that are not in your control, like, like, I, I think about it like when I'm writing the book. Like, I have to sit there and go like, I'm writing the absolute best book that I can. This is 100% in my control. And then I'm gonna do, I'm gonna kill myself to market it to get in front of as many people as possible. But ultimately, I don't control whether there's a hurricane the day that it comes out.

• 20:39Ryan Holiday?

  I don't control whether the New York Times list screws me over and decides not to include it. I don't control whether people like it or not. I don't control whether I'm ahead of my time or behind my times. Like, I don't control any of those things. All I control is the product. And, and if you don't, if that's not enough for you, then what you're essentially saying is, you just spent a year of your life working on something. And the only way you're gonna be happy about it is if something you don't control breaks your way, which is a real crappy recipe for being a happy person.

• 21:10Rich Roll?

  But I feel like our society is structured on that premise.

• 21:13Ryan Holiday?

  Totally, it totally is. And it's why a lot of people are very, very unhappy. And, and it's, it's, again, like, all of this is way easier said than done, right? Like, understanding that intellectually does not change the fact that every day you have to wake up and your instincts and your natural inclinations are to put your happiness on things that are conditional to other people. And so you, you work on it. You try to get better every day.

• 21:44Rich Roll?

  So one thing that's really interesting to me about all of this is, you know, you're talking about like, timing and timeliness, and I think there's something about this message that you're putting out that is resonating with the culture that's allowed your book to kind of, you know, permeate

• 21:57Ryan Holiday?

  Sure.

• 21:58Rich Roll?

  our consciousness. But I'm interested in how you reconcile that with this fascination or obsession that we have with like, the life hack. Like, how can I shortcut my process to get to the result? You know, which I feel like I've written about this before, and I do a lot of, I've been thinking, I do a lot of thinking about this. And I'm, I'm kind of, look, I'm, I'm all for a good idea

• 22:24Ryan Holiday?

  Mm-hmm.

• 22:25Rich Roll?

  that will kind of streamline your life and, and get you closer to where you want to be. But I'm also disturbed by the amount of attention and focus that is placed on, you know, sort of this, um, this idea of, of, of sort of short cutting the work that it takes to

• 22:44Ryan Holiday?

  Yes.

• 22:45Rich Roll?

  get where you want to go. Because my whole life, basically, the value of anything that I've achieved is a result of engaging the process on the deepest level that I can. Like, allowing myself to give myself over completely to something is, that is the value of it. It's not the result of

• 23:02Ryan Holiday?

  Sure.

• 23:03Rich Roll?

  that endeavor. It is the, it is the, the process itself. And so I feel like, in certain respects, your book is, is really a call to action to, you know, really embrace that ideal. But also, you're a guy who writes on Lifehacker, and, and you're part of the cabal of, like, you know, sort of Lifehacker writers. And so how do you, how do you kind of reconcile those two notions?

• 23:24Ryan Holiday?

  Yeah, it's interesting. I think with the life, I think at the root of a lot of these life hacks is the idea that people really don't like uncertainty. And creative endeavors are inherently uncertain. And so they're always looking for some sort of shortcut, or some sort of, some person that says, if you do X, Y, and Z, you will get this thing. And that's just not how it works. Like, you even see this, like, with, with 10,000, like the 10,000 hours theory. Like, people are like, oh, so it's just 10,000 hours? Like, if I just put in 10,000 hours? Like, you're telling me, like, you're promising me that if I put in 10,000 hours, like, I'm set. And it, it doesn't work that way. When I think about, like, life hacks or tricks, I'm thinking about, and I think, Tim Ferriss is a friend of mine and a client of mine, and someone who's been very good to me over the years. I even think with Tim, like, people are like,

• 24:10Ryan Holiday?

  Oh, Tim only works like four hours a week. It's like, no, Tim does four hours of bullshit work every week because that's the minimum or that's the minimum that he felt he could get away with. So then he could spend the rest of his time doing the actual work that he actually likes.

• 24:25Rich Roll?

  Right. And I think that that gets lost in the discussion. You know what I mean? I think that that was Tim's intention from the beginning. He's like, get rid of all the stuff that's not moving you forward. So you can invest yourself completely in, you know, what gets you out of bed in the morning and gets you excited about your life. But I feel like that aspect of the conversation sort of gets shoved aside and it's, it's all focused on this 80 20 rule or, or, you know, how can I, how can I, you know, complete a marathon with the least amount of training possible, which is sort of like, to me, like, that defeats the purpose of the endeavor altogether.

• 24:55Ryan Holiday?

  Yeah, totally. Like I think, like, exercise is a good example, uh, where it's like, I don't, I don't, I, exercise is my favorite part of the day. I'm not trying to like, get it in as little amount of time. I'm like, I'm, I'm doing these other things I don't like, and then this is my hour and a half to do it. My, like, there's more than just physical benefits to exercise and it's not about shortening them. And, and it's like, like I, I see this with, uh, cause I read a lot and I'm, I'm somewhat known for like my book recommendations and stuff. And so people are like, oh, you must be like a speed reader, right? And I'm like, no, like, I love reading. Why would I try to do it as quickly as possible? Like this is what, this is, this is the thing. Like no one's

• 25:38Ryan Holiday?

  like, no one's ever, think about it this way. No one's like, um, do you have any tips for like, uh, having sex faster? Like, I don't want to like, I don't want it to take so long. Like, in fact, they're like, how can it take as long as possible, right? Like, and yet with like work, which I think is a pleasure, and I think with, um, relationships, which are a pleasure, and with reading, which is a pleasure, it's not about shortening them. It's, it's in fact about eliminating all the extraneous unnecessary parts. So you can fully enjoy it and you can actually engage in it. And I think, I think a lot of people miss the point on that. Like I, a hack for me is like, oh, hey, if you uninstall all these things from your phone, you're going to be less distracted. That's a life hack. Not, hey, if you use

• 26:19Ryan Holiday?

  And Scrivner and this other thing and this other thing. You can you can have a magical way of organizing all your information that like. Means you don't have to think about it like that. That's not the point.

• 26:33Rich Roll?

  Right, right, right. Yeah. So why do you think that that that gets lost?

• 26:38Ryan Holiday?

  Well, because it's a lot easier to talk about working than it is to work. Right? So like, I think like I would say that anytime I've written about like creativity or like productivity. I'm usually doing it probably because like I'm I'm struggling with the actual project I'm supposed to be working on.

• 26:54Rich Roll?

  Right.

• 26:55Ryan Holiday?

  And this is like a way to get maybe a little bit of momentum going. But yeah, I think people people are looking. People, the idea that like you have to do your work and then at a certain point, it kind of leaves your hands. Is such a terrifying idea to someone, someone who's dropped out of college or someone who's quit their job. Or someone who has a kid on the way like. All they want is for someone to say like, like, look.

• 27:22Rich Roll?

  If you do this thing, it'll be okay.

• 27:24Ryan Holiday?

  Yeah, and that's just not.

• 27:25Rich Roll?

  Well, behind that is just is fear, right? So the real work should really be looking at how you're how you're dealing with that fear.

• 27:32Ryan Holiday?

  Yeah, yeah, of course. And the Stoics talk about this. They're like, look, like you could die tomorrow. Let that order how you live your life. And and so I think I think one of the ideas is is to think like I I've I've had to do this like. If if the the thing is not intrinsically valuable or intrinsically sort of pleasurable. It's probably not a good use of my time. Like, so it's like if I'm writing the book only because I think I might make a lot of money from it. Then.

• 28:04Rich Roll?

  That's a flawed premise.

• 28:05Ryan Holiday?

  That's a flawed premise and it's it might work out my way, but there's a huge can it's it's a huge contingency. Dependent on something I don't control that might make me unhappy. And so I I. I think one of the hardest things in the world for people to do is to turn down money. It's obviously a first world hard thing to do, but it's a hard thing to do. And like a lot, I think a lot of the test comes from like. At least for me, it's like this person wants to pay me to work on this project. I don't like that project. Am I gonna be able to say no so I can do what I actually care about?

• 28:35Rich Roll?

  Right, that's the that's the litmus test of like, living your authentic life.

• 28:39Ryan Holiday?

  Totally, totally.

• 28:40Rich Roll?

  And that that's perhaps the hardest thing to do.

• 28:43Ryan Holiday?

  Yeah, especially the more like, because at the end of the day, you're selling pieces of your life to other people for money, right? And so if you don't know what you're getting money for, and more importantly, you you don't know how much you sell your time for. It sets a really bad, uncertain situation where you're just like, oh, that, especially if you get paid well, you're like, well, of course. And this is how people end up being lawyers, working 100-hour weeks, doing stuff they hate, or, you know, this is how people end up signing on to projects that make them miserable. And it's because they don't want to think about those things.

• 29:18Rich Roll?

  Right, and I've I've lived that life, you know what I mean? Like, I I've been on both sides of this coin, so I feel like I can speak to it, you know, uniquely, because I didn't, you know, I didn't get to a point where the pain was sufficient enough to, you know, make the appropriate changes to live the life that I wanted to live until I was like 40 years old, you know? I'm like, old enough to be your dad. And and so I I know what it's like to walk a mile in the shoes of somebody who who is doing something that they don't like, but is being compensated for it. And is so miserable that you you you try to deal with that by, you know, purchasing things that are out of your budget range and then, you know, basically shackling yourself to this to this life that you you feel like you didn't even consciously sign up for to begin with.

• 30:03Ryan Holiday?

  Well, I think for you, so you had that moment, from what I've heard and read, is that you had that moment, you're walking up the stairs, and you have to stop to like, catch your breath.

• 30:12Rich Roll?

  Those stairs right there.

• 30:12Ryan Holiday?

  Oh, really? Yeah, and you're like, and then, uh, most, I would say, most people would have that realization, it would make them feel crappy.

• 30:23Ryan Holiday?

  And that they would go back to doing exactly the same thing that they were doing before. And I think that's the, that's the sort of inflection point. Like, I see this all the time. Like, people are like, "Oh, like, you know, I'm struggling with this." They'll ask for me, ask me for my advice. I'll give them my advice, and I'll talk to them like two months later, and they'll have the same problem. And I'm like, "Oh, the advice didn't work?" It's like, "No, they just didn't actually do it."

• 30:43Rich Roll?

  They didn't read the book that you recommended. They didn't take the advice. And, you know, this is the plight of being human, I think. And, you know, I spent a lot of time thinking about that gap that exists between inspiration and action, right? Like, that's really where the rubber meets the road. And, you know, being somebody who lives on social media, and I'm always kind of looking at what other people are doing, especially thought leaders out there. And, and what I've seen particularly on Instagram lately is a lot of people putting inspirational quotes on pretty pictures and posting them. And, and I find that to be not helpful.

• 31:20Ryan Holiday?

  I totally agree. I think we know, I think we're probably thinking of some of the same people.

• 31:25Rich Roll?

  They get a lot of likes, but I'm thinking, is this actually getting anybody to do anything? Like, people will give you a thumbs up. And I think what happens psychologically is somebody reads that, and it gives them some kind of, you know, adrenaline or hormonal boost where they suddenly feel good for a moment. But they don't actually do anything. And then there's a sense of accomplishment that is, that is falsely placed. And I think it moves you away from actually making any changes in your life that are holding you back.

• 31:54Ryan Holiday?

  I think, I, I, I think about that a lot. I have a bunch of thoughts on it. There's actually a chapter in the book that I'm writing now that's all about this. But like, it, I think a couple of things. So, one, I think those people are being lazy. They're throwing out the quote because it's lazy, right? Because it's, it's easier to find a quote of someone else saying something smart.

