Ryan Holiday: Stillness Is The Path To Everything We Want In Life

He's best known for popularizing Stoicism — an ancient philosophical yet highly practical operating system he pioneered to mainstream, modern adoption. In his latest turn, Ryan Holiday expands his lens East. In pursuit of shared wisdom across ancient Buddhist, Muslim, Hindu, Hebrew, Greek, Christian and Epicurean traditions, he discovered one essential truth — that inner peace is essential to a life of purpose, meaning and fulfillment. Ryan calls it stillness — to be steady while the world spins around you. A crucial characteristic of all great leaders, thinkers, artists, athletes and visionaries, it's a practice to transcend the stress of everyday life. An antidote to the distractions of our fast-paced world. And the ultimate path to meaning, contentment, and excellence in a world that needs more of it than ever. For those unfamiliar, Ryan is an autodidact who dropped out of college at 19, maturing into one of the most important thinkers of his generation. Now 32, he is a media strategist, prolific writer and public speaker with six perennial bestselling books to his name, including Ego Is The Enemy,The Obstacle Is The Way, and Conspiracy. Making the digestible case for why slowing down is the secret weapon for charging ahead, Ryan's latest release — aptly titled Stillness Is The Key (hitting bookstores everywhere this week) — is your next must read and read again primer on living your best life. Returning for this third appearance on the podcast (check out RRP #168 and #239), today we explore the essential elements of stillness — and its limitless applications for profound personal self-improvement. Want to avoid distractions? Develop greater insight? Unlock creativity? Improve your decision making? Better your parenting skills? Enhance athletic performance? The incredible power and practicality of cultivating placidity in our increasingly turbulent, tumultuous, reactive, distraction monopolized lives simply cannot be overstated. Stillness is the key. You can watch it all go down on YouTube. I have great fondness for this human. I absolutely love this exchange. And sincerely hope you do as well. Peace + Plants, 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?

  Eating well rarely falls apart because of one big failure. It's the daily question that wears you down. Like, what am I actually gonna make tonight? What's in the fridge? And it's exactly why we built the Plant Power Meal Planner. It's a personalized, plant-based meal planning program that matches you with recipes based on your taste, your allergies, your cooking skills, and how much time you actually have. You build, through this program, a balanced, nutrient-dense plan for your entire household in a few minutes. Then it generates a grocery list for you with one click that plugs right into our delivery partners. All the recipes in the program are built by dietitians with culinary training. Plus, you get your own food coach to help you problem-solve along the way.

• 0:44Rich Roll?

  It's kind of an amazing thing. For listeners of the show, all you special people, we're offering an exclusive $20 off an annual subscription right now. To get it, go to meals.richroll.com, take your quick personalization quiz, and enter promo code RICHROLL20 at checkout.

• 1:05Ryan Holiday?

  What I try to do in the books is apply ancient wisdom to life in a practical way. And I think the idea of stillness, that concept of stillness, it struck me as like, when you remove ego, stillness emerges. You need stillness to overcome these kinds of obstacles. So it was sort of, it's sort of the glue that went unsaid in the other books. And I just kept coming back to this idea. And when you look at really great people, whether they're athletes, or generals, or just like a wise person that you met, or your grandfather, what they all seem to have is that operating on a different plane. And what's interesting is that basically, and this is what inspired the book, is that

• 1:47Ryan Holiday?

  like, basically, any and all of the ancient schools talk about that idea, that concept of stillness, in their own way, as the sort of the end goal of what we're doing.

• 2:01Rich Roll?

  That's Ryan Holiday, this week, on the Rich Roll Podcast.

• 2:16Rich Roll?

  The Rich Roll Podcast. How goes it, people? Rich Roll here, your host. This is my podcast. Welcome. Okay, time to get serious because today's guest is a very serious man. You know him, you love him. His name is Ryan Holiday, and today he returns to the podcast for his third appearance. Check out Episodes 168 and 239, if you missed them the first time around, to discuss his brand spanking new book, the latest in this prolific, multiple New York Times bestselling, young man's quickly growing canon of important work. It's called Stillness is the Key. It's your next must-read and read-again, and the focus

• 3:01Rich Roll?

  of today's conversation. For those very few unfamiliar, Ryan is an autodidact who dropped out of college at 19 and now, at all of 32, I think, is a media strategist, an author, a public speaker, and I think it's fair to say, one of the most prolific writers and important thinkers of his generation. Ryan is the author of now six, I think, perennial bestselling books. Among them, Ego is the Enemy, The Obstacle is the Way, Perennial Seller, and Conspiracy. Ryan began his already storied career as an apprentice under Robert Greene, the author of The 48 Laws of Power, went on to work with other acclaimed authors

• 3:45Rich Roll?

  like Tim Ferriss, and served as the Director of Marketing for American Apparel, a job that he held at the ripe age of 22. And when he's not writing books or opinion pieces for The Observer or Thought Catalog, Ryan oversees Brass Check, a consultancy firm that advises New York Times bestselling authors like James Altucher, Arianna Huffington, and Tony Robbins, and corporate clients that include Google, CreativeLive, Complex, and Refinery29. I have a great fondness for this human, and a few more things I want to say about him before a conversation I think will profoundly impact how you think and feel about mindfulness.

• 4:33Rich Roll?

  Okay, Ryan. So Ryan is perhaps best known for his affinity for and his popularization of the Stoics, translating and contextualizing this treasure trove of ancient wisdom and philosophy, and then rendering it highly practical and practicable for a modern audience. And along the way, he's won fans from all kinds of people, the next generation of professional athletes and coaches and tech CEOs and even high-ranking politicians. But in this latest book, Stillness is the Key, Ryan begins to stretch beyond

• 5:13Rich Roll?

  the perimeter of Stoicism and, for the first time, I believe, begins to weave in an eastern perspective, insights derived primarily from Buddhism, to make a digestible case for why, as he puts it, slowing down is the secret weapon for charging ahead. How does one avoid distraction? Stillness. How does one develop great insight? Stillness. How does one throw a great pitch, write a great book, parent a healthy child? Stillness, stillness, stillness. So that's what this is about, the incredible power and practicality of placidity

• 5:53Rich Roll?

  in our increasingly turbulent, tumultuous, reactive, distraction-monopolized lives. Here's Ryan.

• 6:06Rich Roll?

  Thanks for coming out.

• 6:08Ryan Holiday?

  No, thanks for having me.

• 6:09Rich Roll?

  I feel like we've done four or five podcasts, and then I realize you've only been on the show once.

• 6:15Ryan Holiday?

  Is it once? I thought it was twice.

• 6:17Rich Roll?

  Maybe you've been...

• 6:17Ryan Holiday?

  I think it was twice.

• 6:18Rich Roll?

  No, you're right. Yeah, I think it has been twice. But it does feel like I've, I don't know, we've talked a lot off the microphone, so...

• 6:25Ryan Holiday?

  Which is like the opposite I have with most people. I feel like I only get to see them during podcasts, and it's the only time we talk for like three hours in a row.

• 6:33Rich Roll?

  Your entire relationship with somebody is based on recording podcasts, which is increasingly my relationship with my wife.

• 6:41Ryan Holiday?

  Well, I like, that's what I liked about the one that you did with your dad. I was like, I've never had that conversation with my dad because you never would, you would do it.

• 6:48Rich Roll?

  You'd never do it. It's, it's something that, that we probably think a lot about like, oh, when's that day going to come? And I'm going to sit down. I'm going to, you know, we're going to have a Scotch and, you know, talk about your life. And that moment never really arises. And it had occurred to me that I wanted to do that. And I wanted, there's something about putting a microphone in somebody that, in front of somebody that creates a formality and a structure. Yeah. That kind of allows that to transpire because it forces the person to actually think about what they're going to say with the idea that I would never, probably never share it. Yeah. But then when he wrote the book, and then it was like, okay, we can do this. Yeah. Yeah. Yeah. And I appreciate all the support and the, and the help that you've lent to him and his book. It's

• 7:31Ryan Holiday?

  I don't know. I mean, I told you I would have done it anyway, because I thought it was a really good book and I thought it was important.

• 7:36Rich Roll?

  Yeah. It's funny. You told me the story of meeting my dad when he showed up. One of your, one of your book signing things and he just like rolled right up to you right before you were supposed to speak, right?

• 7:48Ryan Holiday?

  I don't, I don't know if it was right before or right after, but it was, I remember we texted about it. You and I. I, I recognize some of my dad and your dad. And yeah, it was funny.

• 8:01Rich Roll?

  Yeah. Well, the occasion of this podcast is, is your new book, which we're going to get into in a minute, which I loved. I think it's fantastic. I really, this is like right in my wheelhouse. Like, I just love it. But before we get into that, like, I wanted to spend at least a couple of minutes talking about this other part of, of what you do. I mean, you're in LA because you were down speaking with the Rams, right? And this is something that you've been doing more and more of. It seems like every week you're at another major league sports franchise.

• 8:31Ryan Holiday?

  Well, this is an unusual set of two weeks, but yes, last week I was with the Browns and I got to speak to the team and, and that was, and I spent a couple of days with them. That was very cool. They, I was most excited. They let me swim in the team lap pool. Wow. And so, and it's, it's at field level. So you can watch, you're, you're basically looking at the ankles of the players going through walkthroughs in practice as you're swimming.

• 8:58Rich Roll?

  Right.

• 8:59Ryan Holiday?

  So, and, and they only let me use the pool when the players were practicing because then they wouldn't be. There. So that was really cool. And then I happen to know the GM of the Rams and he invited me out. And so I spoke to the coaches yesterday and today.

• 9:16Rich Roll?

  And what is that? What's that like? Like when you're talking to the, do you talk to the players as well? Or is it mainly?

• 9:20Ryan Holiday?

  For the Rams, I didn't. I've spoken to different teams like it before. It's a very weird audience. The weirdest audience was so in March, I spoke at the NFL owners meeting, which was probably the most unusual audience that I'll ever speak to. I mean, aside from maybe addressing the UN, like, when would you have?

• 9:43Rich Roll?

  This aggregation of billionaires?

• 9:45Ryan Holiday?

  Yeah, I mean, so it's a minimum of 32 billionaires. And then it was all the head coaches and all of the team presidents and all the GMs. And so it was just, it's just a surreal audience. I mean, it's like, it's humbling to be there. But then you're just like, I think what strikes me is like, I'm talking to these people about ancient philosophy. This is like, I think that's so cool. And it's also so absurd at the same time.

• 10:10Rich Roll?

  Well, I mean, certainly when you sat down to, you know, write these books, this series of books, you could not have predicted or imagined that it would have been embraced in this, you know, sort of subculture to the extent that it has.

• 10:23Ryan Holiday?

  I mean, it would have been delusional is the only word. But it does make sense. Like, there's a bunch of Stoics who were athletes. I think what I try to do in the books is apply ancient wisdom to life in a practical way. And I think, I think I would like to think I'm not just like, hey, here's how you get through the day. But I want to say like, hey, what is, what are the really smart people throughout history figured out about being elite at whatever you do, whether that's being elite as a human being or a parent or, you know, an athlete or a leader or whatever. But it's just, it's just really cool. I like, it's just, I just really like, I like talking to all different audiences, but it's certainly much more interesting to address a sports team that you've watched

• 11:07Ryan Holiday?

  on television that it, that it's sort of struggling, bumping up against the limits of like, human performance.

• 11:12Rich Roll?

  Right.

• 11:13Ryan Holiday?

  Than it is to talk to an insurance company. Not that I don't like talking to the insurance company, but there's just.

• 11:21Ryan Holiday?

  There's a purity to sports that I'm interested in because like, like when you, I don't know, just all the cliches that if a normal person said, you'd be like, that's lame. An athlete can stay in a locker room after a game and it has this significant.

• 11:38Rich Roll?

  Inspirational.

• 11:39Ryan Holiday?

  But it is like, they really mean it. They're not like bullshitting, you know, like they really are. They really do speak in these sort of like cliches and, and epigrams because it's, and I talk a little bit about this in the book, but you know, Yogi Berra had that line like it's impossible to think and hit at the same time.

• 11:58Rich Roll?

  Right.

• 11:58Ryan Holiday?

  So at sports, because your body's doing most of the work, you have to simplify the mental, it's like you have to simmer the sauce down to its absolute essence.

• 12:07Rich Roll?

  Uh huh.

• 12:08Ryan Holiday?

  And so it's just so simple and straightforward and there's no like irony or bullshit or, you know, posturing in sports is just there.

• 12:17Rich Roll?

  Well, I think there's a difference between a, a group of executives who all want to perform, but fundamentally it's a job, right?

• 12:26Ryan Holiday?

  Yes.

• 12:26Rich Roll?

  That's different from an athlete, that it's their job as well, but the, the level of receptivity to finding that extra edge to game performance, I think is probably much more heightened in that community.

• 12:40Ryan Holiday?

  Yeah. And you know, hearing you say that, I would say the only other group where you're like, these are all the best people in the world at what they do and they're on the same team would be like the military. Like there would never be, there's no audience, there's no like, hey, these are the 30 best writers in the world. And somehow they're on the same team.

• 13:00Rich Roll?

  Uh huh.

• 13:00Ryan Holiday?

  Sitting in the same room and you can address them. Do you know what I mean? Cause everything else is like one-on-one combat, like the rest of the, the world, like my books have spread through sports because like, like a guy at the, at the thing I talked to today, it was telling me he'd read the book and I said, how did you hear about it? And he told him, This is not like a high level guy. This is just a guy. He's like, oh, the GM of this other NFL team told me I should read it.

• 13:28Rich Roll?

  Right.

• 13:29Ryan Holiday?

  The CEO of Google does not recommend books to anyone, let alone like the people at rival companies.

• 13:35Rich Roll?

  Uh huh.

• 13:36Ryan Holiday?

  And so there's just a, it's just a unique thing where you're like, all these people are like on the same team, trying to get better together. There's just a coolness that I don't, there's no other audience where you get to do that.

• 13:47Rich Roll?

  Yeah. So as somebody who wrote a book called Ego is the Enemy, I mean, that's gotta be a challenge to keep your ego in check when somebody says something like that to you.

• 13:56Ryan Holiday?

  Yeah.

• 13:57Rich Roll?

  You know, cause that's, that's heavy, man.

• 14:00Ryan Holiday?

  Yeah. I mean, I, what I, what I try to remind myself is, is, uh, none of these people care. Like they're like, you're just like, you're talking to the players and they're just like, if he gives me something I can use, I'll use him and then I'll immediately forget who he is. Like.

• 14:17Rich Roll?

  And next week, somebody else is coming in.

• 14:19Ryan Holiday?

  Yeah. Yeah, exactly. And, and it's also good to just remind yourself of like, success in our field is like the rookie minimum contract in the NFL.

• 14:30Rich Roll?

  Right.

• 14:30Ryan Holiday?

  Do you know what I like? Like you're just like, oh, this is, it's humbling just to be, you're like, I'm in your world, but I'm not of your world.

• 14:38Rich Roll?

  Right.

• 14:38Ryan Holiday?

  So I, that's what I try to focus on.

• 14:40Rich Roll?

  What is the most surreal experience that you've had kind of navigating that terrain?

• 14:45Ryan Holiday?

  That's a good question. I mean, it, it's like you'll get recognized, like every once in a while get recognized, like in, and it's like, I'm, this is supposed to be going the other direction.

• 14:53Rich Roll?

  Uh huh.

• 14:54Ryan Holiday?

  You know what I mean? Like, uh, that's, that's, uh, that's weird. Um, I don't know. It, it, I think the, the weirdest thing about the sports stuff is every once in a while, I'll just get like an email from a head coach or GM or something. And you're just like,

• 15:13Ryan Holiday?

  Even at that level, these are just normal people reading books and then shooting a note to the author because they like them. Like, it's still pretty normal. I don't, that's, that's the surreal experience. You just wake up and you're like, huh, what? Is that, that from who I think that is from? Like, and I just wanted to like chat, you know?

• 15:33Ryan Holiday?

  Yeah, I don't know.

• 15:34Rich Roll?

  It's cool. Well, in addition to, to athletes and sports franchises, I mean, your, your writing has been embraced by Silicon Valley, like these other subcultures that are really steeped in, in, you know, that, that like fine edge of performance. And, and generally just how to live a more meaningful life and do it in a, you know, in a grounded, strategic and fundamentally rewarding way.

• 15:59Ryan Holiday?

  I hope so.

• 16:00Rich Roll?

  Yeah.

• 16:00Ryan Holiday?

  I hope so.

• 16:01Rich Roll?

  So stillness is the evolution of this process. And I, and I say evolution very mindfully. Like, I think it really is, in certain ways, it's synthesis of your other books. And it's also, you know, a very natural next chapter. And certainly, your most spiritual book.

• 16:22Ryan Holiday?

  Yes.

• 16:23Rich Roll?

  So I'm interested in how you arrived at the decision to tackle this subject matter and why this became your next book.

• 16:32Ryan Holiday?

  Yeah, I mean, I think stillness, the idea of stillness, not, I'm not referring to the book, but the idea of that, that concept of stillness, it struck me as like, when you remove ego, stillness emerges. You need stillness to overcome these kinds of obstacles. So it was sort of, it's sort of the glue that went unsaid in the other books. And, and so I was, I just kept coming back to this idea. And when you look at really great people, whether they're athletes, or generals, or just like a wise person that you met, or your grandfather, what they all seem to have is that I just am a, because I'm not a still person. I'm like a high energy person. You probably hear it through the microphone. Like I move my arms a lot, you know?

• 17:15Ryan Holiday?

  I'm like that kind of person. So when I meet someone, you're just like, whoa, you're just like operating on a different plane.

• 17:21Rich Roll?

  Yeah, that like unflappable, calm, you know, groundedness. It almost seems archaic because it is so rare that you now meet somebody of that kind of stature.

• 17:33Ryan Holiday?

  Yes. And what's interesting is that basically, and this is what inspired the book, is that like, basically, any and all of the ancient schools have their, are talk about that idea in their own way as the sort of like the end goal of what we're doing.

• 17:53Rich Roll?

  Yeah, it's a consistent thread that you'll find in every philosophy and every religion fundamentally, which is something that that you explore.

• 18:03Ryan Holiday?

  Like Stoicism and Epicureanism are supposed to be opposite philosophies. And yet like Stoics talk about apotheia and the Epicureans talk about ataraxia.

• 18:13Rich Roll?

  Yeah, I wrote down all those words.

• 18:14Ryan Holiday?

  And I can only pronounce a few of them myself.

• 18:16Rich Roll?

  Aslama, Hishtavat?

• 18:20Ryan Holiday?

  Yes.

• 18:21Rich Roll?

  Samatvan.

• 18:22Ryan Holiday?

  I just went through all of them to record the audio, but I was just in that, those two, it's like, wait, they have, these are opposite philosophies. They have the same idea in basically very similar words. You're just like, whoa, how does that? And then you realize, oh, that's just what we're all working towards. Everybody is trying. Everyone wants to be calmer and more in control and less like heart beating out of their chest at the whim of their emotions or insecurities and, and, and that we need it not only at like the personal level, but also we know that's where our best like professional work comes from. And so I was just fascinated with that. And it's also something I have no natural inclination towards.

• 19:07Ryan Holiday?

  So I try to, I also try to write.

• 19:11Ryan Holiday?

  For what I'm reaching towards. I wasn't writing ego is the enemy because I don't have an ego.

• 19:16Rich Roll?

  Right.

• 19:16Ryan Holiday?

  The opposite of that.

• 19:17Rich Roll?

  And, and again, you make this conscious decision to not really inject your own personal narrative into the narrative of the book. I mean, you have the, the epilogue at the end where you tell a little story, but other than that, you really remove yourself from it.

• 19:31Ryan Holiday?

  Yeah, my regret, my editor disagrees, but my regret on ego is that it'd be like that I, that I'm even in that book. I would rather not be.

• 19:39Rich Roll?

  You don't want to be there.

• 19:41Ryan Holiday?

  Yeah, I don't want to be there at all.

• 19:43Rich Roll?

  What is that?

• 19:44Ryan Holiday?

  I don't know. I don't know.

• 19:45Rich Roll?

  I think there's a certain timelessness that comes with removing, like it becomes a text.

• 19:50Ryan Holiday?

  Yes.

• 19:50Rich Roll?

  That will withstand the test of time, perhaps a little bit better if you take your own.

• 19:54Ryan Holiday?

  That's what I think. I think it helped the book in the short term. And then every year that goes by, it feels a little weirder, even because like that's not where I am. Like it, it feels like it dates it to where I was when I was writing it, which I get. And I've, I've heard wonderful things from people who appreciate that, but I don't know. I just, I'm trying, I, the book, to me, the, I did write the books, but I almost could read them and enjoy them. Because I feel like what I'm doing is channeling and explaining other people and other people's ideas primarily. And I'm just arranging them.

• 20:34Rich Roll?

  And they're all things that are part and parcel of what it means to be a human struggling. So no matter how far down you are, this path, or where you are in your evolution, we all stumble and it's always, it's always going to be relevant to be able to go back to something that you're struggling and find a passage in one of your books that's going to be apropos.

• 20:56Ryan Holiday?

  Yeah. And, and that was another thing I, you asked me, how do you prevent this stuff from going to your head? I, I've realized too, like someone, every once in a while, like, actually this happened when I was at Cleveland. Like one of the coaches showed me his copy of obstacle or no, of ego. And it was literally a hundred percent underlined, like he'd gone through it multiple times, a hundred percent underlined, almost every page, you know, folded. And, and there's a moment where I go, wow, I can't believe I did that. Like, and I was like, because I read books and I do that to books and here's someone doing it back to me. And then I realized. That's actually the same fact. This book is an accumulation of all the things that I underlined in other books. So of course it's filled with underlines. It's not that, it's not like he's underlining these brilliant, original sentences for me. He's underlining

• 21:40Ryan Holiday?

  the quote that I had underlined in another book and then built my book around. Do you know what I mean?

• 21:46Rich Roll?

  Yeah, I understand that. I mean, your, your role, you're very clear in your writing and it makes, you know, these ideas which are, are difficult to grapple with, very digestible, but you're almost beyond the actual prose. Like you're curating a way for people to emotionally connect with these truths by choosing which stories best illustrate them and, and trying to find stories that also will withstand the test of time.

• 22:15Ryan Holiday?

  Yeah. And like, I think some people think like, like I, I was actually a note I get from my editor sometimes where she's like, you know, people don't know who this is. And I'm like, what do you mean? Like I, like I'm referring to them by their first name or something because like I'm so familiar with that work. I just like assume like everyone's heard this story like 30 times.

• 22:33Rich Roll?

  Yeah. Well, this goes back to my theory. I don't know if I've actually told you this, my theory, my Ryan Holiday theory.

• 22:39Ryan Holiday?

  Yeah.

• 22:40Rich Roll?

  Is that you were born out of time.

• 22:41Ryan Holiday?

  Yes.

• 22:42Rich Roll?

  You should have been born, like you're a guy who should have been storming the beaches at Normandy.

• 22:47Ryan Holiday?

  Well, I'm glad that that didn't happen. I'm glad I didn't have to.

• 22:50Rich Roll?

  But you have the sensibility of, of like the great generation. You know what I mean? You're very interested in, in history and you're fascinated by things that like my grandfather was, that are, that are increasingly rare for somebody of your age, which makes you like kind of pleasantly anachronistic.

• 23:09Ryan Holiday?

  Yeah, sure. Do you know, do you know Jordan Harbinger?

• 23:12Rich Roll?

  Yes.

• 23:13Ryan Holiday?

  So I'm gonna pull, I know I'm delaying, but so he, no, this is like how you, uh, this is also how you get, uh, cut down to size, which is always good. So I was telling him about the book or something and he, he, this is what he said, let me find it. It was so good. He said, uh, Uh, I was like, hey, do you want me to send you the new book? And he's like, oh, I think I heard about it. He's like, is that the book that includes famous historical personalities and how they applied Stoic principles to hard times or something like that? And I was like, and he was like being nice, but I was like, oh, like, was that just like a super sick burn of like, like summarizing like my entire career? Cause that's like all my books. You just describe, is that the one where you you take, you tell stories about famous people filled with lots of quotes from other famous people?

• 23:58Ryan Holiday?

  And I was like, yeah, that you're right.

• 24:00Rich Roll?

  That's what I do. But in this book, going back to the evolution, like you can't tackle stillness without dipping your toe in in Eastern philosophy, right? So this is like your first venture in that direction.

• 24:13Ryan Holiday?

  That was much all new for me.

• 24:14Rich Roll?

  Yeah. And, and, you know, in the Venn diagram, there's, there's a lot of overlap in how these, you know, these ideas are synergistic. But what I found interesting is that most books that would tackle this subject matter are either, they're going to fall into two categories. There is going to be new age books, books about how to meditate or about mindfulness from that kind of perspective, or they're going to be very science oriented, like the neurology, you know, the neurology, what's like steeped in all the studies that prove that you should be meditating and all of that. And you really stayed clear of both of those worlds? And I'm wondering whether you felt compelled at times to, you know, bring in like what,

• 24:57Rich Roll?

  you know, Matthew Walker has to say about sleep or, you know, what these, you know, studies are showing about what happens in our brains when we can be still.

• 25:06Ryan Holiday?

  Uh, totally. It was a weird thing. So I like, you have Dan Harris's book Meditation for Fidgety Skeptics, and I love him. I think he's great. But like even that, it's like, even though you're saying it's for fidgety skeptics, it's for people like you or me, I think most people are like, nope. You know what I mean?

• 25:23Rich Roll?

  Like, I don't, I don't even note, does the word meditation even appear once in this book?

• 25:27Ryan Holiday?

  It appears in passing, but on purpose, I never say you should meditate. One, because I don't, I just like can't, can't do it. But I've, I've.

• 25:38Rich Roll?

  You'd rather tell a story about Churchill and how he likes to go on long walks.

• 25:41Ryan Holiday?

  That's, yes. But, but my point is like, I think people go, people are like, I hear that Eastern stuff is really great. But every time I hear about it, they're like telling me to meditate and I can't meditate. I don't meditate. Th- th- this is what I think most people think. So like that's off the table for me. And I think my, what I tried to do in the book is go, there's a whole bunch of really great stuff from the eastern people that you can benefit for well before you have to like just sit quietly with your own thoughts or, or no thoughts.

• 26:13Rich Roll?

  Yeah.

• 26:14Ryan Holiday?

  And, and the other thing is like, I think, like, the truth is, we live in the West. And so I think one of the reasons that the eastern stuff doesn't work for people is that it seems like it's for a totally different world. And so what I wanted to do is go like, how, how can I apply the eastern insights in a Western, um, like, format? So it's like, we learn by stories. We, we tend to learn by personality. Like, I think one of the reasons that eastern stuff is intimidating to people and to me too, is like, I've never heard of any of these names. So I don't know, like, like when someone hears Marcus Aurelius, they're like, oh, that's that cool guy from the movie Gladiator. Like,

• 26:57Ryan Holiday?

  he was the emperor. I want to be king. You know, like, a- and then you hear a thing about Confucius and you're like, what was that? It was like some wandering guy like in a robe. Should I listen to him? Like, and so I wanted to take the insights, but then, which is what I did with, with Stoicism in the first two books. So I want to take these ideas and then illustrate them with stories of people that most people want to be like. So you get the essence of the lesson rather than going like, oh, I'm just supposed to, I'm supposed to abandon the idea of having a self. I'm supposed to get rid of all my possessions because some name I can't pronounce, you know, said it was a good idea. And then like people who wear yoga pants talk about it a lot, you know?

• 27:39Rich Roll?

  Yeah, I get it. No, I get it. But one of the things you succeeded at is making This ancient philosophy, Stoicism, like, cool? Like, people are all about it, like, it's groovy to be a Stoic? And somebody, maybe it's you, maybe it's somebody else, needs to do the same for some of these archetypes from the eastern traditions, because I think with the right storytelling, somebody could very easily accomplish that.

• 28:02Ryan Holiday?

  Yeah.

• 28:03Rich Roll?

  I think we get caught up in the language and these people we don't know and the, and the kind of asceticism of it all.

• 28:08Ryan Holiday?

  Yeah.

• 28:08Rich Roll?

  It just becomes unrelatable. But if you actually read the Bhagavad Gita, like,

• 28:12Ryan Holiday?

  It's awesome.

• 28:12Rich Roll?

  Talk about warriors, these guys are like, total badasses and what they're doing, the stories are insane.

• 28:17Ryan Holiday?

  Yeah, we, like, we think, oh, the Odyssey is cool, like, you, Odysseus, uh, he's a badass, he's like a warrior, he's fighting, he's doing all this stuff. The Bhagavad Gita is basically the same poem.

• 28:29Rich Roll?

  Yeah.

• 28:29Ryan Holiday?

  You know, it's the same, it's teaching the same lessons, but it seems like, uh, this, there's, I, I assume, I would, there's probably a certain amount of racism where we think it's like soft and for pansies and it's like, we think one is like, a poem, but the Odyssey is a cool story. And that's because we've seen like, a bunch of movies and there's other stuff about one and not about the other. So I, yeah, I was trying to make them accessible.