• 32:09Rich Roll?

  If you have something interesting to say, go for it.

• 32:11Ryan Holiday?

  Although I hate when people quote themselves. I think it's like, like, you could just, like, I don't have to go like, uh, you know, "The obstacle is the way." Dash, Ryan Holiday. Like, I just say it. Like, you don't have to quote yourself. Like, it's implied. But, um, so I think they, they do that lazily because it's hard, it's easier than doing actual, creating some actual insight. And then it's rewarded by- Buy these fake internet points, which are hearts or likes or retweets or whatever. And then they feel like they they feel like they are making progress even though they aren't. And so I think that's a big part of it. But I I think the other I think the other thing is like. My rule for myself is like, I don't talk about projects until they're done.

• 32:51Ryan Holiday?

  Because it's so easy to, as the tools for making a thing have gotten much easier.

• 32:59Ryan Holiday?

  Like, anyone can say they're writing a book. Anyone can say they're creating an album. Anyone can say they're starting a blog or course or whatever. That's not the hard part. The hard part is making something so good that it breaks through the noise, or the hard part is doing the marketing so that it breaks through the noise. And like, I'm very much of the mind that like, it's not till it's done until you've actually jumped over that thing that you tell. Like, it's easy to train for a marathon. It's hard to do a marathon. But people, people have realized that if I say I'm training for a marathon on Facebook, I could get twenty, thirty percent of the validation from just saying that I'm going to do it. So why would like

• 33:38Rich Roll?

  Right, and then and then the next morning, when it comes time to go out and run, you're like, I don't need to, because I already got the validation.

• 33:44Ryan Holiday?

  Right, why actually, if actually doing it is very hard. And if I just talk about doing it, I can get a significant proportion of those same rewards. It actually creates a real disincentive. It's like illogical to actually do it for a lot of these people.

• 33:59Rich Roll?

  Well, that brings up an interesting, you know, uh, sort of discussion that we could have around goals and goal setting. And I want to get back to the inflection point of being on the stairs, because I think that's interesting as well. There's I had some thoughts on that. But, um, but, you know, in terms of setting a goal and then setting about achieving that goal. Uh, it brings up, uh, notions of, you know, accountability and and sort of, you know, these ideas of creating community around it that can propel you forward or dissuade you, like we just pointed out, like how that can actually distract you from the ultimate goal. Um, I think it is important to, you know, set a goal that scares you. But then to bring it back to Stoicism, it's about the process. It's not about that destination.

• 34:41Rich Roll?

  So when I set a big goal that scares me, whether it's, you know, doing Ultraman or, you know, writing a book.

• 34:48Rich Roll?

  As soon as I kind of put that on the calendar, however far away it is, I forget about that. And then it's just about what is in front of me to do today and embracing every aspect of that. Because it's about, it's about action, right? And I think at its core, that's really, you know, what Stoicism speaks to.

• 35:05Ryan Holiday?

  Yeah, it's, it's, it's ultimately a philosophy of action. It's not the secret, right? It's not like, oh, you wished for it, now it will become real. Certainly what you're wishing for and what you're thinking about has a real impact on your action. Like you said, like sort of what mood follows action, I think. I think that's very important, or action follows mood.

• 35:26Rich Roll?

  It's the other way around. Mood follows action.

• 35:28Ryan Holiday?

  Mood follows action. Okay, but I also think action follows mood, right? Like if, but then, in any case, action is, is the critical sort of variable, right? Like, what are you actually doing to get you towards what you're talking about? Like, what are you, what are the actual tangible steps that you're getting towards your goal? Like, one of the examples I talk about in the book, and I think is one of my favorite, and it was, it was weirdly controversial. I tell the story of like Amelia Earhart, who, you know, her first offer as a pilot, she was like, you know, she was a woman pilot, women could, had just earned the right to vote, not a great time to be a woman in America, especially like an ambitious woman. And her first offer for a transatlantic flight was from this rich donor who decided to sponsor a female flight.

• 36:12Ryan Holiday?

  But the offer to the woman was, a man is going to fly the plane, there's going to be a male co-pilot, and you have to sit in the back with the maps. But we're going to tell everyone that a woman, like, this is, everyone's going to congratulate you and think you're, you're famous, but you're really not. And like, to me, like, so I, I remember telling the story and I gave it at a talk recently, and this one woman got very upset, and you're like, dude, you're saying that she should have just, she should have just, you know, endured this like indignity, she just should have taken it? And I was like, yeah. Like, what she, what she did was she put her own ego aside. And she said, I'm willing to temporarily eat shit to advance my goals forward. And then from the, the platform and the, the money that she got from there, she funded her own.

• 36:56Ryan Holiday?

  Solo transatlantic flight like two years later and it made her actually accomplish what she was doing. But I see this like with my peers, like my college class graduated into the financial recession. And what most of them did was move back home with mom and dad or go to grad school because like the job market wasn't exactly how they wanted it. And like, so people now are like, oh, like you're so young. How have you accomplished these things? It's like, I'm not young, I've just been doing it long, like I've been doing it since I was 19 years old because I didn't spend an extra four years in school waiting for the job market to magically get better. And I, so I think a big part of it is like, can you put your ego aside?

• 37:36Ryan Holiday?

  Can you start small and can you actually like do the work every day regardless of what other people think, what other people say about it, what, what you think you deserve or are entitled to in life? Like it's that getting started that's sort of the step one that I think people don't like, partly because they have this idealized view of what the world is from these inspirational quotes that make them think it's like passion and inspiration and, and excitement that are the critical variables. It's like there's, I could, I could hire a hundred passionate people tomorrow. Could I hire someone I could actually rely on to do the work that I would trust implicitly and see real promise in? Probably not.

• 38:20Rich Roll?

  Right. But I think, you know, in your particular case, you had a very strong sense of direction early on, like your compass was pretty well calibrated about what you wanted to do. Not everybody has that, right?

• 38:31Ryan Holiday?

  Of course.

• 38:32Rich Roll?

  So I think first you have to, you know, do the, whatever internal work that you need to do in order to understand, you know, where your compass should be pointed.

• 38:41Ryan Holiday?

  Yes.

• 38:42Rich Roll?

  Um, and that's, you know, uh, an ephemeral amorphous thing that's, that's I think difficult for people. I mean, in my own personal life, like I never thought about any of that. I was on this track, I was going to be successful, you know, it's just, I was on the train to the mythical American dream where, you know, you study hard, you get into the best school and then. You know, I didn't know what I wanted to do, so I went to law school. Like, I just was propelling myself forward and I was, I was, you know, I could play that game, but never once did I take that moment of solitude to go, what am I doing? You know, what am I doing? So that's why I had to have this like midlife crisis over it. Like, you know, if I was 18 or 19 and maybe wasn't drinking so much, maybe I could have taken the time to think about these things.

• 39:23Ryan Holiday?

  Sure.

• 39:24Rich Roll?

  But I don't think that we, I think this is something that is very interesting about the millennial generation because for all the flack that millennials get, I think that as young people, they really are thinking about these things in a way that my generation didn't or was not encouraged to.

• 39:43Ryan Holiday?

  Yeah, I suppose, although like I hear from lots of kids, they're like, oh, will you be my mentor? Or like, oh, I want a mentor and they don't like, it's the, it's-

• 39:50Rich Roll?

  Well, the entitlement aspect.

• 39:51Ryan Holiday?

  Yeah, it's this idea of like, oh, sure, I'll give you this huge gift because you asked. That's how it works. It's like, no, like Sheryl Sandberg has this great quote. She's like, it's not about asking for a mentor, it's doing well and a mentor will seek you out. And I think it's hard for people, they're like, oh, I want to be a filmmaker. I want to be a writer, I want to be a internet celebrity, whatever they want to be. They think it's like the wanting to be it that is the important part. And so I think you're right, millennials have that figured out. What's harder is the idea of like, okay, so you have to get your ass kicked for five years before like-

• 40:26Rich Roll?

  Yeah, I don't like that part.

• 40:27Ryan Holiday?

  Right, like, look, I want to-

• 40:28Rich Roll?

  Or actually having something to contribute.

• 40:30Ryan Holiday?

  Like, I've always wanted to write books, but like I started a blog in 2006 and my first book in, my first book came out in July of 2012. And I didn't get paid for writing any time between there. I had plenty of book ideas, like it wasn't the book idea that I was missing. It was the anyone thinking that I, anyone actually wanting a book from me.

• 40:54Rich Roll?

  Right.

• 40:54Ryan Holiday?

  And that took six years of free work.

• 40:56Rich Roll?

  Right, right, right. Well, I mean, to kind of pick up on this idea of mentorship. I mean, I know, you know, your history is one of, you know, showing up to be of service and provide value to people that you respected without asking for anything in return, right? Which is kind of the, that's the antithesis of the entitlement generation. Like this idea that, you know, you have to bring something to the table and you have to trust and have faith that in some respect that that will pay dividends in the future, you know, towards the goal that you're trying to achieve.

• 41:28Ryan Holiday?

  Yeah, yeah, like I got an email like yesterday and this guy was like, hey, like, I want like you to mentor me. I'll work for you for free and then you can figure out if you want to pay me. And I was like, it's like, I think you understand the logic, right? That's the logic, but that's not, it's not a magical discussion. It's not a single life changing. Like I had this kid, I probably shouldn't talk about it, but this kid flew to us from Australia and showed up at my door. He just showed up.

• 41:53Rich Roll?

  Wow.

• 41:54Ryan Holiday?

  Because he'd heard that I was like looking for an assistant. And I know in his head, he was thinking, I'm gonna impress this person with this. He was thinking about his life as like this movie, right? Like this is, this is the, this is the midway point in the movie where the guy makes the decision that changes his life and then everything is awesome because he took this risk. And it's like, that's not how it works. And he didn't think about how that thing would be interpreted by me, which is that like, you think you're showing like passion and enthusiasm. I think you're showing like a lack of boundaries or like responsibility. And so I think, I think again, to tie it into these quotes, not to like beat on it, but like it's,

• 42:35Ryan Holiday?

  it's there's inspiration is a commodity. What, what the other things are how you differentiate yourself and you know, and, and how you, or like with running, like speed is great, but endurance is probably more important.

• 42:49Rich Roll?

  Mm hmm. Yeah, well, it's that it's a, there's a couple of things, a couple of thoughts that I had. I mean, first of all, I think that, that for somebody who is grappling with, you know, beginning a project, right? You hear Casey talk about this all the time, like filmmakers email him, how do I begin? How do I, how do I have your life?

• 43:07Ryan Holiday?

  Right.

• 43:08Rich Roll?

  They just have these grand ideas about, you know, they romanticize Casey's life and it's easy to do because he lives in a very dynamic life, right?

• 43:15Ryan Holiday?

  And he makes it look really good on, in movies. Like that's part of that's his job.

• 43:19Rich Roll?

  Yeah. But the first question is always like, what's the camera that I need to get?

• 43:24Ryan Holiday?

  Right.

• 43:25Rich Roll?

  As if that holds the key. And I think in a fitness context, it's about what's the watch that I need to get and what kind of heart rate. And all of these things are actually barriers to you actually doing it. And I think they are indicators, in my mind, of someone's fear of just starting. Like, they're overcomplicating something rather than just beginning it because they're afraid, right? So rather than just make a terrible movie or write a terrible book, they want to have a discussion about all of the artifice that surrounds those things, which actually is an impediment to them doing it in the first place. And so to use the example of the guy who flew out from Australia, I mean, he would have been better served to stay in Australia and figure out a way how he could

• 44:09Rich Roll?

  have benefited one of your goals from afar, and then demonstrated that he actually added value to your life in some respect without asking for anything in return. I think that would have been more impactful for him and maybe put him in a better position for you to say, "Sure, I'll employ you."