• 28:53Rich Roll?

  Right. Well, in terms of the launching off kind of point for the book, um, you know, contextually, right now, we're in a culture in which, you know, we've never been more, um, starved of our ability to be still, like, we're in this crazy attention deficit era of unprecedented proportions. I mean, you talk about the CNN effect, but, you know, we're in the CNN effect on steroids. Like, it's way crazier than just news being on television 24 hours a day. And it's become increasingly more and more difficult to put the phone down and spend, you know, one minute with ourselves.

• 29:33Ryan Holiday?

  Sure.

• 29:34Rich Roll?

  And we tend to think of this as, you know, a modern epidemic. And I thought it was really cool that you opened the book with this story of Seneca and you realize, like, Oh, this isn't like this has been going on forever. Like this guy had the exact same problem that I had this morning.

• 29:49Ryan Holiday?

  Yes. Yeah, there's and actually I'd written the book without that. I started with so I started with the Lincoln story. That's originally where the book was going to open. There's a story about Lincoln saying there's this city that's a key and that the Civil War can't be won without the key. And so it's like, oh, that's the title of the book. Stillness is the key. That's what's going to be around. And I sent a early draft of it to Robert Greene and he was like, I really like it, but I feel like you have to like root it in where we are right now, which is amazing advice. And he was like, isn't there this letter from Seneca where he's like in Rome? And he's like describing exactly how noisy and loud it is. And it sounds exactly like a modern city. And I was like, yeah, I think there is. Let me go look for that. And I found

• 30:29Ryan Holiday?

  it. And I was like, exactly. I was probably in a hotel room when I found it. It's noisy. I got a bunch of and Seneca just he's writing to his friend and he's basically he's like, it's so loud outside my window that I wish I was deaf, you know, and he's just he's staying above a gym, basically. And he's like, these people are dropping weights and there's people splashing in the pool. There was a guy getting arrested downstairs. Like, you're just like, it, it sounds, it sounded like a summer afternoon in New York City.

• 30:59Rich Roll?

  Right.

• 31:00Ryan Holiday?

  When you just want to blow your brains out because it's so loud.

• 31:03Rich Roll?

  Yeah.

• 31:03Ryan Holiday?

  And, and he's like, but I'm trying to work. And I, and, and he describes that Stoic state, that apathia where like that equanimity where you're you manage to tune it all out and you kind of go into that flow state and you do what you have to do. And that's what stillness is to me. Stillness isn't like the monk who renounces all his possessions. And of course, it's still because he's on a, you know, a 10 year meditation retreat in a beautiful, you know, Buddhist monastery in the mountains. It's like, oh, you can get this.

• 31:38Ryan Holiday?

  Anywhere. And in fact, it's harder to get in real life, but that's where it's most valuable.

• 31:44Rich Roll?

  Yeah, the mastery is in taking it into the world. And when you're somebody like Seneca, or a Fortune 500 executive, or a quarterback, you're shouldering tremendous responsibility and pressure. And there's a lot of external stimuli that's vying for your attention. And the mastery is in trying to figure out what's important and what's not. And, and, and being, you know, able to focus on what is key, actually, in moving you forward on the trajectory that, that, you know, you're here to do.

• 32:16Ryan Holiday?

  Yes. Yeah, that's exactly right. And that's why the people who can do it, either produce this sort of stunning things that take our breath away, or get paid all the money. Because like, no one else can do it. It's really hard.

• 32:29Rich Roll?

  And it was refreshing to hear Seneca, like, you know, sort of struggling with this, grappling with it in real time.

• 32:36Ryan Holiday?

  Yes.

• 32:36Rich Roll?

  Because we think of him as somebody who has mastered these.

• 32:39Ryan Holiday?

  Well, what I liked about Seneca's story is it's not just, hey, this guy has some ability to tune out the noise. Because what if you're sensitive? It's like, also, his personal life is collapsing.

• 32:49Rich Roll?

  Everything's falling apart.

• 32:49Ryan Holiday?

  Everything's, so it, he's also going, like, you're saying, yeah, there are all these outside noises. But oftentimes, the noise is in your head. It's you are the, or, or it's in your, you've got some spiritual malady that's causing. And so, it's that he's able to do it on all the fronts at the same time, and clear, and clear it, and get, and, and I don't think, I don't think stillness is this, I think the other things, people think stillness is maybe that idea of Nirvana, like, you get there, and then you're there. I think it's, it's like, can you get it for 20 minutes? And what can you do in the 20 minutes that you have? You know what I mean? It's like, to talk about football, it's like, the stillness that New England has down,

• 33:34Ryan Holiday?

  being, being down 28 to 3 in the Super Bowl. And just stringing together four or five drives in 12 minutes to pull off this thing, the high, maybe the high watermark of the entire game. And then you go back to regular life and you, you dream about getting back there sometime. Do you know what I mean?

• 33:54Rich Roll?

  Yeah, yeah, yeah.

• 33:55Ryan Holiday?

  You just have these moments where it all comes together. And, and I think the book, and what I've been thinking a lot about is like, how do you build a life? How do you build habits? How do you build systems? How do you build a practice that lets you get there every once in a while? Because when you do, it's just magical. And that's where all the good stuff comes from.

• 34:13Rich Roll?

  Yeah, there's, there's gentle reminders throughout the book that these people weren't born this way. And for most of their lives, they weren't this way. We tend to look at somebody who exudes those qualities and just think like, wow, it'd be cool to be like that person, but I have no idea how to do that. They're just, that's the way they are. But you're saying you're kind of nudging people towards this realization that no, these are, this is very accessible.

• 34:38Ryan Holiday?

  Yeah.

• 34:38Rich Roll?

  That may be fleeting. It's a practice.

• 34:41Ryan Holiday?

  Well, like, so I tell the story in the book of Kennedy and the Cuban Missile Crisis. And there's sort of no one, I think, who embodies what we're talking about more than Kennedy in the sense that he got there. And yet also was the opposite of there all the time. And then also, like, when I think about writing that chapter, like, I, you and I went for a run in Malibu, like, almost exactly a year ago, as I, I just read all the stuff, and I was trying to put it together. And you and I were talking on a run. And I would say, a good chunk of that chapter came together from us doing some sort of physical activity, talking, like, that chapter wasn't, it wasn't like, that just magically came to me, and

• 35:22Ryan Holiday?

  I got it right the first time. It was like, it was just a bunch of different sort of flashes of getting there through different things, like, and, and it came together over time. And I shaped it and, and, but it wasn't.

• 35:38Rich Roll?

  It wasn't, it wasn't a function of willfulness. It was more a function of letting go, which is a big, another big theme in this book, like surrendering and, you know, finding the ability to be present so that these ideas can like congeal in your mind and present themselves more fully formed.

• 35:57Ryan Holiday?

  Yeah, yeah, yeah. It wasn't like some sprint of genius that I pulled out this chapter. It was like a lot of quiet time reading and it was time doing this and time doing that and times just sitting there and, and just putting, putting in the work and eventually you get there and hopefully there's some insight that resonates with someone and helps them do something.

• 36:17Rich Roll?

  A lot of note cards.

• 36:18Ryan Holiday?

  A lot of them.

• 36:20Rich Roll?

  What do you, what do you do with the note cards when you finish a book?

• 36:23Ryan Holiday?

  Um, so they all get scanned in case there's a fire and then I lose them. Uh, and then, uh, I just, they're there. It's like, that book is the raw material or that, that box of cards is the raw material. And I, I mean, they're all just sort of not displayed, but they're sitting there in my office. And it's actually really good because it's like, oh, I remember what I, what I do when I look at those boxes is now I have, you know, for each one of these, there's one, each one of my books is like this box is their own box. It's like, I remember taking that box out of the packaging and there was nothing. And that's what a book is. A book is filling that in.

• 37:06Rich Roll?

  Yeah. So there's a tactile element to it.

• 37:10Ryan Holiday?

  Yeah. Or it's just like, it's a manifestation of the process. It's like, it's like if you run up a mountain, you're like, I remember being at the bottom of that mountain, you know?

• 37:19Rich Roll?

  Right.

• 37:19Ryan Holiday?

  And, and so it's like, I remember when there was zero note cards and now there's 2,000 note cards. And so when I'm starting the next book, it's like, oh, okay. It always starts at zero. Put the stuff together and

• 37:33Rich Roll?

  I've got enough boxes sitting over there to know that I can do this again.

• 37:37Ryan Holiday?

  Yes. And I also, the other thing is the boxes, because I've talked about them, I don't think they make them anymore. The price is like shot way up on Amazon. So I have like 10. So I like, it's almost like in a way like I can flash forward to the end of my career. Like maybe I'll get to these, but it's just like, that's like my whole life right there.

• 37:55Rich Roll?

  Yeah. So they're just sort of gently in the back reminding you that there's more books I need to get written.

• 38:01Ryan Holiday?

  Or just like if you could go, if, if I was like, Rich, you'll have six more cars in your lifetime and they're parked in this parking lot over here. And you'll go through one after another. It's like, it's just a weird manifestation.

• 38:12Rich Roll?

  It's kind of, it's a reminder of your mortality too.

• 38:15Ryan Holiday?

  And, and just the ephemerality of all of it.

• 38:18Rich Roll?

  Right.

• 38:18Ryan Holiday?

  Do you know what I mean? Like, oh, so I'm going to fill these boxes and then, okay.

• 38:23Rich Roll?

  That'll be my life.

• 38:24Ryan Holiday?

  Yeah.

• 38:32Rich Roll?

  Well, back to Kennedy. He's a great, he encapsulates, you know, so much of, of what this book is about in that he demonstrates his ability to, to be still and navigate the Cuban Missile Crisis with, you know, the weight of the, the planet essentially hanging in the balance.

• 38:56Rich Roll?

  And he gets, he gets, you know, everybody through that experience, but he's also a guy who started out as a dilettante. And, you know, has all these family issues.

• 39:07Ryan Holiday?

  His dad bought him a Pulitzer Prize, basically.

• 39:10Rich Roll?

  Yeah, like there's all these, he didn't, he didn't start as this magnificent statesman.

• 39:16Ryan Holiday?

  Yeah.

• 39:16Rich Roll?

  And then later in the book, you kind of revisit him through all his sexcapades.

• 39:20Ryan Holiday?

  Yeah.

• 39:21Rich Roll?

  And you realize like, oh, this guy is, yes, he has this moment where he's able to step up and do this. But he also is very human and flawed in, in many other ways.

• 39:33Ryan Holiday?

  Yeah, it's like during, so during the Cuban Missile Crisis, there's this photo of him and he's leaning over the, like, so you see him from the back. So it's like

• 39:40Rich Roll?

  That famous photo.

• 39:41Ryan Holiday?

  And he's like standing there like this and you can tell he's, I mean, just imagine, think if I was like, Rich, I need you to come up with a solution to this problem. And if you don't, 60 million people die, probably including you and your family, you know, like just the, the weight of that. And, and for him.

• 39:58Rich Roll?

  And everybody's pushing you to make this one decision that you're not sure is right.

• 40:02Ryan Holiday?

  The, and worse, there, it's a very satisfyingly primal and justifiable thing that they're asking you to do. Do you know what I mean? They're like, don't get pushed around. And you're like, I don't want to get pushed around, you know, like they're, they're telling him to do something that would be very seductive. And natural, like they brought Lyndon Johnson into the room and Lyndon Johnson, we gotta bomb the shit out of Cuba, you know, like it's just, that's just weird. And so he resists that and it's so impressive. And yet during one of the 13 days, he asked someone on his staff to drive down this like girl from a liberal arts college and then he has sex with her in a White House or in a, in a DC hotel.

• 40:45Rich Roll?

  Yeah, she was 19.

• 40:46Ryan Holiday?

  Yeah, it's gross. I mean, it's just super gross. And so it, it's, it's, it's not just gross. It's like a man basically preying on a small, you know, the most powerful man in the world, like using his power to, you know, manipulate a young girl, but it's like, for all he knew, this could be like his last night on the planet and he's not at home.

• 41:07Rich Roll?

  Choice that he's making.

• 41:08Ryan Holiday?

  Yeah, he's not with Jacqueline and the kids. You know, it's like, I, I just, when I read that, I was like, what were they doing? Did he tell them? Like, did they know? And he was just pretending he was at work? Did not even care? It just made me feel very sad.

• 41:23Rich Roll?

  So how do you reconcile like this great moment where he's able to, you know, make a decision that changes the trajectory of history? With, you know, the foibles of his personal life.

• 41:36Ryan Holiday?

  So that's like a criticism I've gotten with my books. My answer is like, I don't reconcile them. Like people will go like, oh, you know, Ryan, you know, virtue is the highest aim in Stoicism. And yet in, you know, the obstacle's way, you're telling a story about Erwin Rommel, who was, you know, a Nazi general or Samuel Zemurray, who's like this basically robber baron who, you know, rapes uh, Central and South America as the CEO of United Fruit. I'm not saying you should be like John Kennedy, the person. I'm saying you should be like John Kennedy in the Cuban Missile Crisis, doing this one thing in the same way that we, if you, when you draw an analogy to something, you're not like, or if you say like, oh, this person's fast like a horse,

• 42:20Ryan Holiday?

  you're not saying like, also, you know, they just like shit uncontrollably all over. Like, it's not a, it's not a complete analogy or metaphor. It's, it's the capturing the essence of this one thing in isolation. The idea of the book is like, there's, here's a bunch of people doing the right thing in the right moment. Can you, as a person, put them together? Like, can you put the goodness of Kennedy here? And the goodness of so and so here, and the goodness of so and so here? And avoid the, the, the trap that Tiger Woods fell in or, or, you know? So the idea is like, can you grab a collection of all of the virtues of these people?

• 43:05Ryan Holiday?

  And avoid the vices that either them or other people fell prey to? And come up with like a new combination?

• 43:11Rich Roll?

  Yeah, yeah, yeah. Well, I think it was a, a good and important choice to show that, you know, the rounded humanity of these people, because if you only show the good thing, then you are opening yourself up to that kind of criticism. And we're in a culture right now where, you know, we're judging everybody on their worst actions and deciding that they need to be erased from the record forever.

• 43:33Ryan Holiday?

  Yeah, and, and look, one of the reasons I liked Tiger, I, I like, I learned this from Robert Greene. It's like, you don't just show people observing the laws or like what you're trying to say. Also show the costs or the, the, the, the downsides of violating. Like in the Forty Laws of Power, it's observance of the law, transgression of the law. Like, you're showing both. And so someone like a Tiger Woods was someone who had this intense mental discipline, but had a spiritual bankruptcy. And the idea is that if you don't, if you only have one and not the other. It gets you pretty far, but eventually

• 44:14Rich Roll?

  Yeah.