• 44:25Ryan Holiday?

  Yeah, totally, totally, totally.

• 44:27Rich Roll?

  So, all right, so inspiration into action. I mean, for me, pain is really the only thing that's ever motivated me to change any kind of my errant ways. And so in thinking about that, and understanding that we all have the facility to change at any given moment, that you don't have to suffer some, your elevator doesn't have to crash all the way to the bottom in order for you to be reflective on your life and make changes. I mean, what are some of the things that you found helpful in kind of turning a train around?

• 44:58Ryan Holiday?

  Like, pain in my life?

• 45:00Rich Roll?

  No, not, I'm saying, short of having to endure some kind of painful moment in order for you to do something different.

• 45:09Ryan Holiday?

  There's that great quote from Bismarck where he's saying like, Uh, like any fool can learn from experience. I prefer to learn from like the experience of others, which is something I've always like tried to live my life by. Like I think I've learned from a lot of mistakes from my mentors. Um, I've learned, like I obviously have read very widely and, and I'm always trying to think like, okay, like what I definitely, definitely don't want to do is wake up one day and go like, this is not the life that I want. Right? Like this is not where I want my life to be. I definitely don't want that moment. And so I, I think I've made a lot of decisions to avoid, like, you know, I dropped out of college. I quit really good jobs at various points. Um, and so I've definitely avoided that. And then of course,

• 45:51Ryan Holiday?

  you, you, you try so desperately to avoid something, but you end up just delaying, like this summer I woke up, I was, I was, I worked a lot on the sort of transition craziness at American Apparel over the summer. Um, when, when the, the founder was fired and who'd been a mentor to me. It was a whole period. And I, I remember waking up, like they were paying me really good money. I was, it was exciting. And then I, I woke up one morning and I was like, I, I, I went out to breakfast and I was like, fuck, like I gotta get to the office. And, and, and then I was like, wait, like my whole life, I made all these decisions, like about where I wanted to live, what I wanted to do, like that I wanted to be a writer. And here I am feeling guilty for like not being in an office. Like what, what is this?

• 46:33Ryan Holiday?

  Um, this is not what I wanted. And, um, and then I had, then I, and, and I had a similar, um, sort of, uh, realization about, uh, one of the partners in my company and it had become like a big deal. And, and so I had to then, I had to then detangle this like whole mess, like all these decisions that I'd made. Um, I had to sort of sit back and was like, what was actually motivating these decisions? It was, it was greed. It was like pain avoidance. It was like, like instead of having a conversation, a difficult conversation, I was like going along with things and all that was really doing was delaying the unpleasantness of what I ultimately needed to do. So I think it's interesting. I think,

• 47:14Ryan Holiday?

  like I've always tried to avoid, avoid having to learn from pain. And then I felt like what I really did was just delay it into an incredibly painful summer, which was last summer, that I'm only sort of now just kind of turned a corner on. So I don't know. I don't know. Does that really answer the question?

• 47:31Rich Roll?

  Yeah, I think so. I mean, but to then kind of apply the principles of Seneca and Marcus Aurelius to this, I mean, that was an experience that you weathered that I'm sure, you know, carries inherent value that you've learned from, right? So, you know, what is your perspective on that now? You know, was that bad? Was that good? I mean, it was just...

• 47:48Ryan Holiday?

  It was what it was.

• 47:49Rich Roll?

  It was what it was, right?

• 47:50Ryan Holiday?

  Yeah, and it showed me very clearly the things that I do want by making it clear all the things that I definitely don't want. And it will be, it's like I touched the stove. I got burned really bad. I'm not going to touch that stove for at least a pretty long while. You know what I mean? So, so in that sense, it was very beneficial. And, and the other thing is like, what's really nice about being a creative person or an artist is like, it doesn't matter how awful it was. Or even, even if I can never undo it, like it's, it just cost all this money. It was all this pain. It can never be undone. At the very least, you can turn it into material, which is so awesome about. Like, that's something Robert Greene said to me. He was like, look, it's all material.

• 48:32Ryan Holiday?

  So like, it doesn't matter that he had abusive bosses or, or that he got screwed over by this or that. It's like, these are the lessons that I then wrote books about. And so my next book is very much, it's not directly about the, the things I learned that summer, but I don't think the writing would be as good if I hadn't really, truly experienced it firsthand.

• 48:51Rich Roll?

  Can you talk about what that book is or will that defile your, your principle around not speaking publicly about your projects?

• 48:59Ryan Holiday?

  It's done, so I can talk about it a little, like it's in, in the realm of traditional publishing. It's turned in, but it won't come out until a year from now. But the book is about ego and how sort of we are ruled by this force that we don't want to acknowledge and we don't, like, nobody thinks they're an egomaniac, and I wouldn't say that they are, but they don't understand the way that ego sort of leads them further away from all the things that they want.

• 49:23Rich Roll?

  So give me an example of that.

• 49:27Ryan Holiday?

  So like, look, when you're, when you're young, being sort of delusionally ambitious can be adaptive in the sense that it helps you get over that uncertainty or unpleasantness of, of the scariness of what you're doing. But then, as soon as you are successful, that delusion is now your absolute worst enemy, right? Your, your inability to, and, and I would say like, like, look, one of, one of the greatest assets that I've had is that I'm always willing to like, learn from other people. And I'm always willing to take a sort of back, like, I don't need to be in charge because I'd rather sit back and learn from, from the situation. But if, if my disposition was a little bit different, if I'd started to say like, well, I've done X, Y, and Z, I should be in charge, all of

• 50:09Ryan Holiday?

  a sudden, that learning stops. All of a sudden, your ability to take feedback from, I think the most critical thing that an artist, or that an entrepreneur, or, or a business person has, is their relationship to the world around them, their ability to understand and interact with, and filter the reality that comes to them. And ego is, is a, is a wall between them and that reality. And that wall can be defensive sometimes, it can have benefits, but it's almost universally negative.

• 50:38Rich Roll?

  So then, how do you, how do you reconcile that against, you know, a, a survey of some of the most successful entrepreneurs out there who tend to, you know, you know, fall on the, you know, the spectrum of large ego and, and, you know, all the way to megalomania?

• 50:54Ryan Holiday?

  Well, there's a certain thing called the survivorship bias, right? Like, which I think is a big part of it. And I think another part of it is, is, is this idea of like, like, you could say like Lance Armstrong was successful because he was egotistical, right? But Lance Armstrong also had cancer. Was that why he was successful? Or like, correlation does not equal causation. I think that's a huge part of it. And then I think the other thing is like, there, I've met many, many successful people in my life. And I would say there's like, two or three of them that I would ever trade places with. So I think that's the other big part of it. It's like, we think these people have these lives because they've accomplished something that it must be

• 51:36Ryan Holiday?

  Meaningful, that it must be happy, that it must be what you want. And you don't realize that, that to get this thing, you think that you could, you could be the same person that you are and have this thing. And that, that's not how that trade works.

• 51:50Rich Roll?

  Right, we project idealized, you know, notions of what these people's lives are like.

• 51:55Ryan Holiday?

  Right.

• 51:56Rich Roll?

  You know, in an aspirational kind of way, but if you spend time with these, you know, and like, look, living in Los Angeles, I'm around a lot of really successful people. Most of which, not all of which, but most of which are really not happy people, right? And so we're sold this lie that, you know, success carries the seeds of happiness, which no matter how many times we're told that's not true, we persistently continue to believe that to be the case.

• 52:18Ryan Holiday?

  And I also find with those people that they're, the great work that they objectively have done came in moments of lucidity, like, like, cause you're, you were in the entertainment business. You see lots of creative people and everyone's like, they're fucking nuts. This person is insane, but it's in these moments when they're not nuts that they do great work, right? And, and everyone sits there and goes like, what could this person have actually accomplished? If they could have gotten out of their own way? You know what I mean? Like, like what, what great work could they have done? Or what huge failings and missteps could they have avoided? If they could have gotten a handle on their, their, their drug addictions? Or their inability to trust people? Or their, their need to one up everyone?

• 53:02Ryan Holiday?

  Or their inability to hear feedback? You know, like all these things. I think not only, not only do they prevent some people from being successful at all, but I think they also hold really talented, amazing people back from being even more successful or great.

• 53:18Rich Roll?

  Well, I think what happens is that, uh, you know, somebody who's in that situation holds on to that character defect and, and ascribes to that, uh, you know, part and partial of why they're successful, right? So, so, you know, the, the alcoholic or the heroin addict who's a, who's a painter, who thinks if I get sober, I'm never going to be able to channel any more creativity. Or if I don't throw temper tantrums, nobody's going to do what I say. Or if you're Steve Jobs and And you're not holding that like super hard line.

• 53:49Ryan Holiday?

  Right.

• 53:49Rich Roll?

  Then you're not going to be getting the excellence out of your team that you that you demand of them.

• 53:54Ryan Holiday?

  Right.

• 53:54Rich Roll?

  So the character defect becomes the recipe for success. And that belies this sense of, you know, this elusive sense of balance that perhaps, you know, if you look at it in a longer term, might might fuel a better outcome ultimately.

• 54:09Ryan Holiday?

  Yeah, I mean, you talked to plenty of addicts who came out the other side and they're like, look, I'm just, that was my huge fear. I'm more creative now than I was before.

• 54:16Rich Roll?

  Yeah, I hear that all. I mean, I'm around a lot of those people and so I've experienced that firsthand. But the fear is so palpable.

• 54:22Ryan Holiday?

  Totally.

• 54:23Rich Roll?

  That that it that it prevents embrace of that idea.

• 54:26Ryan Holiday?

  And it's not just fear. It's also, I think it's your dependence or your like, whether it's a character trait or an addiction, it's your comfort with the status quo that is rationalizing the change, rationalizing the resistance to change. It's like, oh, like, well, it's like, look, it's not that you're afraid of being creative. It's that you really like doing drugs and you don't want to stop doing drugs.

• 54:49Rich Roll?

  Right. Well, that's the lie.

• 54:50Ryan Holiday?

  Right. Yeah.

• 54:51Rich Roll?

  That's the lie that's that you want to just buy into completely.

• 54:54Ryan Holiday?

  Right.

• 55:02Rich Roll?

  All right. So that's interesting. So so basically, the the underlying premise behind that is if you can squelch the ego or rein it in, that ultimately you could be more productive. And so what is what's behind that?

• 55:15Ryan Holiday?

  Yeah, I mean, like, so look, one of my favorite, one of my favorite historical figures period is George Marshall. So you look at George Marshall, that he, so he's the chief of staff during World War II. He wins the Nobel Prize for the Marshall Plan. He's a he's a diplomat. He does all these amazing things. Most people have no idea who he are, who he is. They have heard of MacArthur or Patton, these sort of very, very egotistical generals. And And but who ultimately had a much bigger impact on the world? It was this humble guy who he didn't keep a diary because he felt like keeping a diary would make him perform for history. He wouldn't, he turned down a million dollars for his memoir because he didn't want to embarrass anyone.

• 55:59Ryan Holiday?

  There's this story where like he's forced to sit for this uh like official portrait. And he goes like two or three days in a row and then he's the guy's like, okay, you're done. And then he gets up and he leaves and the guy's like, wait, don't you want to see your painting? And he's like, no, like why I know what I look like. You know, it's this idea of like, if you can, if you can become as self-contained as possible and is as unreliable on these sort of external factors, these sort of ego hits that we need, it actually allows you to do much better work. Not just much better work, but much more selfless work and much, um, much less sort of um, encounter much less resistance on that work. And I think you ultimately have a greater impact on history, on the world and on sort of fulfilling your personal potential.

• 56:43Rich Roll?

  Humility.

• 56:44Ryan Holiday?

  Totally.

• 56:45Rich Roll?

  It's humility and being service oriented.

• 56:47Ryan Holiday?

  Totally. The problem is no one will read a book about humility because humility sounds boring. Like I, I think, and so this is something obviously I think about as a marketer, but it's interesting like, like, we all know that humility is like where we want to end up, like we want to be a humble person. But nobody thinks that humility will get you there. Like you're like, look, I want to have this.

• 57:04Rich Roll?

  Weakness.

• 57:05Ryan Holiday?

  Right. You're like, I want to have this nice house and I want to have a, an audience and I want to have all this stuff. And I want to be humble and well adjusted when I'm there. And then you tell yourself that you have to be a fucking dick who screws everyone over or puts, you know, does things you don't agree with or like in order to get there. And I think that's probably not true.

• 57:25Rich Roll?

  No, I think, I think you're absolutely correct about that. I mean, I think that that requires um, a level of faith that I think most people don't have the facility for. Because you have to approach whatever it is you're doing from a perspective of service rather than, you know, in, instead of approaching whatever it is, your career or whatever scenario you're walking into and saying, what am I going to get out of this? And saying, what am I contributing to this?

• 57:51Ryan Holiday?

  Sure.

• 57:52Rich Roll?

  And, and, and really divorcing yourself from the idea of how you will be rewarded. I think ultimately is like the secret to long-term success. And that requires. Reigning in your ego and it requires really grappling with who you are inside of yourself. Can you get to that place where you really are outside of what it is that you want and you are truly in a place of just serving, right? And I think that when you do that, the path unfolds naturally in front of you and creates the decision tree where the moves that you're going to make naturally unfold. But it's not, it's an ephemeral idea, right?

• 58:32Rich Roll?

  And I think you can anchor it in the mystic of the moment or whatever kind of spiritual principles or read the Bhagavad Gita and like all of these kind of ancient texts will resonate with this notion, but that's not really part of Western culture and the ethos around success.

• 58:55Ryan Holiday?

  Well, let me ask you, because I remember reading, so was it your first Iron Man? It was, what did you place?

• 59:01Rich Roll?

  I did Ultraman in 2008 and I was, I got 11th in that or I think I was the second fastest American. That was in 2008.

• 59:10Ryan Holiday?

  Yeah, so if I remember correctly, you weren't even sure you were going to be able to compete, to finish it, right?

• 59:16Rich Roll?

  No, I just didn't want to die. Yeah, like I didn't, I wasn't there to race it. I was there to celebrate this kind of change in my life.

• 59:22Ryan Holiday?

  And so I remember reading that and thinking like, do you think you would have done better or worse if you'd gone in with an idea of what you were going to, like if your goal had been to get second, do you think you would have gotten second?

• 59:36Rich Roll?

  No, there's no way. There's no way. I mean, I think that when you're approaching something like that, like I was coming from a place of I had never done an Iron Man, you know, I was not like I had no pedigree as an endurance athlete and I approached that race with I think an appropriate level of humility because it was so overwhelming. And I think there's something in particular in a mystical sense about the big island, you know, like there's, you know, if you want to talk about the Kahunas and all of that and like the kind of, you know, all the sort of spirituality that surrounds Hawaii, like it will force you to your knees. And I think if you approach that race with a sense of ego or entitlement, you will be

• 1:00:18Rich Roll?

  reckoned with in a very gnarly way and you will hear that with any of the Iron Man champions. Like if you talk to Chris McCormick or Mark Allen or Dave Scott. You know, all of them were insanely talented and, you know, sort of were winning races all the time, like Macca talks about this all the time. So, you know, he was like king of triathlon, he'd won every distance. And so he just thought like he was going to go to Hawaii and he was just going to walk away with the Ironman, you know, world championship title, no problem. There was no reason why that wasn't going to happen.

• 1:00:47Ryan Holiday?

  True.

• 1:00:47Rich Roll?

  And it just crushed him. And it took him years and years and years of going back and studying before he could finally master it and win it. And he had to learn, you know, he's a very, he's, the guy's got a big ego, he's a very dynamic personality, but he had to be, he had to get to a place of humility before he could really come out on top of that. And I think that's a powerful lesson, you know, because he, because he has such a big personality, that he had to weather that makes it all the more beautiful.

• 1:01:15Ryan Holiday?

  Yeah, there, I quote Mike Tyson in the Stoicism book where he's like, if you're not humble, life will visit, will visit humility upon you.

• 1:01:23Rich Roll?

  Right. And you can't escape that.

• 1:01:25Ryan Holiday?

  Yes, although the more humble you are, the less likely that will be a catastrophic lesson in humility.

• 1:01:32Rich Roll?

  Right, right.

• 1:01:32Ryan Holiday?

  Versus like a, oh man, like that was embarrassing, I shouldn't do that again.

• 1:01:37Rich Roll?

  Right.

• 1:01:37Ryan Holiday?

  Like, like, um, cause Neil Strauss was telling me this idea of a two cars in the garage addict, which is like the addict who can get sober before they end up homeless.

• 1:01:49Rich Roll?

  Mm hmm. And that's the trick.

• 1:01:50Ryan Holiday?

  Right.

• 1:01:51Rich Roll?

  You know, like when I'm talking about like pain being my motivator and having that inflection point on the staircase, you know, I was in enough pain where I was ready to like do something about it. And it, and what happened on that, in that moment was that it reminded me of the day that I woke up and, and was ready to get sober. And I think there's something precious about these, you know, very discreet moments in time where the door cracks open and there's a window of opportunity and, and you have the ability to act and act swiftly and decisively in that moment, or it passes and you don't know whether that moment is going to revisit you. So I understood on the staircase that I was getting another chance like that because when I woke up that morning and decided to get sober, it changed my life so dramatically.

• 1:02:33Ryan Holiday?

  Right.

• 1:02:34Rich Roll?

  But had I just blown it off or said, I'll deal with it. Tomorrow, who knows whether I would have ever made that change. So there's something very special about that. But can you make that change short of having that kind of experience? Can you do it when you have, when the elevator, perhaps you have a perception that your elevator is going down or the train is moving in the wrong direction. But before, you know, it crashes into the ground, can you redirect?

• 1:02:58Ryan Holiday?

  Yeah, I think it's the more sensitive you are to the feedback that the world and reality is giving you. Like you got to feel out of breath was enough for you to say like, hey, something is not right. Rather than heart palpitations or, you know, a diabetes diagnosis. Or, you know, like any, any number of the much more severe signs that you could have gotten. Like, yeah, like for me, like this summer, it's like I had this wake up moment. But like, it could have been when my wife, like it could have been because my wife left me.

• 1:03:26Rich Roll?

  Right.

• 1:03:26Ryan Holiday?

  Or it could have been, you know, that I turned in my book and the editor was like, this is shit. Like where you were working on this, what hap- you know, like it could have been a, the wake up call could have been much worse. And like what I saw this summer with Dove was like, like, I mean, what, what happens when you get fired from the company that you founded and legally barred from ever reentering it? Because, you know, you, you blew past so many intersections and stop signs and red lights and warning signs and police blockades and every other thing that could have told you like, do not do this. You blew past and then you lost everything.

• 1:04:09Rich Roll?

  And I'm sure he would tell you that, that those, those character traits were part and parcel of what made American Apparel successful to begin with, right? So the seeds of destruction are planted, you know, in the same fertilizer as the ones that, that allow it to flourish.

• 1:04:24Ryan Holiday?

  No, I mean sadly even worse, he would tell you that he was screwed over and he's going to get it back. And it's not.

• 1:04:32Rich Roll?

  So he's not learning the lesson?

• 1:04:34Ryan Holiday?

  No, not, not even close.

• 1:04:35Rich Roll?

  Right. So, so, you know, similarly, if you look at Lance Armstrong, you know, it's a very similar case, right? You could say. However you fall in that discussion, and there's a million opinions, and I don't presume to have a strong opinion one way or the other. I think it's far more gray and nuanced than

• 1:04:54Ryan Holiday?

  I agree.

• 1:04:55Rich Roll?

  People want to admit or embrace. But the character traits that made Lance Armstrong a champion were also the ones that sowed the seeds of his destruction, right? So if he hadn't decided to make a comeback, you know, this would have never happened.

• 1:05:11Ryan Holiday?

  Right.

• 1:05:11Rich Roll?

  And if he had decided not to screw all those people over along the way, those chickens wouldn't have come home to roost. But it was because of that very behavior pattern that propelled him into that rare air that allowed him to be so successful in that domain.

• 1:05:29Ryan Holiday?

  Yeah, one of my favorite, I've wrote about this a long, long time. One of my favorite books is Fight Club. And the premise-

• 1:05:34Rich Roll?

  It's incredible.

• 1:05:36Ryan Holiday?

  The premise of Fight Club is that he's living a horrible miserable life, and he cannot see it. And so his alter ego, or him while he's asleep, has to blow up his apartment with everything he ever loved inside of it. And even that is not enough. You know, like, so I call them these like sort of Fight Club moments, where someone calls you out, or someone blows up your stuff, or you fail. And it's like, you can, it's in those moments that you see truth, right? And you can decide whether you're gonna look at it in the face, or whether you're gonna avert your gaze and go right back to doing what you're doing. And I think, you know, the longer you put it off, the more dark and unpleasant that

• 1:06:18Ryan Holiday?

  truth is gonna be. And paradoxically, the harder it's gonna be for you to accept it. It's cognitive dissonance, right? Like, nobody wants to, you think you're a good person, it's very hard for you to accept that you've done a bad thing, or that you've messed up, or that you're bad, or any of these things.

• 1:06:34Rich Roll?

  Right. Absolutely, unquestionably. My wife calls it your divine moment.

• 1:06:41Ryan Holiday?

  Sure.

• 1:06:42Rich Roll?

  Right? And it's your reckoning.

• 1:06:44Ryan Holiday?

  Yeah.

• 1:06:44Rich Roll?

  And are you gonna wake up and heed that call? Or are you gonna blindly propel yourself forward until it gets worse and worse and worse? And there's something, you know, to bring it back to Stoicism and the obstacle is the way. This is an obstacle that you face in your life that could be the most beautiful, you know, rebirth and flowering for your life if you're willing to face it head on and accept it and deal with it objectively and really kind of grapple with who you are to then set yourself forward in a new trajectory, or you can blow it off, right? And like, that's been my experience. And so, you know, those divine moments bring you to your knees and we as, you know, people living in America will immediately label

• 1:07:26Rich Roll?

  that as tragic or disastrous, or this is the worst thing that's ever happened to you. But I'm sure, you know, I know, and I'm sure you know many people have experienced this yourself, where you look back on it five years later and you're like, that was the greatest thing ever. Like, look where I am now because of that thing that forced me to look in the mirror in a new and different way.

• 1:07:44Ryan Holiday?