• 44:14Ryan Holiday?

  it all collapses under the weight of its own hypocrisy or contradictions.

• 44:20Rich Roll?

  The, uh, the Tiger Woods episode in the book, that's, that's probably the example you spend the most time on.

• 44:26Ryan Holiday?

  Yeah.

• 44:27Rich Roll?

  The most number of pages on. And I think it requires that because there's so many chapters to that to really understand it. Um, but you go into it, if I'm not mistaken, it's in the spirit section, right?

• 44:38Ryan Holiday?

  Yes.

• 44:38Rich Roll?

  You divide the book up into basically like mind, body, spirit.

• 44:41Ryan Holiday?

  Right.

• 44:42Rich Roll?

  I think the spirit section could also be entitled daddy issues.

• 44:46Ryan Holiday?

  Yes, of course.

• 44:47Rich Roll?

  Pretty much all these people have like huge issues with their dads.

• 44:51Ryan Holiday?

  Yeah, sometimes it's a mommy issue, but it's mostly dads.

• 44:54Rich Roll?

  Yeah, with these guys.

• 44:55Ryan Holiday?

  Kurt Vonnegut is like, our parent, our mom and dad, they screw us up or something like, you know, it's like, they try, but it's all their fault.

• 45:02Rich Roll?

  Right. Um, and there were certain aspects of, of Tiger's story that I, I didn't know how like, how intense that was with his dad.

• 45:10Ryan Holiday?

  Oh yeah. I think, I think, and this was a different media environment than we live in now, but I think we all sort of bought into this myth that like, oh, Tiger Woods just had like, one of those hard driving like show parents. And it's like Tiger Woods' dad may have been a psychopath. Like, like it's mu- like Tiger Woods' father was deeply abusive, was like, uh, Michael Jackson's father level bad. You know, even that we go like, oh, you know, he was, Michael Jackson's dad was bad. It's like, no, Michael Jackson was like a horribly abused victim of a monster, essentially.

• 45:47Rich Roll?

  Yeah. And it produced this great champion, but then we all saw, you know, the wreckage ultimately that was manifested by that.

• 45:55Ryan Holiday?

  Creating a very fragile champion.

• 45:57Rich Roll?

  Right. And then we have the great comeback also.

• 46:02Ryan Holiday?

  Which is not in the galley. It's fixed in the.

• 46:04Rich Roll?

  Right. Yeah. I noticed that because I have the galley and I'm reading it. And I was like, oh, I wonder if he's going to get to 2009. And you kind of mentioned 2009, but you don't go, go into detail on it. So in the final book, there's more.

• 46:15Ryan Holiday?

  Well, I just, I like, so I captured the downfall and then it was nice to see him winning that major and to like, he, the first thing he does is hug his son at the end of it.

• 46:24Rich Roll?

  Yeah.

• 46:24Ryan Holiday?

  So, you know, it actually in the galley, it's a little bit more depressing because it's like a story with no redemption. And I do like that he redeemed himself. Um, so I, I like, I, I, I, I think it was, it was missing a 5% change that, that it was able to dial. I mean, it's, it's great that he won. I think, I think people are now willing to gloss over just how dark and bad it was, which is, you know? We do the same thing with Steve Jobs. We go, he came back from getting fired from Apple. It's like, yeah, he was horrible. He should have been fired from Apple. And probably it was, probably on paper, it was crazy to bring him back. You know? The Tiger Woods story is very dark and yes, very driven by daddy issues.

• 47:09Rich Roll?

  Yeah. Well, from a very top level, the book really, you know, when you are trying to drive the reader towards this understanding of what it means to be still and the importance of stillness, it's, it strikes me as, as really this journey to, um, learn to turn inward and, and really crowd out the externalities. It's the externalities that create the confusion and the stress and the anxiety and, you know, the competitive nature and the measuring and all of those things that prevent us from being clear on, you know, what it is, you know, that is ultimately driving us.

• 47:48Ryan Holiday?

  I think that's true, but I think maybe that's something that Eastern philosophy people misread in it. They go like, oh, okay, like I gotta eliminate noises. I gotta eliminate distraction. I gotta live a quieter life, blah, blah, blah. It's like Tiger Woods had like a monk-like obsession with golf, but was so broken spiritually that it, it wasn't like noise in Tiger Woods' ear that was making him unhappy. It was the voice inside of his head. You know what I mean? And, and so I think you can fix, it's, I think, I'm trying to say you gotta attack it from all angles. Like if you have mental discipline, but then, you know, you have this.

• 48:28Ryan Holiday?

  Deep insecurity inside you that's, you know, gonna never, never feel like you're enough. In a way, almost your mental discipline is your worst enemy because it's just gonna be, you think like, oh, I, if I win a Super Bowl, I will be happy, you know? Or dad will love me if I become a billionaire. And actually-

• 48:46Rich Roll?

  You have the Michael Jordan example of that famous speech that he gave.

• 48:50Ryan Holiday?

  Yeah, yeah. And then also, it's like, you have those things, but you eat terribly and you don't take care of yourself physically and you have bad habits. It all feeds, it, there's, there's no like, one magical thing you do and you have stillness. It's this like, process of, of getting there.

• 49:09Rich Roll?

  Right. So if you're very mentally, uh, sound and disciplined, but you don't take care of yourself physically, or you have like, a pa- you have all kinds of crazy emotional problems, synergistically, this is not gonna work. It might work-

• 49:27Ryan Holiday?

  Yeah.

• 49:28Rich Roll?

  Towards a, a, a short-term goal-

• 49:30Ryan Holiday?

  Yes.

• 49:30Rich Roll?

  As a life.

• 49:31Ryan Holiday?

  Yes, yes, exactly.

• 49:33Rich Roll?

  At all of these things.

• 49:34Ryan Holiday?

  Yeah. So it's like, yeah, your concentration helps you become a great artist. But what's motivating you to become a great artist? It's the sense that, you know, if you're famous, now you matter. Or that if you, uh, get accepted by this cool crowd, now you'll feel good about yourself, you know, or-

• 49:57Rich Roll?

  But then it begs the question of, you know, who are, who are you without those things, right? Like, you talk about Kenzo the archer, and, you know, this idea of like, letting go of, of hitting the bullseye, being detached, like, holding on to things loosely, and then trying to figure out how you square that with, well, if I wanna be a champion, like, I've gotta be, you know, my, my eyes have to have to be on the prize. Like, I've gotta be driven in some respect, and it's this balance of those two things.

• 50:26Ryan Holiday?

  Yeah, Billie Jean King, the tennis coach who was saying, it's like, so what makes you a great- Athlete is your relentless desire for improvement and never being satisfied with the current state of your performance. The irony is that that is obviously the attitude you need to become the best. But it is also antithetical to enjoying. Your life, right? Not only enjoying being the best, but to even acknowledge that you got to the top and you are the best. You know what I mean? Right. Because you're like, you're focusing on how, how much left you have to do or how bad you feel after that.

• 51:07Ryan Holiday?

  Like you're, you're just never, you're never gonna feel good because you have this quirk in your brain that makes you always focus on what's wrong. And, you know, like, it's, when I wanted to be a writer, I like, it would have been like, oh, I could have a book that's making it. And then quickly your mind's like, oh, well, actually, like, what if it was a bestseller? What if it sold a million copies? Or what if you had a whole bunch of books? Or, you know, what if you've won this award? Or what if, you know, like, the idea that even one, like, if you told me at the opposite, or the, sorry, the outset of say obstacle, that one person in professional sports would have read the book, I would have been like, done, that's success. I'll settle for the, like, I accept your offer, that's it.

• 51:51Ryan Holiday?

  But then you're like, well, why hasn't so and so read it? Or, you know, like, you know? And there's that other guy over there that sold more books. Totally. And on the one hand, that's good, that can one, keep you humble. Like, I once asked Steven Pressfield, I was like, wow, what's it like to sell like a million books? And he was like, he's like, I mean, he's like, Unbroken has sold like 10 million copies. And, and, and I was like, that is like a good attitude because like, it doesn't, you're not like sitting, look how awesome I am. I know some of those people are like, they're very quick to tell you how many copies they sold, as if it says something. And, and so it keeps you humble, it keeps you hungry, but at the same time.

• 52:29Ryan Holiday?

  How grateful, it also deprives you of being grateful for what you've done.

• 52:33Rich Roll?

  Yeah.

• 52:34Ryan Holiday?

  And that gratitude and appreciation you've earned. So you're, but you're depriving yourself of it.

• 52:40Rich Roll?

  Yeah. So the solution lies in falling in love with process, really.

• 52:45Ryan Holiday?

  I think so, yes.

• 52:46Rich Roll?

  I mean, you talk about, the word is enough. It comes up in the book a lot.

• 52:50Ryan Holiday?

  Tiger was his dad called it the E word.

• 52:52Rich Roll?

  The E word that like Tiger and his dad could never utter out loud. That, that, you know, leaves him, you know, incredibly unhappy as a human being. But then you bring up the example of Heller, who, you know, writes this amazing book and then goes on to continue to write books and kind of lets it go. And is, is, is happy with his circumstances and yet still very productive.

• 53:18Ryan Holiday?

  Yeah. Yeah. So Joseph Heller is at a party with Kurt Vonnegut at the house of this billionaire. And Vonnegut's like sort of needling him and he's like, hey, you know, you wrote Catch 22, but you know, this guy made more money than you, than you will ever make in your life, like at work this week, you know? And, and Heller goes, but I have something he'll never have. And he says, what's that? And he says, the, the notion that I have enough. And I think we are all deep down, very scared that if we ever say that word, that's the moment we become complacent and the guy behind us passes us. And in a way it is like, if you're running a race and you're like, oh, this is fast enough.

• 54:02Ryan Holiday?

  Like that's when you get passed. So there is that element of it. But at the same time, like, so you're not allowed to be happy with the fact that you wrote one generational defining, like, you know, classic novel that helped millions of people and defined, you know, what that experience was for, for a whole, you know, again, a whole generation. And, and like, my favorite thing from Heller is this reporter goes like, you know, you've never written anything as good as, as Catch 22 again. And he says, who has, right? So like, he is sad. He, they're like, I like that. That's just great. Like, um, maybe I won't ever write a book as good as Ego or, or obstacle.

• 54:45Ryan Holiday?

  Maybe they won't sell as many copies like, but that's not going to prevent me from continuing to write. I don't think, you know, I don't want it to, and I don't want, I, I, what I want to do is love the process. Like, I want to love sitting down, starting the next one.

• 55:04Rich Roll?

  Right. And part of what drives the process is understanding that there's a destination. Like, it's, it's, it's this tension between these two that I think, look, these are the questions that go back, you know, eons that we struggled with, like competitiveness versus letting go. And you talk about like, you know, the no mind and being totally present and in the moment. And how do you reconcile that with deep thinking? And how do you, how do you square being a very competitive person with these ideas about letting go and surrender? And like, you know, I have my own personal stories with this with, you know, I've introduced to these ideas in, in, in sobriety. I'm like, surrender, like, give up, like, like, no,

• 55:44Rich Roll?

  I, that's not who I am at all. And yet, when you really can grok what that means and implement those truths into your life, you realize that your life becomes much larger and it flourishes. And, and, and you don't have to, that fear of like, well, this is who I am, this story that I tell myself about who I am, I'm driven by these, what you learn later are really character flaws, character defects that flame out quickly and, you know, end up, you know, causing more damage than good.

• 56:13Ryan Holiday?

  Yeah. And I think the East and West sort of align on this. I, I think it's Confucius, but so he, you know, he tells one student to do, you know, he's like, you gotta, like, you know, avoid your parents. And then he tells this other student, like, you gotta go figure out how to love your parents or something like, I forget what it is. And this other student's like, but you just told them to do opposite things. And he was like, one student needs X and the other needs Y. And I think what I like about Eastern philosophy that I think Western philosophy is less explicit about is just this sort of like embracing or tolerance for paradox and

• 56:54Ryan Holiday?

  Contradiction and absurdity. Do you know what I mean? Like, it's just like, like,

• 56:58Rich Roll?

  Like the Zen Koans.

• 57:00Ryan Holiday?

  Yeah, like, they're supposed to be confusing. I think that's what they really, I think enlightenment is like, oh, this, maybe it doesn't really mean anything. You know, like, that I, it's the, it's the idea that there is what one hand clapping is. Maybe it's just like, maybe what enlightenment is, is sitting with that a long time and going like, maybe this is a trick question.

• 57:20Rich Roll?

  Right.

• 57:20Ryan Holiday?

  You know, or something.

• 57:21Rich Roll?

  Well, with Stoicism, there's an inherent practicality and applicability. Like, you can read that and you can immediately implement these things into your life and improve your quality of life. But the eastern traditions are much more ephemeral.

• 57:34Ryan Holiday?

  Yeah.

• 57:34Rich Roll?

  Right? And, and perhaps that's, you know, where it gets frustrating and that's why it's not as cool as Stoicism, because I think it's demanding more of people.

• 57:44Ryan Holiday?

  Yes.

• 57:44Rich Roll?

  Because you, you really have to, you know, reckon with these things in a deeper way to really get to, to the point where you can even understand what they're trying to communicate to you.

• 57:54Ryan Holiday?

  Yeah. And, and Kenzo, who's the archery instructor in the Zen and the Art of Archery, I think he would have these Western students and they were like, show me how to do this. Like, I want to get better at this. And I think part of the reason his, his instructions were so vague and contradictory and weird was it was a overreaction to that idea that like, this is the five step process for becoming a master of archery. You know what I mean? Like,

• 58:25Rich Roll?

  And becoming a master at anything, really. Like, basically saying, master yourself before you even think about like, what the arrow, you know, where the arrow is going to go. Like, you have to become

• 58:36Rich Roll?

  somebody who knows how to be present, who knows how to, you know, remove distractions from their lives, who knows how to focus deeply. Like, all of these things are Things that you have to devote your entire, you know, years and years and years to get good at.

• 58:50Ryan Holiday?

  And that's that, I think, you know, a big part of it is just like surrendering to whatever the master is telling you. And that's the hardest thing. Like, we, it's like, the student, it's almost like Eric, like when the student's like, "Teacher, teach me this", you know? And I think with the, that sort of Zen Buddhist sort of archetype is, is like, "You don't tell me what to do. I tell you what to do." You know what I mean? Like, like, it's, I think, and, and that's where that higher power idea comes in too. It's like, "Oh, wait, like, you're not in charge." Like fundamentally accepting that you're not driving the process. The process is driving the process. And you have to submit to that. And I think it's not, I don't sit down and go like, "I'm gonna grab a book here out

• 59:33Ryan Holiday?

  of, from brute strength." It's like, "No, I'm gonna open myself up and I'm gonna follow the steps and it's going to ensue if I'm patient enough and accepting enough and vulnerable enough."