  Yeah, and not that every moment is gonna be so dark and terrible, or that every obstacle is gonna bring you to your knees. Sometimes it's like, hey, I thought this would work. It didn't work. But what are you gonna do about it? You know what I mean? Or like, hey, this person is being an asshole. Am I gonna be an asshole back to them? Or am I gonna use this as practice for dealing with assholes?

• 1:08:03Rich Roll?

  Yeah, there's the macro and the micro, right? And so, you don't have to suffer some cataclysmic, you know, result in your life.

• 1:08:10Ryan Holiday?

  Sure.

• 1:08:10Rich Roll?

  These obstacles come in the form of, you know, the person who cut you off on the highway, or, you know, your boss being a douche, or whatever. Like, how are you navigating that? Like, are you being reactive? Are you being of service? What kind of humility are you bringing to that equation that ultimately might, you know, provide you with a different result? Like, in recovery, they call it contrary action, right? Like, you have these behavior defects, you're reactive, people push your buttons, you generally do this, and this gets you that negative result. What is, you know, do the opposite of that? Like, can you retrain your brain to act differently? And for me, that comes back to, you know, meditation and other ways of trying to rewire, you know, the brain and the personality to behave differently.

• 1:08:54Ryan Holiday?

  Yeah, right. Can you, can you not, can you be more than the sort of like a reactionary robot, right? Like, this is what I normally do, so I'm just gonna do that. Even, even if all evidence points to its ineffectiveness.

• 1:09:10Rich Roll?

  Right, right, right, right. Have you read Sam Harris's Free Will?

• 1:09:14Ryan Holiday?

  No, I love Sam Harris.

• 1:09:16Rich Roll?

  Yeah, you gotta, you gotta read it. It will bend your mind about decision-making and our capacity to, to, to make decisions, you know, well, we can talk about it later. We can go down a rabbit hole on that, but read that, you should read that.

• 1:09:32Ryan Holiday?

  Okay.

• 1:09:35Rich Roll?

  Well, from here, like, I want to talk about maybe some, some, you know, practices that you found helpful. Perhaps they're morning routines or things that you do on a daily basis that help keep you kind of in check. Maybe they're things that help remind you of your humility and

• 1:09:54Ryan Holiday?

  Yeah.

• 1:09:54Rich Roll?

  keep you in that service-minded set or kind of help you focus on, you know, confronting and overcoming those micro obstacles that you face on a daily basis.

• 1:10:05Ryan Holiday?

  Yeah, it's weird. I think one of the things about the books that I've written is that like, the natural assumption is like, oh, he's writing about this because he's like, he's some sort of expert. But really, I'm writing the book because like, it's for me. And then I just happen to sell it to other people at the same time. Do you know what I mean?

• 1:10:19Rich Roll?

  Uh huh.

• 1:10:20Ryan Holiday?

  So like, I, I, for me, like, the books are actually hugely therapeutic, sort of huge, hugely necessary like codification of these ideas. And I actually like, it sounds weird, but I like read my own books. And like when I'm, it's like, because I don't see myself in them. I see smarter people than me organized in a way that's more accessible for me. But like, like I journal every morning about the day before. I try to meditate like, you know, 10 or 15 minutes a day. I'm not very good at it. It keeps me very. The idea of not doing anything is like very hard for me. And so I've actually spent like the last year like trying to like say no to things and trying to actually like Louis CK

• 1:11:01Ryan Holiday?

  talks about these like moments where you're uncomfortable and your first instinct is like reach for your phone or do something instead of like sitting with that discomfort.

• 1:11:11Rich Roll?

  It's it's the hardest thing.

• 1:11:12Ryan Holiday?

  It's the hardest thing. It's so awful. It's like antithetical to, I mean, who deliberately feels uncomfort discomfort and like we have these magical sort of like solves in our

• 1:11:23Rich Roll?

  Right.

• 1:11:23Ryan Holiday?

  pockets at all times.

• 1:11:24Rich Roll?

  Right. Like, standing in lines is no longer a problem because we all have a phone and we can, you know, distract ourselves.

• 1:11:30Ryan Holiday?

  Yeah, yeah. And so I like I've I've spent a lot of time trying like, like, I don't check my email until I've journaled and done at least one other thing every morning. So that there's like, um, there is time that I'm awake, that the world is mine and no one can impose on it. And and I've tried to sort of like exercise is that moment for me too. So it's also why I don't try to make it happen as fast as possible. And I'm not looking for shortcuts or like hacks to make it more effective. It's like, I like what it is. And I like that it's time that I'm not plugged in. So that those are the sort of things I think about. And Stoicism is really, it's, it's this set of exercises and

• 1:12:13Ryan Holiday?

  meditations, right? It's the idea of like, it's reminding yourself in some situation, like, there is not a good or bad here. There is my perception about that thing. And every time cognitive behavioral therapy is is that idea of like, here's what happened. Here's my normal reaction, like you said, is is that and then putting that beat there. So you can say, is that the reaction I want to consciously allow in this situation? It's like, like this happened, here's my emotion. Is that a positive or a negative emotion? Am I gonna like sort of give into it? And so for me, it's been a lot of work about creating that the ability to have that control over my thing. So it's like, maybe I got

• 1:12:54Ryan Holiday?

  mad, but two seconds later, I'm aware that I'm mad and I'm gonna stop being mad and I'm gonna apologize for being mad. And I'm gonna reset.

• 1:13:02Rich Roll?

  Right, right. A friend of mine calls that. If you're gonna eat crow, eat it hot.

• 1:13:07Ryan Holiday?

  Yeah, sure.

• 1:13:08Rich Roll?

  Right. So if you had to inventory like your, your character defects or the things that you struggle with that you're still trying to overcome, and what would that look like?

• 1:13:17Ryan Holiday?

  I think intensity is my biggest one. Like even now, I'm like all over the place. I'm like getting excited. Like it's that intensity which is like a benefit to me. It's made me good at what I do. But it's also problematic when most people are not that intense. And so like if I'm quick to something and I'm intense about it, all of a sudden a very minor thing can get, become a very major deal very quickly because I've thrown, like the other person has thrown two seconds of thought at it. And I've thrown my entire intellect behind this thing and what it means and whether I like it and whether I'm gonna accept it and whether what I should do about it and what it means and all this

• 1:13:58Ryan Holiday?

  blah onto a pretty everyday, you know, human interaction.

• 1:14:05Rich Roll?

  Right. So you're kind of, you're, you're kind of putting gasoline on the, on the flame.

• 1:14:09Ryan Holiday?

  Yeah. And, and so I, I think about that too with the discomfort where it's like, if I don't feel like doing anything, maybe I don't have to do something. I don't have to respond to a feeling of fatigue or, um, you know, frustration or, you know, lack of progress. I don't have to like, like I, I go to therapy and my therapist, she's like, Ryan, like thoughts are not facts. Like just because you thought about doing something or you wanted something to happen does not mean that it must happen. And that's, that's something I've spent a lot of time on recently is it's just this like, relax, like every, it's, it's 85% how you want it.

• 1:14:51Ryan Holiday?

  To, to think that you, that, to make yourself miserable about that 15% is like a very.

• 1:14:59Ryan Holiday?

  Needless compulsion.

• 1:15:00Rich Roll?

  Mm hmm, mm hmm. And how does running play into it? I love that post that you wrote on, on, on, I don't know what it was called, Why I Run or something like that.

• 1:15:08Ryan Holiday?

  Yeah, yeah. Um, running is, running is, is really good for me. And then also I can see how it's bad for me in like the sense of, um, it's, it's a time where I'm not connected to like any device other than like music. Um, it's, I'm doing something that's like good for my health. I'm, I'm doing a lot of thinking. I, I get into a flow state when I run and, and so that's really great. But on the other hand, it's like, like, I'm, I can see myself like, it, it was once an activity that I loved. And then I, you can ritualize something like that and make it an obligation, which strips it of its purpose and meaning. So it's like, like, you know, I was thinking about like, cause I'm, I'm out here and I had to get up early and then, um,

• 1:15:52Ryan Holiday?

  doing some other things today. It's like, I'm, I like, I have a bit of anxiety about whether I'm going to be able to run or not. Not like, I really want to run and I should be able to, but it's like, like, am I failing if I don't? Like, am I letting myself down? That is not a healthy relationship with an activity.

• 1:16:09Rich Roll?

  Mm hmm. Yeah, that's interesting. I mean, I definitely struggle with that as well. Right?

• 1:16:13Ryan Holiday?

  I'm sure.

• 1:16:14Rich Roll?

  The thing that, the thing that brings you joy can be, can be, can be undermined by the sense of, of, you know, obligation, to use your word, um, to do it. Yeah, that's interesting.

• 1:16:26Ryan Holiday?

  I, I turn everything into work. That's my sort of demon, right?

• 1:16:30Rich Roll?

  So like. Now we're getting it.

• 1:16:31Ryan Holiday?

  Yeah, like, so I work, like, or sorry, I love reading, but if I'm not reading, like, it was only until recently that like, I could go like five or six days without reading because I was busy or I wasn't into it. And I didn't feel like I was like cheating myself or letting myself down. Um, and so it's like the same with running, like, so for me, the discipline would be decide like today is Sunday. I'm spending time around the house. I'm, I'm going to commit to not running. You know, like, so that's, that's the, the harder part for me.

• 1:17:01Rich Roll?

  Yeah, yeah, yeah. I totally relate to that. It's interesting because most people are looking for the motivation to run.

• 1:17:07Ryan Holiday?

  Sure.

• 1:17:08Rich Roll?

  And, and for me, it's being okay with the fact that perhaps it's not going to happen today, you know? And like, you know, I'm in this transition right now where, you know, I'm sort of known as this athlete who's done these things. And, and now I'm kind of maturing into a different kind of thing where it's more about advocacy and like doing the podcast and the next book and all that sort of stuff. And. And you know, I have four kids and I have, you know, like I want to be happy in my life. And, uh, you know, perhaps if I lived in a cabin in the woods, I would train all day long and just write, and I would be content in doing so, but that's not my life. So how do I have all of those things in balance in my life and be happy with that? And I don't, you know, I don't think that going out and training 25 hours a week right now is really the right thing for me to be doing. Maybe it will be in a couple of years.

• 1:17:53Ryan Holiday?

  Right.

• 1:17:53Rich Roll?

  Or get, you know, thinking of some crazy new challenge because I, I worry about, am I still going to be relevant if I'm not, you know, out there doing one of those things? Is there a new way to, you know, to redefine what I'm doing? What makes sense? What's the best way to carry a healthy message? Um, and, and that can become burdensome.

• 1:18:10Ryan Holiday?

  The Stoics talk about this a lot and I've, I've been reading about it and like, he's like, there's this one line where Marx read this, he's like, "Take the people who felt the most intense anger or passion or drive to do something in history." And he's like, "And where are they now?" He's like, "They're dead and that has dissipated." Um, and so it's like, you know, you have this emperor who was the most famous man in the world and now even, even 50 years later, people barely remember his name. And so it's crazy to, to have this Marx realist who's also that person. It's not, it's very easy for a nobody to say like, being famous is meaningless. It's, it's much more powerful when an actual famous person is sort of talking about what these things mean. And so he like, I think that one of the things I've had to start to remind myself of is like,

• 1:18:54Ryan Holiday?

  "Look, you're not building some fucking monument here for all time that like, and even if you were, you would be dead and you wouldn't know that people appreciated said monument." So it's like, if you're not enjoying it now, that's not good. And you've got to think about that. And so sometimes like getting a reminder of your own mortality helps you relax a little bit. You know, because you, it's not, it doesn't make things meaningless, but it helps you go like, relax, like you're doing fine, like you're doing better than most people. You've accomplished this stuff, you should be proud of it. You don't need to feel shitty because you haven't done enough. So that's a big thing for me. And then the other thing for me is, is you want to look at like, you know, look at your friends, look at your family, like my- My parents live in Hawaii and when I go and visit them, they're just like, we gotta do this, we gotta do this.

• 1:19:37Ryan Holiday?

  My parents are just total activity addicts. Like, I love them, but like, my parents live in paradise and all they wanna do is activities all the time instead of enjoying the fact that they live in this place. And like, clearly, I internalized that as a kid. And so now I live in like my version of paradise in Texas and like, like my, my wife will go out and it's like, sit and be surrounded by animals or just like, look at things. And I'll be like, like, we, we have a pool. I've never had a pool before. And like, I get in the pool and I'm like, what are we doing? Like, should we do laps? And she's like, no, we're in the pool. And I'm, I'm like, I don't get this. Like, I don't get what, what are we doing? Like, this feels so weird to me.

• 1:20:21Rich Roll?

  Right.

• 1:20:21Ryan Holiday?

  But I'm trying to learn.

• 1:20:23Rich Roll?

  Infusion of Eckhart Tolle.

• 1:20:24Ryan Holiday?

  Yeah, right. Like, you can actually be in the present moment and not do something and that is just as meaningful. Like, why is, why is me spending 20 minutes swimming from one end to the other? Somehow, in my mind, a good use of time, but standing in the middle of it feeling nice is like heretical waste.

• 1:20:46Rich Roll?

  Right. Well, that's the, uh, that's the plight of modern man, I think, right? And I think that is, that's what's propelling so many people to be miserable.

• 1:20:55Ryan Holiday?

  I don't think it's the plight of modern man, because I think other people have no problem watching seven hours of television on average a day. So I think it's, it's the plight of certain modern men.

• 1:21:03Rich Roll?

  But that's, but that's not being present. That's, that's, that's like, you know, that's like taking a drug. You know, that's escaping your reality rather than like embracing just the moment that you're in and appreciating it. You know, and to your point about death, I mean, I don't think that we talk about or think about death enough. You know, I think we should objectively be quite aware of that in every moment. And I think that that would give our lives more context and meaning. But, you know, again, it goes back to, you know, these cultural paradigms where we're, we're all walking around thinking that we're gonna be the exception, that we're not gonna die or, and even when somebody is on their deathbed trying to, you know, tell them that it's actually not going to happen as opposed to just appreciating it,

• 1:21:46Rich Roll?

  I think would give, would infuse our lives with, with a lot more kind of appreciation and gratitude.

• 1:21:51Ryan Holiday?

  Yeah, there's this great line from Marx's realist, we're saying like, um, Alexander the Great and his mule driver were both buried in the same ground. And it's like the same, the same thing happened to both of them, which is that they died. Although one of them was murdered by his own soldiers. So you gotta ask like, who is, who, who had a better end? And then they're both buried in the ground and then, uh, you know, it doesn't mean anything to Alexander the Great that Alexandria still exists and is named after him. He's fucking dead and he's been dead for a long time. Like he doesn't, he's not just sitting there like, you know, enjoying it, like he's gone. And so, you know, he probably was a super miserable, awful person. It just seems like, you know, centuries later, like, oh, I want that, but you don't want that. I promise you, you don't want it.

• 1:22:36Rich Roll?

  How to be present.

• 1:22:37Ryan Holiday?

  Yeah.

• 1:22:38Rich Roll?

  The most difficult thing, right?

• 1:22:40Ryan Holiday?

  Totally. I mean, no, surviving is much more difficult, you know, the obviously much more difficult things, but in the first world, being present is the most difficult thing.

• 1:22:48Rich Roll?

  First world problem. Yeah, yeah, yeah, for sure. All right. Well, let's shift gears a little bit here. I can't let you, I can't let you out of here without talking a little bit about, um, marketing, which is the other side of, you know, kind of what you do.

• 1:23:01Ryan Holiday?

  Sure.

• 1:23:02Rich Roll?

  Um, and, you know, it's kind of interesting what's going on right now. Uh, you wrote an interesting piece about the, the recent, you know, Gawker episode, uh, where they, where they outed, the, uh, the CFO of Conde Nast for an indiscretion. And it kind of speaks to our, our schadenfreude, you know, uh, obsessed culture and kind of where media is going right now. And, you know, is there, like, how are we, you know, how is this going to play out? Like, is it just getting worse and worse?

• 1:23:36Ryan Holiday?

  I think it's getting worse, but I, I do think in the last year you have, I think the fact that people are angry about this Gawker post is the result of like some great work from people like Monica Lewinsky has that awesome TED Talk about shame. Um, John Ronson's book is amazing.

• 1:23:51Rich Roll?

  Yeah. And he's been doing the podcast rounds and like, I love that guy.

• 1:23:54Ryan Holiday?

  Oh, he's fabulous.

• 1:23:56Rich Roll?

  And I'm so glad that he wrote that book.

• 1:23:58Ryan Holiday?

  That he could write a book about people that you hate and make you feel empathy for them is what, like, literature, there's great studies that show that literature increases empathy and that's what his book does. And so I think like, look, if you, if you want to improve the quality of your life right now, you're looking for some life hack to like improve the quality of your life. Um, stop watching the news or like current, current event.

• 1:24:25Ryan Holiday?

  Oriented content because 98% of it does not affect your life in any way. It changes your perspective on things and it frees you up to do to focus on the fact that for 5,000 years, really smart people have been writing things about timeless subjects and you know timeless wisdom that you should be it's like once you've read all the classics, then fine read Gawker in the morning, but you haven't. So what are you doing? You know what I mean? So I think like from a media and marketing are very different, but I am very bearish and disappointed in our current media system. I think it's really bad. Of course, there's also some marketing opportunities within that, but it generally, I think Gawker is a force for evil in the world that has been tolerated by society for far too long.

• 1:25:09Rich Roll?

  Right. Well, systemically, it's, you know, it's wired to be that way because the entire foundation upon it is premised upon page views, right? And so when, when that's the case and it's, you know, driven by ad sales on page views, then you're going to get cats and you're going to get, you know,

• 1:25:27Ryan Holiday?

  Yeah.

• 1:25:27Rich Roll?

  Inspirational quotes.

• 1:25:29Ryan Holiday?

  Yeah, like all this stuff that is complete nonsense and is not really advancing our, you know. Sure. But also like, you know, our response to drugs or other addictions is a, is a biological mechanism. That doesn't mean that you should be a drug dealer or you should do drugs. And I think that's, that's how I see a lot of the like Gawker was saying, oh, people want this. Well, people want a lot of stuff. That doesn't mean you should give it to them or that it's good that they have it, you know? And I'm not being paternalistic. I'm just saying like, um, we only have so much time on this planet. Are you going to waste it consuming crap? And are you going to waste it producing more crap that we don't need? Not great.

• 1:26:08Rich Roll?

  So how do we shut it off?

• 1:26:09Ryan Holiday?

  Uh, read books. Read books, I think is a big one. I, there was this, I got in this spat a couple of days ago with like an infomarketer friend who he put out this quote, he was like, you should spend 20% of your time producing 80% of your time marketing.

• 1:26:24Rich Roll?

  Uh huh.

• 1:26:25Ryan Holiday?

  And I was like,

• 1:26:26Rich Roll?

  I hate that.

• 1:26:26Ryan Holiday?

  I was like, I'm a marketer. This is what I do. And I'm telling you that is the biggest crock of shit that I've ever heard.

• 1:26:38Rich Roll?

  All right, so let's camp out here for a second because I get insane about this kind of thing. And you know, as somebody who, you know, who, again, I'm some, you know, I'm kind of like living my life on social media and I'm kind of in this health and wellness space. And so I pay attention to a lot of the quote unquote "thought leaders" that are, you know, making waves in this world. And so I subscribe to all their newsletters and I just kind of try to, I try to, you know, analyze kind of what they're doing and how they're pursuing their business because I'm trying to think about how I'm cultivating a responsible profession around what I'm doing, right? And I'm just dismayed, you know, I'm dismayed, you know, I get these, these auto responders

• 1:27:19Rich Roll?

  and these emails and I get stuck in these, you know, these labyrinthine, you know, kind of email chains that I can't escape from. And just the pure language of it is so disappointing to me. It's all, it's all like clickbaity, you know, BuzzFeed gawkery kind of language where like, here's the blog post no one wants you to know about, like, I just found out the secret and, you know, you could do it if you click here and then there's always an upsell and all of this kind of stuff. And I'm like, I was talking to James Altucher about this and I was like, like, how do you as somebody who is a writer online, you know, and somebody who understands implicitly marketing and has an audience, like, what is your perspective on this? And he said something very interesting, which is like, you know, he, he finds it distasteful

• 1:28:02Rich Roll?

  as well, but he said, when you, when you test it, it's like not even close. It's like nine to one in terms of how people, you know, kind of respond to it.

• 1:28:13Ryan Holiday?

  It's, that's true and I love James's stuff. And he was a client and a friend of mine too, so I wouldn't say, I wouldn't disagree with him. But what I would say is like, first off, look, saying you're too good for this, that's a problem, right? Where people are like, oh, you just gotta make something amazing and it'll take care of itself. That's a delusional attitude.

• 1:28:30Rich Roll?

  That is delusional also, but I think this, what I see is all of these people who are spending all of their time on marketing and, and almost no time on creating anything of any value or quality.

• 1:28:41Ryan Holiday?

  Well, that's what I was gonna say. I think the other people on the other side of it are responding to overwhelmingly short-term incentives and building nothing that will last.

• 1:28:49Rich Roll?

  Right. The most important thing is building an email list and not even secondary or tertiary, like way down the line is, is the product that they actually are asking people to buy.

• 1:29:00Ryan Holiday?

  Right, right, because they're just, then they're selling their email list to other people's email list. It's like a total, it's a Ponzi scheme, basically.

• 1:29:07Rich Roll?

  Exactly.

• 1:29:07Ryan Holiday?

  And so I, I definitely hate that. And I think, you know, my goal is to write books that will last. And I want to, I want to market them to my, the best of my ability now. But I'd like for a decade from now for them to still be selling. And that's the sort of timeline that I'm thinking about. I'm not thinking, I don't see the internet as this cash grab where I can make a lot of money with some crappy online course right now.

• 1:29:30Rich Roll?

  Thing.

• 1:29:30Ryan Holiday?

  Yeah, and I, and one of the reasons that, like, I think it's really interesting, because you know a lot of these people, that they talk about how much money they make with these courses and all these things.

• 1:29:38Rich Roll?

  They're making crazy money, crazy money.

• 1:29:40Ryan Holiday?

  But then what are they doing? All of them want to write New York Times bestselling books.

• 1:29:44Rich Roll?

  Right, well, and then they, but, but then they get, they, they write a huge check to results source. They buy their own book back, then they get on the New York Times bestseller list and like, the, you know, the, the unassuming consumer doesn't know the difference. They don't realize that they've just gamed this entire thing. Like, as somebody who is an expert in gaming the system, which you are, uh, you know, and, and like, reading, you know, reading, trust me, I'm lying, I learned so much and it was fascinating. But as somebody who's kind of standing by on the sidelines, I, I look at that and I go, there's a, there's a, it's a, you know, on the one hand, I'm jealous.

• 1:30:17Ryan Holiday?

  Sure.

• 1:30:18Rich Roll?