• 59:46Rich Roll?

  Yeah, to have an open mind, to be teachable, to, to be able to get into that, you know, Fred Rogers childlike state where you're able to hear something that might be at odds with the way that you see the world.

• 59:59Ryan Holiday?

  Yeah, yeah.

• 1:00:08Rich Roll?

  It was interesting that you brought 12-step into it.

• 1:00:12Ryan Holiday?

  Did I get that right, by the way?

• 1:00:14Rich Roll?

  You did, yeah. I mean, it's, it's tricky to, to communicate what that's all about. And it took me a really long time to really understand what that was about. But I think you're very accurate in the sense that a lot of people are reticent to go into that community because of their hangups around, you know, the word "God" and what it means to, you know, accept that there's a higher power. And, and truthfully, there is no religious strain in it whatsoever. It's just asking you to believe that something is greater than yourself. And addicts by their nature are control freaks and they, you know, have strong opinions about how they see the world and a lot of them are emotionally damaged

• 1:00:54Rich Roll?

  and have hangups around the church, et cetera. But all, all it's saying, like, you could be the most... Anti-religious person of all time, but what I always say to people who are struggling with that is like, listen, you're you for the life of you, you can't stop drinking, dude. So clearly you can't control that. And you go into this group and there's all these people here who figured out how to do it. And they've been doing it for a little while. Like, maybe they know something you don't like they're they're your higher power.

• 1:01:25Ryan Holiday?

  Yeah.

• 1:01:25Rich Roll?

  They can be. You could just look at them and say, this group consciousness

• 1:01:31Rich Roll?

  has more strength than I do.

• 1:01:33Ryan Holiday?

  Yeah. And I think I just think it's so, it's such an epitome of the attic mind and of of our mind as a it's like, it's like, okay, so you enroll in the you enlist in the army and the drill sergeant's like, you know, shave your head and make your bed and blah, blah, blah. And you're like, well, none of these things, Matt, you're like, giving them your opinion. Like, this is a like, a 300 year old institution that's created the greatest fighting force in the history of mankind that's done all these things. And you, this person who's thought about it for like, eight seconds, who's never done anything in their life, is convinced that you know better.

• 1:02:08Rich Roll?

  Right.

• 1:02:08Ryan Holiday?

  And and I think it's it's like, it's I think a huge part of it is just like, it's almost the fact that it's a hard thing to do is what makes it so powerful. And it's like, it's like, that's the initiation into the fraternity. Like, are you willing to do what we say? Do you I think there's a part of I think that works just.

• 1:02:28Rich Roll?

  Yeah, it requires humility. I mean, the analogy in 12 step would be you walk in and they're like, go make coffee, sweep the floor, like, you know, here, you have a commitment, you have to say hi to every person that walks in the room. And you're like, what does this have to do with not drinking anymore?

• 1:02:40Ryan Holiday?

  Yeah. It's like, don't ask questions, just do it.

• 1:02:43Rich Roll?

  And and I struggled with that for a long time. And when I finally I was so broken that I just let go of all of that. And I just said, just tell me what to do and I'll do it.

• 1:02:50Ryan Holiday?

  Yeah.

• 1:02:51Rich Roll?

  My life changed.

• 1:02:52Ryan Holiday?

  Yes.

• 1:02:53Rich Roll?

  And I think a big part of that is just being malleable and teachable.

• 1:02:57Ryan Holiday?

  Yes. No, I think that's true. And I think.

• 1:02:59Rich Roll?

  And it's it's the willingness to ask for help and also, perhaps even more powerfully, the willingness to accept help.

• 1:03:07Ryan Holiday?

  And look, I'm still an atheist. I don't I can't get my I did my head around the idea that there is a God, particularly like a Christian God, like I just have trouble with it. But at the same time, what I struggle with would at least keeps my mind open. And then what sort of inspired this chapter is it's like, but. Basically, every person that I admire that's ever lived for almost all of human history, they were able to wrap their head around this. Like, why am I better than them? Why am I smarter than them? I don't, I can't, that can't be right. Do you know what I mean?

• 1:03:41Rich Roll?

  So where does that leave you?

• 1:03:42Ryan Holiday?

  It leaves me with at least, at least the, like, it definitely makes me go from atheist to agnostic, right? Which I think is a big step, right? Because atheist says, like, I know there's not a God. Agnostic says, I don't fucking know. You know what I mean? So I think it at least gets me there. And then there are moments where I can go like, this is just all incomprehensible. There must be something. Do you know what I mean? And so it's gotten me closer to the idea of there being a higher power, or at least the idea that like, I'm very comfortable going like, I'm not in charge and I'm not choosing really any of this.

• 1:04:22Rich Roll?

  Yeah. And so how do you think about that with respect to stillness? Like, somebody's connection to their form of faith and?

• 1:04:32Ryan Holiday?

  I mean, I don't, I just, I find it doesn't strike me as a coincidence that the stillest people are all the ones, and not religious in the fundamentalist sense. Those are probably the most miserable people, and they're probably compensating for the intense doubt and self-loathing that they actually feel. But, you know, the people who undergo the, you know, the Jesus on the cross in this horrible pain, asking for forgiveness for the people who inflicted it on them. I mean, that's just like incredible to wrap your head around, you know? Or just, just the, you know, the, the sort of the prayer, the person falling to their knees and praying when the world is, you know, the weight of the world is on their shoulder.

• 1:05:17Ryan Holiday?

  I just find that to be so beautiful and inspiring. And it's like, how do I, how do I get there? And then going, you know, even back. Back to the idea of the gods, just this idea that like, oh, man, there are these things happening that that are beyond us and that that you're, we are not the central driving forces of our lives through the universe. I can get there pretty easily. The Stoics had this idea that that so the logos, which is actually means the way in the Bible, but it predates Christianity. You know, Marcus really is is ideas that we're like a dog tied to a cart. And so like, the dog can fight against the cart, dog can lay down

• 1:05:59Ryan Holiday?

  and be dragged by the cart, or the dog can run alongside the cart cheerfully. I can get there.

• 1:06:04Rich Roll?

  Yeah. Well, the example from the book that springs to mind is the astronaut who looks at Earth.

• 1:06:10Ryan Holiday?

  Yes.

• 1:06:10Rich Roll?

  When they're when he's orbiting and and extrapolating on that idea, the more you kind of look at, you know, the the magnitude of the universe, or the, you know, when you drill down to the tiniest subatomic particles, like, stuff gets crazy, like, our brains can't even.

• 1:06:29Ryan Holiday?

  Yeah.

• 1:06:30Rich Roll?

  Begin to understand what's happening. And for me, like, that's where I can find a healthy place of awe and wonder.

• 1:06:37Ryan Holiday?

  Yes.

• 1:06:38Rich Roll?

  And that and that place of humility also, like, we don't, we don't, maybe someday we'll understand this, but maybe not. Maybe it's beyond our mental capacity to fully grasp. And rather than that, making me uncomfortable, I actually find I find comfort in that.

• 1:06:55Ryan Holiday?

  Mm hmm. Yeah, I mean, I was I read this book a couple of years ago, and it was talking about like, basically, like, the history of like, extreme weather. And it was saying that, like, we basically didn't know what a tornado was until, like, right around the time of the founding of America. Because they don't really have tornadoes that much in Europe. And it's like, sort of an American thing. It's like a Midwest thing, basically. But like, so, so there would be these reports where it's like, all of a sudden, like, One side of a street was destroyed and not the other side of the street, you know? And you're just like, what? And so when the world was so inexplicable and we had so little science, it was much easier to go like, oh yeah, God did this, right?

• 1:07:36Ryan Holiday?

  Like, I could imagine that you hear this terrible sound and you you run and you hide and then you come back and it looks like God just destroyed, smited down the sinners or whatever. It was like, so, and this, you know, you go back further to the the the Greek or ancient idea of the gods. Like, when the universe was much harder to explain, it was easier to get there. And so in a way, it almost, it's almost a greater challenge, but a more meaningful challenge to seek out that awe and to look at it. And so, I mean, talking about going to space, have you seen like the blue marble photo? Like, it's that famous iconic photo of Earth from space. It's like that photo was taken in like 1971.

• 1:08:19Ryan Holiday?

  Like, we, that's, that's like 50 years ago. For the first time, we saw Earth from not Earth. And so when I think about that, I go like, wow, that's like, that gives me a little bit of that humility and awe, you know, to look at that photo.

• 1:08:35Rich Roll?

  But it's so fleeting. You know, you think like, that is such a magnificent thing that should just permanently alter our perception, you know, of who we are and our importance and all of that. But it evaporates almost immediately and we're back to our phones and our daily lives. And, you know, the, the, the example that beautifully illustrated that in the book is, is Abramovich's art installation at MoMA where for like 79 days straight, she stares at people all day long. Like, walk us through that.

• 1:09:06Ryan Holiday?

  So, uh, everyone should watch the documentary, The Artist is Present. It's incredible. I think it's on Netflix. But basically, so she's doing this retrospective at MoMA of her entire career. And, uh, she's a famous, you know, creative but provocative performance artist. And that the exhibit is called The Artist is Present. And because that's what she is, she's present in her work. So she comes up with the idea of like, I'm going to be present for every day of the exhibition. And she gets a table not like this and they sit there and a line of people, one after another gets like five minutes to just sit across from her and she just sits there and stares at them in the face. She doesn't go to the bathroom.

• 1:09:46Ryan Holiday?

  She doesn't get up. She takes, she goes to, she goes home every night, but like.

• 1:09:52Rich Roll?

  Like an eight hour shift?

• 1:09:53Ryan Holiday?

  Basically an eight hour shift, immobile in a chair. And the only thing she gets is between people, she looks down, gathers herself and then looks up.

• 1:10:02Rich Roll?

  She gets to go to the bathroom?

• 1:10:04Ryan Holiday?

  No.

• 1:10:05Rich Roll?

  For eight hours?

• 1:10:05Ryan Holiday?

  For eight hours.

• 1:10:06Rich Roll?

  And she doesn't eat or anything?

• 1:10:07Ryan Holiday?

  She doesn't eat, she doesn't do anything. It's like inhuman. But it like, so they ask her collaborator, it's like her ex-husband, but her former artistic partner and they like described to him what she's going to do. And they go, what do you think? And he goes, I have no thoughts, only respect. Which is like, kind of like what I think of your, your, your Iron Man of Iron Mans. Do you know what I mean? Like, I don't, it's like so incomprehensibly

• 1:10:34Ryan Holiday?

  impressive that it's, you're just like, wow, okay. You know what I mean? Like, you're just like, wow. It, it just, you're like, a human did that.

• 1:10:42Rich Roll?

  Well, I think with her, like when I read that in the book, like no, I have no thoughts, just respect. I was also thinking like, she has no thoughts either.

• 1:10:54Ryan Holiday?

  Right.

• 1:10:54Rich Roll?

  Only respect, like she.

• 1:10:55Ryan Holiday?

  For that, for that.

• 1:10:56Rich Roll?

  She shows up and sits across from another human being and is fully 100% present for that experience. And, and, and, and there's nothing more respectful that you can do for another human being than to give them your undivided attention.

• 1:11:15Ryan Holiday?

  And the crazy thing is that like, even though she's not saying anything, even though none of that is like in the description, like everyone immediately feels like in the documentary, you can watch people, dude, sit down and they would just start weeping. Because they'd never. I mean, I've never experienced that. I mean, maybe I have, but you know what I mean? Like, I've never just, it's probably what people, and I'm not comparing her, but that's probably what people felt being near Jesus. Or it's one of the, like, when you, when one of these prophets, and look, sometimes they're mentally ill, that's where they're getting it.

• 1:11:48Rich Roll?

  Hugging Alma, do you know about Alma, the Hugging Saints?

• 1:11:51Ryan Holiday?

  No.

• 1:11:51Rich Roll?

  Um, she's this woman, like, this, you know, enlightened, you know, higher consciousness, and she travels the world, and wherever she goes, thousands of people show up and wait in line just to, you know.

• 1:12:04Ryan Holiday?

  Sure.

• 1:12:05Rich Roll?

  And she gives everybody a hug. I've had that experience, too, and it's like, whether she's enlightened or not is neither here nor there. It's just, somebody who is so present for that kind of experience is a rare

• 1:12:15Ryan Holiday?

  Yes.

• 1:12:16Rich Roll?

  thing.

• 1:12:17Ryan Holiday?

  Yeah, and then, we know that, and yet, we live our lives the exact opposite of that.

• 1:12:23Rich Roll?

  Right. And so I feel like her, the artistic, the installation is this twofold thing. Like, one, to provide people with that, a glimpse of what that can be like, that experience, but also to underscore and illustrate the ephemerality of the whole thing.

• 1:12:39Ryan Holiday?

  Yes.

• 1:12:40Rich Roll?

  Because everyone just immediately goes back to, you know, they just, it lapses immediately, or all the bad behavior that gets manifested in people jockeying for position in line, and...

• 1:12:50Ryan Holiday?

  Well, this one woman, she, you, she gets up there and she takes her dress off, and it was clearly she'd, she'd decided not to wear underwear. So, like, she'd planned out, like, so, you can track, Marina is completely present, and meanwhile, this woman spent weeks planning and executing a stunt, and who knows what her intention was. I don't think she was like, "I just want attention," but it was like, she was the opposite of Marina.

• 1:13:18Rich Roll?

  Uh huh.

• 1:13:18Ryan Holiday?

  You know what I mean? And that she was calculating and thinking about the rea, like, and that's, to me, who we, what we are, most of the time.

• 1:13:25Rich Roll?

  Right, and, and so, that's, but I think that's the real statement.

• 1:13:29Ryan Holiday?

  Yes.

• 1:13:30Rich Roll?

  In the art install, in, in her performance, right, is to, is to demonstrate that this is, this is what we do as human beings.

• 1:13:37Ryan Holiday?

  Yes, and that, that even, what does it say, that presence for five minutes is a life-changing...

• 1:13:46Ryan Holiday?

  It's like a ride at Disneyland. Do you know what I mean? It's like, everyone's got to go on Splash Mountain one time. Everyone's got to go see Mount Rushmore. Everyone's got to see the Mona Lisa. It's not, even though any of us could get it ourselves at any moment.

• 1:13:59Rich Roll?

  Right.

• 1:13:59Ryan Holiday?

  We want to pay to see it at a museum and then wait in line and then.

• 1:14:05Rich Roll?

  And try to distract the person and throw them off. Like, our goal is to like, you know, just ruin it and destroy it.

• 1:14:11Ryan Holiday?

  Yeah, yeah. It's like, I wanted to, you know, scribble on the Mona Lisa instead of just take it in.