  I'd like to have a book on the New York Times bestseller list, but I'm not gonna, I'm not gonna, I'm not gonna write a check to results. I'm not gonna do that. Like, I'm interested in longevity.

• 1:30:26Ryan Holiday?

  Totally.

• 1:30:26Rich Roll?

  And, and ultimately, the most important thing to me, above anything else, is credibility. And authenticity, authenticity. And the minute you start to do that, you are undermining that.

• 1:30:37Ryan Holiday?

  That, that's sort of my point, though, is like, it, to me, it's very telling, with these people who are making all these, all this money. All they really want is credibility and influence. Like, that's all they actually want.

• 1:30:48Rich Roll?

  But every action they're taking is undermining that.

• 1:30:49Ryan Holiday?

  Right, right. No, that's why I'm, it's like, Like, they think that they had to make millions of dollars selling scammy products to then pay to get on the New York Times bestseller list, when really, they could have just sat down and wrote an actually good book.

• 1:31:02Rich Roll?

  Spent all that energy on doing something good.

• 1:31:04Ryan Holiday?

  Right, no, it's, it's, it's, it's, it's a crazy model, and, and I,

• 1:31:10Rich Roll?

  And I think this is another instance in where Tim Ferriss is misunderstood, because he's so masterful at, at being transparent with like, all the tactics that he used to make his books successful.

• 1:31:20Ryan Holiday?

  Yeah.

• 1:31:20Rich Roll?

  And that gets all the attention. What doesn't get the attention is how much time and work he put into creating books that people actually enjoy and find useful.

• 1:31:28Ryan Holiday?

  Well, like, because I'm thinking about this for Project Now, maybe the metaphor I've been kicking around is like, look, it takes the same amount of time to get, or energy to get a plane up in the air as it does like, a glider, right? But like, if it doesn't have an engine, what's the point? Right? Like, if, if you're gonna do all this work and all this energy to make something that doesn't last, why? Like, why would you do, like, these people are like, "Oh, my book is a business card, that's why I'm doing it." Well, it's like, your business card has an expiration date on it, like, that doesn't make very much sense. Like, so, I'm trying to, like, people, For Our Work Week, people think was this expertly marketed book, and, and it was, but, it's also still in hardcover, like, a million and a half copies later.

• 1:32:10Rich Roll?

  Right, it's still selling because it's a good book.

• 1:32:12Ryan Holiday?

  Right, it, he didn't market his way to 1,500 reviews on Amazon. He marketed his way to 200 reviews on Amazon in the first year. That's market, marketing is, marketing is the catalyst that kickstarts a process, and I've just seen too many people, especially in the fitness space, have huge lists, write crappy books, get immediate success, and then fall off the face of the planet, and I, I just don't understand the point. It's not, I don't, I mean, look, I'll take their money, but like, I don't understand the point of that process. It does, doesn't, it's not worth it.

• 1:32:49Rich Roll?

  Ultimately, yeah, it's, it's, it's just a short-term thing, you know? It's never gonna, it's never gonna be sustainable in the long run. And so, I'm always watching and saying, seeing how these things are playing out over time. And for me, like, I've kind of, you know, I got into this without any understanding of marketing whatsoever.

• 1:33:05Ryan Holiday?

  Sure.

• 1:33:05Rich Roll?

  And I kind of, you know, engaged the, like, I love podcasting, right? I didn't do it because it's a lead generator for something else that I'm doing it. I love it because it's the greatest scam in the world to get people like you to drive over to my house and sit down and talk to me for two hours. So now I know you.

• 1:33:21Ryan Holiday?

  Right.

• 1:33:21Rich Roll?

  It's amazing. And the fact that other people will enjoy that is great, but I just love the medium. I'm trying to create the best product that I can, and I'm not looking for a payday. But I trust that if I'm putting great content out, whether it's through a book or a podcast or whatever it is, a blog post, that that ultimately will translate later on into something that perhaps I can't predict right now. But I, but that has been proven to be the case for me time and time again. So I'm playing, you know, I'm playing the long-term view on the whole thing.

• 1:33:48Ryan Holiday?

  Yeah, like.

• 1:33:49Rich Roll?

  But I'm not worried about my list. Maybe I should worry, you know, like, I don't think about those kinds of things.

• 1:33:53Ryan Holiday?

  Like, when I was starting, I would hate that people go like, all you gotta do is write a great book. Like, I feel that's very disingenuous, because it's more complicated than that. But it is the most critical step. So like, the best analogy that I've heard is someone, they were like, it's a marathon and a sprint. And you've gotta, you've gotta understand that. And I think the infomarketer people are really great at sprinting. And then if they stayed as sprinters, it's fine. But then they also try to create these other products. Or they have, they tell you that what's really important is building something to last. And I don't think in five years, half these podcasts are gonna be here, half these blogs are gonna be here. They just won't, because what do they, it's like, it's like you're reading it and you're like, is this a riddle?

• 1:34:38Ryan Holiday?

  Like, is this a poem? Like, where, there's that saying, um, there's no there there. Like, when are you gonna tell me something that's real intangible?

• 1:34:48Rich Roll?

  Right.

• 1:34:48Ryan Holiday?

  Instead of, it's like, I already signed up for your list. What are you selling me here? Like, I just want some facts. And they can't do it.

• 1:34:56Rich Roll?

  Right, you're always like, almost at the, at, almost there, but then there's one more thing that you have to do and.

• 1:35:02Ryan Holiday?

  It's, you're almost there, and then you gotta do a webinar. Or you're almost there, and then, then you gotta, then you gotta come to their meetup or buy their course or do their stuff. And it's like. I and and I I'm sure I'm sure you've talked to those same people that like you can make a million dollars a year if you created a course. And when we talked about, you know, um, the hardest thing in the world to do is to turn down money. It takes a lot of discipline to say, I know, but I don't like that. And so I'm not going to do it.

• 1:35:32Rich Roll?

  Yeah, I've said no to a lot of that kind of stuff. And I would say almost every single day. I get an email from somebody about how they're creating some online summit. All they want to do is they want to they want to eat. They want to interview me on Skype for thirty to forty five minutes. And I'll be joined by all these other luminaries. They list a bunch of names and then they say, all you have to do.

• 1:35:51Ryan Holiday?

  Promote it to your list.

• 1:35:52Rich Roll?

  Is is send four emails to your list and post it on Facebook fifty. I'm like.

• 1:35:56Ryan Holiday?

  And then you'll get a commission from their thing. Right.

• 1:35:59Rich Roll?

  Or even if it's free, because there I go there. There's nothing to this. They're just trying to build their own email list on the shoulders of other people. I'm like, I don't want to participate in that.

• 1:36:07Ryan Holiday?

  Right, like.

• 1:36:08Rich Roll?

  It's not about the wellness summit. It's about building their email list.

• 1:36:12Ryan Holiday?

  No, when I got here, I got a letter from my speaking agent because I'd I'd forwarded him something and he was like, no, this is another online summit. And he was like, you don't want to do. You probably don't want to do this. I was like, you're right. And and it's like, it seems weird, but it's like, I would rather take less money upfront. For you to say like, we're paying you X amount of money to come to this place to give this talk to this audience. And then you do your job and we'll do our job and then that's it. But these it there. I think I think it's a huge sort of bubble Ponzi scheme-esque thing where. If people stopped believing that they could do the same thing themselves, like if people stopped believing. That like, oh, I could also create my own huge email list one day. I think a whole the whole thing would collapse.

• 1:36:56Rich Roll?

  Mm hmm. Well, it's gonna be interesting to watch how it plays out and work every time. So.

• 1:37:00Ryan Holiday?

  Yeah.

• 1:37:01Rich Roll?

  All right. Well, if you were me, like, what what what would you recommend that I do? Like, what am I not doing well? Where could I improve? What am I? What? You know, like as a as a put on your marketing hat?

• 1:37:14Ryan Holiday?

  I mean, I would write another book. I think you should write another book. Um, I might update your, your first book and do a second round on that.

• 1:37:22Rich Roll?

  Yeah. I mean, when I look at it now, there's so many things I would change.

• 1:37:25Ryan Holiday?

  Yeah. And, and like, I, I would be, I would be looking at it as like, this is a classic timeless book. So how, now that I know, now that you've made it over the gap, like, how old is that book? Five years?

• 1:37:35Rich Roll?

  Two thousand twelve.

• 1:37:36Ryan Holiday?

  Okay. So, yeah. So now that you've made it over, you, you're not, you're now a backlist title. How can you ensure its success as a backlist title? I think that would be a big thing. Um, I don't know. I don't, I, I think it, I would, I would push back and say like, what are, what do you not have that you wish you had? And then I would talk about what you should do. Cause I think that's the hard part. It's like, um, you know, people, like, I think about this a lot with these infomarketer people. I'm like, oh, I heard so and so is making like six figures a month doing X, Y, and Z. And then I'm like, but I don't want to do X, Y, and Z. And also I, it, this sounds weird, but it's like, I'm not like,

• 1:38:17Ryan Holiday?

  I don't wake up every day and go like, I need more money. Like I need more money, you know? And money is not what is important to me and it's not what gets me excited. And so I'm like, I have, you have to be able to go like, they're running their race and I'm running my race. And all that matters are individual times. Um, we, if we're comparing each other, we're gonna be, you're gonna totally throw each other off. So I think that's, I always-

• 1:38:43Rich Roll?

  I'm clear on that. I'm clear on that. Like, I don't get caught up in other people's traps or-

• 1:38:47Ryan Holiday?

  No, I just mean like, it would be impossible to ask, answer your question without actually, like, like when I do a session with an author, I'm like, what are your goal? Are your goals to sell a lot of copies? Is your goal to be on the bestseller list? Or is your goal to make a lot of money? Cause you think those goals are the same, but they're not.

• 1:39:02Rich Roll?

  Right.

• 1:39:03Ryan Holiday?

  They're very fundamentally different. And so I would like, you know, what is, you know, it would be like, what, what do you feel like doing? Or what do you feel like it would be really nice to have or do? And then I'm sure there's tons of creative things to, to do that. Like, yeah, I think that would be, I think that would be the place to start.

• 1:39:24Rich Roll?

  Right. Well, the new book is, another book is definitely happening.

• 1:39:29Ryan Holiday?

  That's the best, the best marketing thing in the world is to write another book.

• 1:39:32Rich Roll?

  I'm wrestling with what that's gonna be, but.

• 1:39:36Ryan Holiday?

  Yeah.

• 1:39:36Rich Roll?

  And I just, and I just, I just violated your principle.

• 1:39:40Ryan Holiday?

  No, no, no, no.

• 1:39:41Rich Roll?

  But it's not a mystery that I was.

• 1:39:42Ryan Holiday?

  Have you sold it yet?

• 1:39:43Rich Roll?

  I'm gonna write another book. No, no. Uh-uh. No, no.

• 1:39:45Ryan Holiday?

  Well, then, and, and it's weird to think that the best marketing you will do for that book will be in thinking about what it is and who it's for and how you're gonna do it. Like, you're gonna make all the critical writing, just all the critical marketing decisions before you write, and then write about the time you finish writing, and then everything else is tactical.

• 1:40:04Rich Roll?

  Hmm.

• 1:40:05Ryan Holiday?

  Everything else is how do you best utilize your list, you know? Do you do an event at this store or that store, you know? Um, what, what are the bonuses you wanna, all that stuff is tactical. And it's all determined by what book you write.

• 1:40:20Rich Roll?

  Right.

• 1:40:20Ryan Holiday?

  And who it's for.