• 1:14:16Rich Roll?

  Right.

• 1:14:17Ryan Holiday?

  Or I gotta take it, like, this is a little, like, smart, I think this is 2010, so it's not, you see people in the audience using flip phones, you know, uh, which I know, the smartphone's definitely invented, but they had not consumed, uh, the world.

• 1:14:32Rich Roll?

  Selfie culture hadn't completely.

• 1:14:34Ryan Holiday?

  Yeah, I don't know, Instagram might not have existed yet. But the, the point is like, it wasn't quite like, hey, let me show you that I did this. But a lot of people were there clearly to just get it off their bucket list.

• 1:14:48Rich Roll?

  Wild.

• 1:14:48Ryan Holiday?

  Yeah.

• 1:14:49Rich Roll?

  So her being this, you know, pillar of presence, somebody who's able to root themselves in the now and this experience of, of no mind, um, let's, let's, you know, butt that up against the importance or value of deep thinking. And how those two things kind of, um, contradict, but also can live complementarily.

• 1:15:17Ryan Holiday?

  Well, so I was talking, I was actually talking to, I don't, I don't think it's a problem to say that. So I was talking to Sean McVay this morning, who's the coach of the Rams. And it was, so on the one hand, you want to be present, you want to go with the flow, you want to do, you want to do all that stuff. And then he was upset about something that he'd seen at practice, right? And I watched him sit there in his office. Work himself out of acting on that anger. Do you know what I mean? Like, he was like, I didn't like how we practiced today. I'm gonna, like, I'm disappointed in the team. We're better than this. I'm, uh, but instead of, he actually, he canceled. Yeah, I think I can say this.

• 1:16:00Ryan Holiday?

  He canceled the team meeting that they were about to have because he didn't want to go in there and unload on everyone.

• 1:16:07Rich Roll?

  Uh huh.

• 1:16:07Ryan Holiday?

  Because it would have made him feel better, but it wouldn't have solved the problem. Right? And he didn't, he couldn't yet, he didn't have a handle on what had caused the problem and what the solution was yet. And so it's this balance of like, yeah, let's be where your feet are. Go with the flow. Let go, you know? Don't suppress your emotions. And yet also objectively, we know a large portion of our emotions are harmful and destructive and, you know, short term. And, and what you need is the ability to like zoom out, see yourself from a distance, extrapolate out into the future and go, what will happen if I do X? Like Kennedy and the Cuban Missile Crisis is totally present and yet at the same time,

• 1:16:52Ryan Holiday?

  working out the decision tree of if I do X, they will do Y and then I will be, do this and where will that lead us?

• 1:16:59Rich Roll?

  Yeah.

• 1:16:59Ryan Holiday?

  So it, that's what I mean where it's like, that's not a contradiction. That's just fucking life, you know? Life is complicated and sometimes the situation calls for A and sometimes it calls for the opposite of A.

• 1:17:10Rich Roll?

  Yeah. I mean, the master in that situation would be detached emotionally from what was transpiring in front of him and would be present enough to have clarity on what the next best decision or action would be to take and would be able to fluidly implement that in the moment and would not have canceled the meeting because that person would have been able to comport themselves and communicate in a way where it could, you know, culminate in a productive result.

• 1:17:40Ryan Holiday?

  Yeah, although I wouldn't, I, I don't know if I'd say like that he's somehow short of mastery. I think it's more, he's like, um, I know where I am right now and I know where I'm going to end up. After I work through this, so I'm gonna give like, so Kennedy in the Cuban Missile Crisis, he has this expression, he says, I want to use time as a tool, not as a couch. And what he means by that is like, I'm not gonna sit back and just do nothing. I'm gonna, I'm gonna give myself time and space so I can use it. And I, what, what Sean was doing is going, if I react now, it will be out of anger or frustration. But if I can think through this and come to a solution, I can not only solve this problem,

• 1:18:23Ryan Holiday?

  but I can also model to my players, like, the importance of not being ripped around by your passion. He's like, how can I, how can I get mad at a player who, objecting to a bad call from a ref, gets a flag and sends us back 10 yards? And then turn around and do that in practice?

• 1:18:43Rich Roll?

  The distinction that I see in that is, he had the self-awareness to realize that he was not gonna be responding productively, but that he was gonna be reacting emotionally.

• 1:18:51Ryan Holiday?

  Yes.

• 1:18:52Rich Roll?

  And that self-awareness was such that he was able to put the brakes on his original plan and not make that mistake.

• 1:18:58Ryan Holiday?

  Yes.

• 1:18:59Rich Roll?

  I guess what I'm saying is, the master wouldn't have even had to go through that calculus, because they would be in a place of...

• 1:19:05Ryan Holiday?

  Yes.

• 1:19:06Rich Roll?

  They would have the capacity to respond. And I think the distinction with JFK is, he needed to buy that time for himself, but he also realized it would be productive for Khrushchev, because he knew that Khrushchev, over to overtime, would come to a healthier realization about what the next best thing would be.

• 1:19:27Ryan Holiday?

  Well, and so two things, actually, that was something I talked to Sean about, and it was like, you're, one of the things he was frustrated with was how the players had stepped, that, that none of the players had stepped up in practice and solved the situation, and that he didn't feel like it was, he didn't want to be the coach that fixes everything. This is what you want a great leader on the field to do. And so the idea that he would jump all over them and tell them exactly what the problem was, and not give them time to fix it themselves, themselves, was actually only compounding the exact problem he was hoping.

• 1:20:01Rich Roll?

  Yeah, I get it.

• 1:20:01Ryan Holiday?

  You know what I mean? So it's like, it's like, my problem is nobody stepped up on the field in the moment and was like the leader and said, come on, guys, let's do this. Right? And he's like, but what if, what if they do it in the hall? On the way to breakfast this morning? It's not as fast as I want, but it's, you know what I mean?

• 1:20:19Rich Roll?

  Yeah, I get it.

• 1:20:19Ryan Holiday?

  And so I, I think that's really important. And yeah, that is what Kennedy was doing in the missile crisis. He's like, I don't think Khrushchev thought this all the way through. If I give him some space, he'll come to his senses. I'm not going to let him walk all over me, but I'll let him figure this out. And I'm not going to make it worse. I'm not going to back him, not going to put him in a position where he can't do that.

• 1:20:38Rich Roll?

  Mm hmm.

• 1:20:39Ryan Holiday?

  And, and I would guess someone like, I mean, Sean has only been a head coach for a few years. He's already one of the most sort of ascendant, promising coaches of an entire generation. I mean, he's my age and he coached a team in the Super Bowl. It's incredible.

• 1:20:50Rich Roll?

  Yeah.

• 1:20:51Ryan Holiday?

  But I would, yeah, I would imagine him in 15 or 20 years, when he's been, when he's seen this 15 times, that's when you become the master and you go exactly what you said. You, you're just like so intuitive, you can't even explain how you knew exactly what to do in that moment. And, and yeah, it's probably a, a thing you get.

• 1:21:12Rich Roll?

  So when you're, you're there and you're observing this, do you say something? Like, are you just watching?

• 1:21:17Ryan Holiday?

  It's both. I mean, on the one hand, like, I'm just a student of all these things. So I love just being a fly on the wall and I'm learning and I love seeing, it's easy for me to talk about these things, philosophy. It's even easy for me to read a bunch of books on the Cuban Missile Crisis. But I'm never going to be in the Situation Room when that's happening.

• 1:21:35Rich Roll?

  Yeah.

• 1:21:35Ryan Holiday?

  So I'm always, one of the reasons I say yes to speaking things, or I even, you know, I have my company that works with authors and brands is that like, it's putting me in a position to just see stuff that I can then translate into my writing. And then, yeah, people ask for my advice and, and I, I, I offer it. I don't know how helpful it is, but you know, I, I, I just love, to me, like, I learn a lot when I go, like, I'm talking to them about stuff, which is stuff I know about, but I really am there to see stuff I don't know about.

• 1:22:04Rich Roll?

  Yeah. I'm still trying to wrap my head around. This distinction between presence and thought in the sense that we have Eastern traditions that talk about, you know, this idea of no mind, like focus on the breath, like the idea is to, you know, really try to broaden those moments where your consciousness is not invaded by narrative.

• 1:22:33Ryan Holiday?

  Yeah.

• 1:22:34Rich Roll?

  Right? And that provides the space and the calmness and the stillness for inspiration, for correct action, for all of these things versus what would be more of a, in the, in the tradition of the Coens, like,

• 1:22:51Ryan Holiday?

  Yeah.

• 1:22:51Rich Roll?

  let's grapple with these, you know, the, the mental gymnastics of a very difficult problem to train our brains to learn how to take these right actions.

• 1:23:03Ryan Holiday?

  Yeah, I don't know. I mean, there's this one sort of Stoic, he's, he's almost more of a cynic, but he's just sort of Stoic. His name's Aristo and he's this early Stoic, he's sort of a contrarian. And he was like, the wise man doesn't think, simply pops into his head what the right thing to do is. And that sounds like a very Eastern thing. I just, I just don't know if that's true. And, and, and I know from my experience that maybe it's, it's a mix of both, right? It's like, I'm thinking very deeply about a writing problem that I have for cracking the code on this Kennedy chapter, or, or any of the chapters in the book. And then I'm working on it and I make some progress. Like I get words down,

• 1:23:43Ryan Holiday?

  I get it in order. And then I go for a run or a swim later in the afternoon. And then the real solution pops in my head. And I don't know if you can have one without the other.

• 1:23:53Rich Roll?

  I think it is both. I think it is both. Like Kennedy has to game theory every possible outcome and do these decision trees to figure out like what the, you know, what could possibly happen with anything that he does. But fundamentally, also,

• 1:24:09Rich Roll?

  These decisions need to be a function of, of, of a well honed intuition. And that's really developed through being able to be present with yourself.

• 1:24:19Ryan Holiday?

  And he goes swimming during the Cuban Missile Crisis. He, he writes a letter to-

• 1:24:23Rich Roll?

  Swimming, swimming's a big thing with a lot of people.

• 1:24:25Ryan Holiday?

  I think so. I think so. He's obsessed with water. I mean, he's a guy that grew up on the water, you know? But he, he writes a letter to the gardener from the White House, like thanking her because she helped.

• 1:24:35Rich Roll?

  The Rose Garden was a big-

• 1:24:36Ryan Holiday?

  Yeah, yeah. And, and I think, look, it's like-

• 1:24:40Rich Roll?

  Mister Rogers went swimming, which I did not know.

• 1:24:43Ryan Holiday?

  Oh, it's beautiful. It's beautiful. I, I want to go to the Pittsburgh Athletic Club where he swam. I just want to be in that space. But he, and have you seen the previews for the Tom Hanks movie?

• 1:24:52Rich Roll?

  I saw the trailer, yeah.

• 1:24:53Ryan Holiday?

  He swims in it.

• 1:24:53Rich Roll?

  Yeah, yeah, yeah.

• 1:24:55Ryan Holiday?

  But, uh, you know, I think from reading Eastern philosophy and maybe, look, there's parts that are missing from Stoicism that maybe they explain in length in other texts that were lost. But it's like, you almost get the sense from like Buddha or something. It's like, oh, so you're telling me I can solve like complex math theorems by just like sitting there and it pops into my head? Like, that's not, that's not true. But, and I know you had Cal on, I think it's, it's like, it's the, it's both. It's like working very intensely, eliminating distractions, doing the work. And then the solution pops in your head in the shower.

• 1:25:28Rich Roll?

  Yeah.

• 1:25:29Ryan Holiday?

  You know, like I think you need both.

• 1:25:32Rich Roll?

  How have you taken what you've learned from the process of writing this book? Like, how have you made changes in your own life? Like, what is it that you're struggling with the most where this has been helpful?

• 1:25:43Ryan Holiday?

  So like today was a good example, and I didn't do a good job of it, but it's like I had two podcasts. I had this and another podcast, I had thing in the morning. And then I had to drive here from Orange County and I had to check into my Airbnb in time. And I have this email that has to go out and I need my wife to like proof it. And then I wanted to get a run in and like all of a sudden I'm like- I'm like stressed out of my mind. I got like all these things and they all have to go right in the right order. And I was like writing in my journal. I was like, you know, I don't, I don't want to feel flustered today and I don't want to be short with people. Because none of this matters. Do you know what I mean? Like, like even like for it was hard for me to text you to say like, hey, could I come 30 minutes later?

• 1:26:27Ryan Holiday?

  And because like I, my instinct is like, oh, this white knuckle this. Do you know what I mean?

• 1:26:32Rich Roll?

  Yeah, like I got that and I was like, yes, no.

• 1:26:35Ryan Holiday?

  But my thing is like, I'll squeeze it all in. I'll just fucking squeeze it all in. And, and so part of that's part of letting go too. It's like, like this is all an illusion in my mind, like this, the pressure, nobody is actually saying like, I even scheduled, like I picked this. It's not even like, I'm not even like some actor where it's like the publicist put me on this tour, you know, like, but um, just realizing how much of the pressure I put on myself and how many of the times I force myself into situations that are going to make the end state that I want very unlikely. Um, so that's been a big one, you know, eliminating that amount of time I spend on devices,

• 1:27:16Ryan Holiday?

  eliminating the, the inputs that really make me unhappy has been, you know, or that, that challenge my stillness has been a big one. Having kids has probably been the primary, you'd think, I guess my thinking would have been like having kids will be chaotic and stressful and difficult. And so I'll have less, but it's actually been the exact opposite because there's such a good reminder of like what

• 1:27:44Ryan Holiday?

  you could actually be anytime if you choose to be.

• 1:27:46Rich Roll?

  Yeah. And what's really important? I mean, you talk about relationships in the book and any hard driving type A personality is prone to, you know, fantasies of what their life would be like if all, if every, all people went away. We could just do what we do and there'd be no obstacles.

• 1:28:03Ryan Holiday?

  Yes.

• 1:28:03Rich Roll?

  Or anybody else vying for our attention or our time. And, you know, that's one of the great illusions, I think. And as messy and as difficult and time consuming as relationships are, you know, you pointed out very point blank in the book, like, Yeah, but then there's no value in anything that you're doing.

• 1:28:21Ryan Holiday?

  Yeah, yeah, like there's this quote from Philip Roth that I found this he'd been married for a long time. Apparently it was like a horrible marriage because the woman wrote like this nasty memoir about it. But he was saying he was like, now that I'm single, he's like, all I can, all I have to focus on is my work. He's like, it's like there's always an emergency and I'm the patient or something like that. And I was like, that sounds horrible. Like the fact, like what my life would be if I was a hundred percent in charge of it and it was all about me would be so. I sometimes you think that's the fantasy. You go like, oh, that guy's single, he goes where he wants, he does whatever he wants, you know? And then you realize like, that fantasy is actually a fucking nightmare, you know?

• 1:29:03Ryan Holiday?

  Especially when you go through difficult stuff. It might be nice, you know, on a Tuesday, beautiful, you do whatever you want. You go for a two hour run instead of going like, I gotta be back here in forty five minutes or whatever. But, but what about when you get a cancer diagnosis? Or what if you, when you find out you're, I don't know, you're booked out, rejected or, you know, like, like the relationships are there for the, the hard times.

• 1:29:33Rich Roll?

  And also, if you're in the right relationships with the right people, these things float your boat. I mean, this is like an accelerator to everything that you imagined for your life.

• 1:29:44Ryan Holiday?

  Well, I've been saying that too, like, I think the generation before, maybe the couple of generations before, you know, that, that experienced so much pressure to have kids, like you have to have kids, you have to have them by this time. You know, woman's jobs to have kids, did a really good job making it clear that like, having kids is hard. And that, uh, you can't really have it all and there's a lot of sacrifices and, and it takes a lot out of you and all this stuff. And I think in the process kind of underplayed like.

• 1:30:19Ryan Holiday?

  What you get in the trade?

• 1:30:20Rich Roll?

  Mm hmm.

• 1:30:21Ryan Holiday?

  Do you know what I mean? And that like, it's like, like, um, who was it? There's some author and he was talking about how he's a great writer, like a very famous writer. And he was saying that someone came up to him and said, don't have kids. Every kid you have is a book you'll never write. And he was like, that haunted me. And he's like, now here I am, like, writing this. You know, I'm looking out at my like three sons. And I'm like, I'll take that trade any day of the week. Like, what? None of these books matter. You know, like, at the end of the day, none of these books matter. Um, none of the work we do matters, really. Like, it matters, but it doesn't matter. And the idea that like, you're not gonna have kids or you don't have time to get married

• 1:31:05Ryan Holiday?

  or be in a serious relationship with someone because like, the startup you're making is so important. It's just, it's just laughable if you look at it with any kind of distance.

• 1:31:15Rich Roll?

  The, the, the kind of flip reaction to that, though, is, oh, well, it's easy for you to say because you're successful, right? And it's in the sense that, oh, you can say that, you know, this like, this success isn't, you know, isn't all it's cracked up to be because you're secure.

• 1:31:32Ryan Holiday?

  Sure.

• 1:31:33Rich Roll?

  You know, in your trajectory. And I think there's a delusion that we may intellectually understand that, and yet we feel like it doesn't apply to us.

• 1:31:42Ryan Holiday?

  Sure. Although, like, when I think about it, I go like, I should have had kids earlier. Like, I, I, I don't go like, now I'm successful.

• 1:31:50Rich Roll?

  This goes back to my theory that you were born out of time.

• 1:31:52Ryan Holiday?

  Yeah. No, I just, I just think, I, I get that. And look, like, I also have help. You know, like, people are like, how do you balance it all? And it's like, I pay someone to help watch my kids. You know what I mean? Like, that's, and my wife doesn't have to go to an office every day because we have our own business. You know, like, I'm not saying that. What I'm saying is that, um, I get what they're saying. They go, it's easy for you to say you have it. At the same time, because I have it, I can tell you that, you know.

• 1:32:24Ryan Holiday?

  You think that writing a bestselling book or having a lot of money will make you feel good and that you'll feel whole. And that's the big lie that we all believe. And then it's like, the only moments where I really feel good, like my walk in the morning with my son, that's, that's what wholeness feels like. You know, hearing my, my book hit number one, it feels nice for like eight seconds, but it, it, that's a biological adaptation.

• 1:33:02Rich Roll?

  Hmm.

• 1:33:03Ryan Holiday?

  Where we go, hey, if we, if we cross that ocean, you know, if we kill those people and take what's theirs, then we'll be happy, you know, then I'll feel good about myself.

• 1:33:13Rich Roll?

  The unabated craving.

• 1:33:15Ryan Holiday?

  Yes.

• 1:33:16Rich Roll?

  That compels us.

• 1:33:17Ryan Holiday?

  And to go to the daddy issues, I think that like it's, I think for me, it was like, oh, like if I really get successful and it's, this is where my daddy issues is, but it's like, if I'm objectively successful and what I do is very impressive, then my parents will.

• 1:33:37Rich Roll?

  Right.

• 1:33:38Ryan Holiday?

  Give me what they should have given me at birth for being alive.

• 1:33:42Rich Roll?

  And how's that going?

• 1:33:43Ryan Holiday?

  It's a constant struggle, you know?

• 1:33:45Rich Roll?

  Yeah.

• 1:33:46Ryan Holiday?

  But, but I, I mean, one of the night, one of the nice parts of getting the stuff, it's nice that I got it.

• 1:33:50Rich Roll?

  Hmm.

• 1:33:51Ryan Holiday?

  But the, the blessing and the curse of it is you go, nope, still doesn't do it.

• 1:33:55Rich Roll?

  Yeah.

• 1:33:56Ryan Holiday?

  You know, it's like, and then it was nice for what I basically, it was freeing to go like, all right, and maybe some, and some people don't get this gift, but it's going like, all right, this doesn't impress these people, nothing will, and I can stop trying, I can stop doing these things to get that.

• 1:34:12Rich Roll?

  There's a relief in that. Yeah. Well, one of the tools that you talk about in the book for, for navigating this, which I love, is this idea of like holding on loosely.

• 1:34:21Ryan Holiday?

  Yeah.

• 1:34:22Rich Roll?

  Right? Like not, not, you know, if you're like a hard charging person and you've got these goals and you're just like, ah. I'm gonna make this happen and you're just full of self-will. Chances are like, there's gonna be problems with you. And the people who can kind of release their grasp on it, hold it a little bit, you know, less tight, be open to, you know, dips and turns along the way, are the people who ultimately end up in a better place.

• 1:34:52Ryan Holiday?

  Yeah, it's like, you go to a driving range one time and you get this proven to you pretty quickly. It's like, the harder you try to hit a golf ball, not only the less far does it go, but like, the worse the shot is. And the idea that that's not true in life, which is much harder than golf, is ridiculous.

• 1:35:13Rich Roll?

  Yeah, I was just in Montana a couple of days ago for this event. It was like this gathering, a bunch of cool athletes and people were there. And I had an opportunity to do a live podcast with this woman, Gwen Jorgensen, who won the Olympic gold medal in triathlon in the last Olympics and was dominant in her sport for a long time. And now she's making the transition to marathon running, which is super ballsy. Like, it's a great story. But what this holding on loosely thing reminded me, or just made me think about this conversation, was that she started out as a swimmer. She swam at the University of Wisconsin and she kind of rode the bench. Like, she wasn't that great.

• 1:35:54Ryan Holiday?

  That'd be a bad place to swim.

• 1:35:56Rich Roll?

  She was not, why?

• 1:35:57Ryan Holiday?

  Because it's so cold.

• 1:35:58Rich Roll?

  Well, you're indoors. You swim indoors all the time.

• 1:36:00Ryan Holiday?

  But just the pro, like, it's like, I'd rather swim in a warm place. Like, just the waking up early, going out in the cold, like, better be a swimmer in a place where it doesn't snow, is what I'm saying.

• 1:36:10Rich Roll?

  Well, I'm with you on that. But, you know, she grew up as a kid, like, holding on very tightly to this idea that she wanted to be an elite swimmer, an Olympic swimmer, and wrote her gold times on her ceiling and like, the whole deal, right? And meanwhile, like, every once in a while, she'd go out and run. And she was this, like, incredibly gifted runner.

• 1:36:31Ryan Holiday?

  Yeah.

• 1:36:31Rich Roll?

  And to the point where people were like, hey, you should really think about, like, running track. And she'd be like, no, I'm a swimmer. Like, she held on so tightly to this idea, this identity that she had crafted about who she was, that she couldn't see this other potential avenue for herself. And I think it short-circuited her. I mean, eventually, it was inevitable. She, she like, made the switch to track and she couldn't even qualify for NCT 2A's in swimming. And like, within a year, You know, like being brand new to this sport, she immediately is like, you know, she's like Big Ten champion and like the rest is history. But I wonder like, had she held a little bit more loosely?

• 1:37:09Ryan Holiday?

  Yeah.

• 1:37:09Rich Roll?

  Perhaps she would have realized that much sooner.

• 1:37:12Ryan Holiday?

  Isn't that Lance Armstrong's story too? He was a triathlete and then it was like, oh, you're way better at biking than the other things. Like, and I think it's very, I mean, I love David Epstein's book on range.

• 1:37:21Rich Roll?

  Right.

• 1:37:21Ryan Holiday?

  Where it was like, oh, it's the problem is that they told Tiger Woods he was a golfer and that all of his identity was in being a golfer. Paul Graham has this amazing essay called Keep Your Identity Small. So it's like, if you see yourself as a Republican, it's hard for you to change your mind when you, it's hard for you to see an issue objectively, because you're looking at it from the lens of my identity as a Republican and you don't want to, you don't want, even though you actually think X, that contradicts your identity as a Republican. So you think about it differently. And he says something like, the more labels you put on yourself, the stupid, the stupider you are. Because now all of a sudden you've limited what your options are.

• 1:38:00Rich Roll?

  Constructed this sense of who you are.

• 1:38:02Ryan Holiday?

  Yeah.

• 1:38:03Rich Roll?

  The story that you tell.

• 1:38:04Ryan Holiday?

  Yeah. And, and, and so I think this ties into the inner child thing too, where it's like, so if your thing is like, I gotta impress mom and dad. And what are the things that impress mom and dad? You're already, you've already closed yourself off to all, like, maybe mom and dad don't, mom and dad respect doctors, but like, you're actually put here to be a guitar player.

• 1:38:24Rich Roll?

  Yeah.

• 1:38:25Ryan Holiday?

  And so how many amazing talents get squandered because, you know, your mom and dad are going to find a way. If your mom and dad have made you being a doctor, uh, part and parcel of them loving you, they're going to find a way to not love you, even when you're the world's best doctor. You know what I mean? Like, they're gonna, they're gonna go like, oh, you work here, or you know, or they're gonna be like.

• 1:38:48Rich Roll?

  That's like a Neil Strauss tweet.

• 1:38:49Ryan Holiday?

  Yeah.

• 1:38:52Ryan Holiday?

  But I think it's true. Do you know what I mean? Like if you, if you, they're just in the way that we move the goalposts on ourselves. So are they?

• 1:39:00Rich Roll?

  Right.

• 1:39:01Ryan Holiday?

  Cause that's what we do.

• 1:39:02Rich Roll?

  Have you found, what, what's the biggest, like, have you changed course on any long held ideas that you've had? Like, have you had changes of heart or like, wow, I always thought this was this way. And as a result of all this work and research and deep thinking that I've done on these subjects, I'm changing my mind on this.

• 1:39:21Ryan Holiday?

  I mean, I do like changing my mind. I don't know if I have like some like great example or like I switched from, you know, this to that. But, um, yeah, I don't, I don't know if I have one, but I think that is a good, a great question is like, where, where do you change your mind? Have you changed your mind recently? Um, I think a big one for me is just like going like, I, I need to like, not care less, but like, I have wrapped a chunk of my identity up around like, knowing a lot about a lot of things and having interesting opinions about them. I'm like trying to get more comfortable with being like, I don't, I'd never heard of that. But yeah, I don't know what's happening there.

• 1:40:05Rich Roll?

  Right.

• 1:40:05Ryan Holiday?

  Sure. You're right. You know, like, like, just like.

• 1:40:08Rich Roll?

  Instead of being the guy who always is like, oh yeah, I read a book about that.

• 1:40:12Ryan Holiday?

  Yeah. Yeah. Or just like, like, oh, let me tell you why you're wrong about this. Like, it's like, can I, can I, like Marcus really says, he's like, you know, it's possible to not have an opinion about things. Like, like you could just not have an opinion. That is possible.

• 1:40:24Rich Roll?

  Yeah.

• 1:40:25Ryan Holiday?

  It feels unnatural.

• 1:40:28Rich Roll?

  Well, we're in this, you know, back to the current culture. Like we, we've, you know, calcified our ability to be nimble with ideas. And, you know, we're expected to toe a certain line and have an opinion on everything. And I think it entrenches these narratives and it's splitting us apart. And it's, it's, it's eroding the fabric of our culture and our, and our ability to have productive conversations.

• 1:40:52Ryan Holiday?

  Yes. Yeah. No, the radicalization of one side radicalizes the other side. And then it just.

• 1:40:58Rich Roll?

  And there's, there's, there's, you know, there's a lot of energy. Behind preventing you from changing your mind on anything.

• 1:41:07Ryan Holiday?

  Yeah.

• 1:41:07Rich Roll?

  Because the risk of stepping outside of whatever doctrine you know, you're sort of associated with is become suddenly very high.

• 1:41:15Ryan Holiday?

  Right. So it's like what they're trying to do is take away your ability to think about this and trying to to sort of put blinders on you and ratchet up the stakes artificially and make it impossible for us to like come to any kind of compromise or solution or you know what I mean? They're like, you can't, you can't have an opinion about this. You can only have this party line.

• 1:41:38Rich Roll?

  And, and to adopt a contrary opinion is to face ostracization.

• 1:41:43Ryan Holiday?

  Yes.

• 1:41:44Rich Roll?

  You know?

• 1:41:44Ryan Holiday?

  Sure.

• 1:41:46Rich Roll?

  It, it, it goes to, you talk about this in the book too, like the information diet, right? I didn't realize like Thich Nhat Hanh had spoken about.

• 1:41:54Ryan Holiday?

  Yeah. I think he was actually probably more talking about what you talk about that. I think he was, I think if I remember that quote correctly, he's talking mostly about food. But, uh, you know, it's like, look, if you're putting like poison, basically industrial agriculture in your body.

• 1:42:09Rich Roll?

  Yeah.

• 1:42:10Ryan Holiday?

  Garbage is going to come out both like literally and figuratively. But I think it's, it's just as true for information. If you are mainlining the constant chattering of, of manipulative, you know, people who profit from your rage, the idea that like peace and stillness and clarity and compassion goodness is going to come out of that. It's delusional.

• 1:42:36Rich Roll?

  Yeah. The opportunity cost. I mean, the, this willingness that you have to have to not be fully informed all the time. Like there's this compulsion that so many of us have that we need to be up to date on everything all the time and have an opinion so that if we meet somebody, we can say the right thing or whatever. And the truth is the opportunity cost of that is that you deprive yourself of, of that ability to think deeply about what's most important. And you have to be willing to be like, no, I hadn't heard about that, or I don't know about that, or I, I didn't see that. I didn't watch the debate. I didn't see the latest movie or whatever it is.