• 1:40:22Rich Roll?

  Right. But in, in the, in the, uh, Principles of Stoicism, it's just about writing the best book that I can and engaging in the process of, of that on a daily basis.

• 1:40:33Ryan Holiday?

  Yeah, and, and stripping out, stripping out the, the vanity or the selfishness or the insecurities that are inherent. Like, everyone wants to write it. It's like, like, why do you have these artists who have sold millions and millions of copies? And then they're miserable because like, some shitty critic at Rolling Stone thinks they suck. It's like, you wouldn't care about that guy's opinion at a party, but because he wrote about it in a magazine,

• 1:41:00Rich Roll?

  Mm-hmm.

• 1:41:01Ryan Holiday?

  you're like, ready to invalidate like, years of your work.

• 1:41:04Rich Roll?

  Mm-hmm. Yeah, well, it takes, it, it takes a strong sense of self to be able to rise above all of that.

• 1:41:11Ryan Holiday?

  Yeah. Not too strong, because you gotta be, you have to actually be available to hear from your wife when she's like, Rich, like, this is, you're not there, you're not done yet. Like, you gotta go back to the drawing or whatever.

• 1:41:23Rich Roll?

  Right. Well, I mean, that brings up the importance of mentors and, and, you know, to the extent that you need to kind of covet your idea and, and be, you know, somewhat private about it, it also is important to have people in your life that give you objective feedback and tell you the way that it is.

• 1:41:38Ryan Holiday?

  Yeah, it's not about going off into a cave and coming back with

• 1:41:42Rich Roll?

  Something that's genius.

• 1:41:43Ryan Holiday?

  your masterpiece.

• 1:41:44Rich Roll?

  Yeah, yeah.

• 1:41:45Ryan Holiday?

  Um, and then.

• 1:41:46Rich Roll?

  And that's the illusion of, of, of writing, I think, for a lot of people.

• 1:41:49Ryan Holiday?

  Yeah, like, one of my least favorite creative sayings is that one from Hemingway, where he says, like, "Writing isn't hard, it's sitting down at a typewriter and bleeding." It's like, that's not what writing is at fucking all. And, and considering the fact that we can look at your meticulously edited drafts of your manuscripts, we know that you didn't believe that either. But if you're a 22-year-old MFA student, and you're struggling to come up with your idea for a book, sitting down and letting it bleed, you know, sounds, sounds like what it should be.

• 1:42:25Rich Roll?

  Right, right.

• 1:42:28Rich Roll?

  All right, well, I think this is a good place to wrap it up, but I want to close it down with like, um, one last question, which is, you know, if somebody's listening to this and they're, they're stuck in a cubicle somewhere, and they're just, they're hating their job, and they're hating their life, and, and perhaps they have a spark or, or some inkling of a better way to live.

• 1:42:46Ryan Holiday?

  Yeah.

• 1:42:47Rich Roll?

  You know, what are some tips or tools that could be utilized to start to be more expressive of that passion?

• 1:42:57Ryan Holiday?

  Um, I don't know if this totally answers your question, but I'm sure you, in some of the 12-step stuff I've done, I've seen this too, where like, uh, the idea of like, a conditional future is very dangerous, right? So it's like, if this happens, then I'll be happy, right? And so I think when people are like, "I hate my job, and so I want to do something different", they think about like, they're like, they think about what it needs to be for them to like, quit their job, or, or whatever, and they don't go like, "Look, it's not going to magically happen. You have to start like, right now, with something really, really small." Like, it, another train is not going to pull up alongside you, and you just jump off yours and get on that one. It's, you gotta start. And so I think, I think it, it's like, people, people are like, "Oh, I want to be a writer",

• 1:43:42Ryan Holiday?

  and I was like, "Well, what do you have to write about? Like, what are you doing that's interesting, that would make for good writing?" And it's actually a good thing that you have a job, because now you can fund that.

• 1:43:51Rich Roll?

  Right.

• 1:43:51Ryan Holiday?

  And so I, I think the big thing for like, creative people, or like, people who want to do something, it's like, you don't need to come up with a genius business idea that is immediately self-sufficient, um, blah, blah, blah. Um, Ramit Sethi, who I actually think is, is, is in the space we were talking about earlier, but actually really great, he's like, Your goal should be like, I want to make a thousand bucks a month on the side with my passion project. He's like, that's very attainable. And once you make it to a thousand bucks, then you can decide whether it's, you can see very clearly whether it's scalable to becoming a sort of full-time income replacement or whatever. But it doesn't, it's not about inventing Facebook in your garage. It's about, I had this fun idea. It's you deciding, I'm gonna

• 1:44:36Ryan Holiday?

  start a blog, or like, hey, it would be cool if I did a podcast. It's not like, uh, let's pull the emergency brake, let's stop everything, let's burn all the bridges behind us, and then, uh, have our flash of creative inspiration and immediate success and all these things.

• 1:44:53Rich Roll?

  Well, that's not sexy.

• 1:44:54Ryan Holiday?

  Of course.

• 1:44:55Rich Roll?

  You know what I mean?

• 1:44:55Ryan Holiday?

  Right. That doesn't make for a good movie.

• 1:44:56Rich Roll?

  But that's the truth. It's sort of, yeah, it's like, there's this idea that we hold on to, that it is gonna be, you know, that it has to be this big dramatic thing. But the truth is, everybody has free time, no matter what your job is, I don't care what your circumstances are. If you sit down and you plot out how you spend your time in fifteen-minute increments throughout the day, you will be amazed at how much time you waste, or you'll be able to identify places where you could create efficiencies. And then what are you gonna do with that free time? Are you gonna watch Dancing with the Stars and spend an hour on Facebook? Or are you gonna put some thought into how you perhaps could, you know, take a step in a different direction? And you don't have to explode your life to do that. It can work in tandem with that life. And I think, then you start to just incrementally,

• 1:45:40Rich Roll?

  on a persistent basis, put more and more energy into that, and it will lead you into a different direction that will create a decision tree that, you know, will then inform.

• 1:45:49Ryan Holiday?

  Like, I really love the concept in the startup world of like, a minimum viable product, right? It's like, you don't have to create, like, it's not like, I had this idea, so then I got a lawyer to copyright it, and then I did this, and then I did that. It's like, No, you start with a landing page and you see if anyone cares like or or like, oh, you want to write a book? Why don't you write a blog post first and see if anyone reads it?

• 1:46:11Rich Roll?

  Right.

• 1:46:11Ryan Holiday?

  You know, like, don't, don't front load.

• 1:46:13Rich Roll?

  And even if no one does, who cares? Write another one. Like, it goes back to embracing the process. If that's what you love doing, trust in that and just make it better the next time. Like Casey would say, make a crappy movie.

• 1:46:24Ryan Holiday?

  Right. Don't front load hundreds of hours of work. Um, because like, uh, there's that great, I love this quote from, um, Ira Glass. He talks about the, there's this sort of gap between taste and talent when you first start. And he's like, what, what happens is you have really great taste. That's what makes you good. But your stuff sucks. And it's the idea that that gap is like so hard for people.

• 1:46:46Rich Roll?

  Uh huh.

• 1:46:46Ryan Holiday?

  And so it's like, don't go write your first crappy novel before you've interacted with a public or readership at all, because you're going to be crushed when, when with, by the indifference. But if you write a blog post and 25 people read it, you're like, 25 people read my blog post. I'm gonna write another one. And then the next one does 30, and then the next one does 50, and it goes from there. That's how you get started. It's those little decisions that change your life. Um, it, it was the idea that, you know, I wanted to recommend books to people that built my email list that helped me sell my first book. And this, this was an idea that I ran by my friend. And he was like, that's a terrible idea. You shouldn't do it. And I was like, well, it doesn't cost anything. So like, I'm gonna do it anyway.

• 1:47:26Rich Roll?

  What does the opportunity cost of that?

• 1:47:28Ryan Holiday?

  Right. It was nothing.

• 1:47:29Rich Roll?

  Right.

• 1:47:29Ryan Holiday?

  And, uh, so you, so start small and be grateful for the, the success rather than like, have these huge expectations that set you up to, to be discouraged when you really can't afford to be discouraged.

• 1:47:46Rich Roll?

  Hmm. Awesome, man.

• 1:47:49Ryan Holiday?

  This is really great. I had a great time.

• 1:47:50Rich Roll?

  Thanks for doing it.

• 1:47:51Ryan Holiday?

  Yeah.

• 1:47:52Rich Roll?

  I think we did it.

• 1:47:52Ryan Holiday?

  I'm exhausted, but.

• 1:47:53Rich Roll?

  Are you?

• 1:47:54Ryan Holiday?

  Yeah. Now it's go taco roast the day.

• 1:47:56Rich Roll?

  Come on. No, that was great, man. Thank you so much. Awesome. It was great to have you. It was so insightful. I really appreciate it. If you're digging on Ryan, the best way to connect with him is ryanholiday.net, which is his website, where he shares his thoughts. Subscribe to his monthly list of books that he recommends and watch your life improve. And you're pretty easy to find online. Yeah, yeah. At Ryan Holiday. And you're still an editor at The Observer, yeah? Yeah, yeah. And you also write for Thought Catalog. Where else do you write for? I'll write anywhere that takes me. Yeah. And when's the new book gonna come out? One will be July 2016 and one will be fall 2016. Do you have a title yet?

• 1:48:40Rich Roll?

  "Ego is the Enemy." I've never told that anywhere. I already have it. Uh oh. Oh, you have it tattooed on you already? I have both. Yeah, that's cool. I like that, man. Now they can't, they can't, they can't force me to change the title now. Not only that, you've set a precedent that every time you write a book, you have to tattoo the title on your body? Well, one of my books is called "Growth Hacker Marketing," so I probably won't be tattooing that anytime soon, but... Do you have "Trust Me, I'm Lying" on your tattoo? No. These are actual phrases that I care about. All right, cool, man. Well, thanks a lot, dude. Yeah, thanks. And hopefully you'll come back and do this again. Anytime. We'll go running. Cool. Awesome, man. Peace. Plants.

• 1:49:23Rich Roll?

  Good guy, right? Interesting guy. Hope you guys enjoyed that. Go ahead, check out his books. "Start with Obstacle is the Way." Read his articles, read his blog. You'll be better for it. Very, very insightful, bright young man, and it was a pleasure talking to him. Let me know what you guys thought of the episode in the comments section on the episode page at richroll.com. For all your plant power needs, go to richroll.com as well. We've got nutrition products. We've got signed copies of Finding Ultra on the Plant Power Way. We have 100% organic cotton garments. We have Julie's meditation program, which is killing it right now. People are really enjoying that. We got tech tees, we got sticker packs, we got temporary tattoos, and we have limited edition art prints. All kinds of cool stuff. Basically...

• 1:50:07Rich Roll?

  All kinds of products to take your health and your life to the next level. We got your bases covered at richroll.com. Keep sending in your questions for future Q and A podcasts to [email protected]. Loving that. And check out my online courses at mindbodygreen.com. The Ultimate Guide to Plant-Based Nutrition and The Art of Living with Purpose. I'm really proud of both of those courses. They're really great. Go to mindbodygreen.com, just click on video courses and you can find out much more information there. So, thanks for all the support of the show, you guys. Keep telling your friends, I love it. Keep sharing it on social media. Really appreciate the support and thank you for using the Amazon banner at richroll.com for all your Amazon purchases. I love it. I'll see you guys in a few days.

• 1:50:52Rich Roll?

  Make it a great week. Catch you on the flip side. Peace. Plants.