• 1:43:10Ryan Holiday?

  Yeah. Yeah. Yeah. And, and it's, it's a.

• 1:43:14Ryan Holiday?

  That's that that feels like a like you're being it's like a dereliction of duty. But it's like, actually, your duty is to go read a history book and understand where this all fits in. You know what I mean? Your duty is not to follow trivia in real time. Like, and also, there's a humility. I've I started saying this. It's like, smart people are on that. Like, like, we have our people on that. You know what I mean? They don't necess- I'm not the savior that should that's gonna ride in and save that issue. There are things where I might be able to do that.

• 1:43:48Rich Roll?

  You don't need to have an opinion and voice your opinion on everything on Twitter.

• 1:43:52Ryan Holiday?

  Yes, yes. Like, I think the the mass the two mass shootings that happened, I mean, this will go later, but like, two mass shootings, it's like, not they don't need me to condemn this. It's objectively wrong. Like, you know what I mean? Like, it that's

• 1:44:09Rich Roll?

  Do you feel that pull, though, as somebody with an audience? Like, when something like that happens and I and I open up Twitter and I look at what's going on, I feel like, do I need to say something? And I'm like, I don't, I don't

• 1:44:20Ryan Holiday?

  I think the ego is in the like, my eye, like, I'm I'm gonna move the needle on this one. Like, like, look, if you're if you're, you know,

• 1:44:29Rich Roll?

  Because you you have to square that with like, silence is, you know, if you're silent about things that are wrong in our culture, like, you're complicit.

• 1:44:37Ryan Holiday?

  Right. But it's like, I'm not silent talking to, I mean, I'm not talking to my two year old about it, but I'm not gonna, if if I had a teenager, I wouldn't be silent about it. Do you know what I mean? I would, I would not be silent about it where I have like, real impact. Where I, so it's an interesting thing, because I'll write, I I feel like my job is to write, is to apply sort of ancient wisdom in history to modern life. So I'll write something. I wrote an email on Monday for Daily Stoic, which is like this email that goes out to people. And and and I wrote a thing about

• 1:45:13Ryan Holiday?

  Marcus Aurelius and Seneca were both two real world politicians who dealt with like actual tyrants and murderous dictators, right? And, and so they were talking about, you know, what it's like to actually be these people, you know, like Seneca was in Nero's court, like worse than Donald Trump by a factor of a hundred, right? And he's talking about, you know, like what these people are like and what it's like to be them. And so I was writing a thing about how like nobody, like people are like, what should I tell my children about Donald Trump? And they think it's like, you know, these lessons about the specific policies when it really should be about like, it should be like, kid, this is what it's like to be a horrible person. This like, you know what? This is what it does to you.

• 1:45:58Ryan Holiday?

  And character matters and that you don't need to talk to them about the fact that he was, you know, he said you should grab women by the pussy. I mean, you, you do in that you teach your kids like what boundaries are and what respect is, but it's more like you don't need to talk to them about the word choice of pussy. You need to talk to them about character, right? And so I send out this email. I think it's very well reasoned. It's deliberately non-partisan. Um, I'm a center right person, but then I watch all the people unsubscribe, you know? And my point, they always send me, why did you do this? I love you. I love your writing. You shouldn't be partisan. And like what I say is like, my job is to say what I think and what's important and what I think the facts support in the context with which I do my work.

• 1:46:43Ryan Holiday?

  And what I don't do is think about what the financial repercussions for doing that are. Does that make sense?

• 1:46:51Rich Roll?

  Yeah, it goes back, I mean, it's a predominant theme in your book, which is basically learning how to hone your instincts and your intuition. And through that process matched with deep thought to, you know, express a cogent informed opinion that is liberated from the external ramifications of, of, you know, putting that out into the world.

• 1:47:11Ryan Holiday?

  Yeah, you like Marx realist science is just do the right thing. The rest doesn't matter. And so it's like, I thought that was the right thing to write creatively, uh, you know, politically, philosophically. And so if, if, you know, 500 people who I worked very hard to bring into the universe left because of that, like, whatever. Life is way too short to not say what I think, to keep people whose opinions I don't respect, you know, following my work. And life is also too short to be upset by that, or you know what I mean? And so you just, you say what you say. I don't think it's, I'm not saying it's courage, but it's, it's like your obligation as an artist

• 1:47:55Ryan Holiday?

  is to speak truth as you see it. Your art, your, it's not to change the world. You know, your, your job is to speak truth. Whether that truth ends up changing the world is one thing, but.

• 1:48:07Rich Roll?

  Yeah. It, it goes to this idea of virtue not being an abstraction, but in action.

• 1:48:13Ryan Holiday?

  Mm hmm. Absolutely.

• 1:48:15Rich Roll?

  Yeah. It was interesting to read about how Seneca became, he became a victim of, you know, basically being power hungry under Nero, right? Like, so he, despite all of his incredible wisdom, he still couldn't, um, he still couldn't walk that line of virtue to distance himself from this terrible person.

• 1:48:38Ryan Holiday?

  And that's what I think.

• 1:48:38Rich Roll?

  His own fortune was too closely tied to it.

• 1:48:41Ryan Holiday?

  Yeah. And, and I think, yeah, it's like he, the Stoics over and over, virtue is enough. Virtue is sufficient. What's right is doing the right thing. And here you have this guy making compromises. Probably, I mean, and, and I've, I've been there because I've worked for people, not nearly as bad as you know, but I've worked with people that, you know, certainly in retrospect, certainly getting older, but even at the time you have ethical concerns about. And you're like, but if I don't do this, what, there's two, there's the savior, savior conflicts. I don't do this, a worse person is going to take my job, take this job. And then, you know, like, so it's, I gotta do this. And then the other is like, but this is my shot.

• 1:49:24Rich Roll?

  Yeah. Well, yeah, when you're young too, it's harder to.

• 1:49:27Ryan Holiday?

  But I think like, so I, there's a couple Republican senators who've, who read the Daily Stoic and one of the weird, even weirder than the sports team is like, a couple of times they've had me to the Senate dining room, uh, to have breakfast and like talk about philosophy, which is just like unreal. They're not people.

• 1:49:43Rich Roll?

  You're having your own kind of like Seneca experience.

• 1:49:46Ryan Holiday?

  Well, I wrote, I wrote a New York Times piece about that because I actually got. Offered a press secretary position for one of the cabinet members.

• 1:49:54Rich Roll?

  I didn't know that.

• 1:49:55Ryan Holiday?

  I'll send it to you. And I surprised myself by even thinking about it. I mean, this is in early, late 2016. There's a moment where it seemed a little less crazy than it does now. But anyways, I was so I'm there talking philosophy to these guys and, and you know, they, they, they pointed, I was like, why aren't people stopping this? You know, like, it seems so obvious. And, and one of them said, like, um, see that guy over there? You know, if he hadn't said what he said about Trump, Trump probably would have named him like, I don't know, head of the CIA or something like that. And so to them, the lesson was like, you know, by criticizing, you're depriving yourself of a

• 1:50:40Ryan Holiday?

  position to affect the change you've worked for your whole life, the principles you honestly believe in, or maybe just to stop Trump from doing something stupid, right? But to me, the philosophical, and I think that's what Seneca tells himself, working for Nero. If I'm not Nero's tutor, who's, he's not going to have one, right? If I'm not advising him, he'll do even worse things. But the problem is, it's like, do you actually want to be director of the CIA for this administration? Are you actually doing, like, is that what you worked your whole life to get?

• 1:51:12Rich Roll?

  And when you have that position, are you actually going to follow your moral compass? Or is there going to be another, you know, compromise that's going to compel you to pull a party line that's at odds with your true nature?

• 1:51:24Ryan Holiday?

  Yeah. And so it's like, so Seneca writes all this stuff about philosophy and then he ends up having to help Nero justify why he had tried to have his mother assassinated. You're just like, that's how quickly it escalates.

• 1:51:37Rich Roll?

  And rationalizing it.

• 1:51:39Ryan Holiday?

  And rationalizing it. And, and yeah, like, I don't, I, and he only realizes too late what he's got himself into. And he tries, he basically what, what this is, and this is where it's really insidious is Nero is just piling money on top of Seneca. Like, Seneca becomes like the second richest man in Rome. And so obviously that was interesting and fun and he talks about it philosophically, but you're just like. He, he, at some point Seneca goes like, oh, this is bad. Like, what have I gotten myself into? I gotta get out of here. And he goes to Nero and he says, I want out. And it's sort of like a blood in, blood out situation. It's like, you don't get to leave.

• 1:52:20Rich Roll?

  Yeah.

• 1:52:21Ryan Holiday?

  What the fuck are you talking about?

• 1:52:21Rich Roll?

  Like the mafia.

• 1:52:22Ryan Holiday?

  Yeah. And then Seneca goes, I'll give you all the money back. And Nero says, no, no, no, no, no. And, and he's like, I'll let you partially retire. And, and so Seneca gets that. And, and then Nero goes, I don't like Seneca anymore. And he executes him, basically. And so that, Seneca realizes too little, too late. This is probably when he's writing some of these essays, like the essay that opens the book. I think he realizes, he never comes out and says it, but I think he realizes that it was a Faustian bargain. And then he sold his soul to the devil and.

• 1:53:01Rich Roll?

  Classic Faustian.

• 1:53:03Ryan Holiday?

  Yeah.

• 1:53:03Rich Roll?

  Like textbook.

• 1:53:04Ryan Holiday?

  Yes.

• 1:53:04Rich Roll?

  You know?

• 1:53:05Ryan Holiday?

  Yes.

• 1:53:07Rich Roll?

  And then we see this playing out in real time.

• 1:53:09Ryan Holiday?

  Yeah. I mean, like, I, I have so much respect for someone like, um, General Mattis. And it's so admirable that he resigned on principle over, we don't really know what it was, but he basically resigned over principle. And it shocks Trump, right? Like, but at the same time, maybe the real principle is like, no. You know, like, how many, how, how, how much did the idea that people like James Mattis were going to be in the administration? Allow other people to rationalize voting for it? Supporting it? Not, you know, doing some of the things we're doing now earlier, right?

• 1:53:49Ryan Holiday?

  So it's like, it's one man's, uh, valiant sacrifice is a, by another definition, complicity.

• 1:53:58Rich Roll?

  Yeah. Yeah. Super interesting.

• 1:54:01Ryan Holiday?

  And these are timeless ethical quandaries.

• 1:54:04Rich Roll?

  Right. Yeah. I mean, this, that's why it keeps, it comes up time and time again. And what, you know, what is ancient is, is modern.

• 1:54:10Ryan Holiday?

  Aristotle is Alexander the Great's philosophy instructor. Do you know what I mean? Like, it, it, we tend to think that all these things were clean, but like, it's so complicated. Confucius was a, was not just a philosopher. He worked for these princes and kings, like these, that, that, studying the eastern stuff, you realize that these people were much more of the world. Than they seemed. And sometimes they did horrible things. I mean, Buddha had a wife and child that he walked out on.

• 1:54:38Rich Roll?

  Yeah.

• 1:54:39Ryan Holiday?

  Which I found, you know, very hard to square.

• 1:54:43Rich Roll?

  And, and the issues with Leonardo da Vinci and his dad and like, you know, how he's just trying to find these benefactors. And it's like, you just, because you don't think of him as a human being.

• 1:54:53Ryan Holiday?

  Yes. Right. Yeah. I, I did you relate to, I've related to you so much.

• 1:55:00Rich Roll?

  Yeah, in many ways.

• 1:55:01Ryan Holiday?

  Yes.

• 1:55:01Rich Roll?

  Um, well, let's talk about the body section. Um, you, you've pulled this hat trick again, which you've done a number of times, which is essentially you're, you're kind of writing a self-help book without writing a self-help book. You never kind of come out and give any prescriptive advice. I would say this section is the most prescriptive of anything you've ever written. You're kind of like, look, you should journal, like, look at these other, you list like 20 people in a row, all these amazing people. Look, they journal every day, like, go on walks, like, you know, take this time, like, yeah, sleep, like, this is very, this is back to like practicality.

• 1:55:35Ryan Holiday?

  Yeah. Well, it's because it's, it's hard to go like, do this thing with your mind, because that's not how the mind works. But you can go like, go for a walk, here are the benefits of walking, or you can say like, here are the costs of sleeping. Like, I can, even though I wasn't there, if you're, the Arianna Huffington tells a story of like, brushing her teeth in the bathroom, basically, and passing out, and her cheek hitting the bathtub on the way down and shat, like, I can hear that noise.

• 1:56:06Rich Roll?

  She told that story on the podcast.

• 1:56:08Ryan Holiday?

  It's, it's, it makes you so uncomfortable. Do you know what I mean?

• 1:56:14Rich Roll?

  And the solutions are so basic.

• 1:56:17Ryan Holiday?

  Yeah, go to sleep.

• 1:56:18Rich Roll?

  Yeah, go to sleep, take a walk. Here's one question I had for you, though. When I'm reading the, the take a walk section, and you're naming all these people, I'm like, where's David Sedaris? And then you bring him up in the hobby section, but I'm like, I wanted you to go deeper into his like garbage collection thing, because like, that's like weird and I think obsessive compulsive on his part, because like, he can't miss a day. And he's, he goes out and walks like 20 miles and he picks up every piece of garbage in his entire town.

• 1:56:47Ryan Holiday?

  He won like an award for like.

• 1:56:48Rich Roll?

  I know the queen, the queen gave him like a thing.

• 1:56:50Ryan Holiday?

  I started doing it.

• 1:56:51Rich Roll?

  You did?

• 1:56:52Ryan Holiday?

  Yeah. I were, I live on, I spent a lot of time on the, our farm is on this dirt road and like, my neighbors are basically animals. I shouldn't say this, but I was like. You know, they're just like, oh, I've finished with this, I'm gonna throw it out the window. And it's not maintained by the city. So like, or the county. So if I don't do it. And it's, I don't know, like, it's actually wonderful, like.

• 1:57:12Rich Roll?

  You pick up like a mattress the other day or something.

• 1:57:14Ryan Holiday?

  Pick up a mattress, yeah.

• 1:57:17Ryan Holiday?

  But like, my son will now, he's two and a half, he'll point out garbage and say, like, pick it up. You know, like, so I, to me, it's meaningful. And I'm already walking. And, I don't know.

• 1:57:32Ryan Holiday?

  It's like, instead of having a strong opinion about whether restaurants should be allowed to have straws. Like, why don't we just pick up trash when we see it?

• 1:57:40Rich Roll?

  Yeah.

• 1:57:40Ryan Holiday?

  You know, but it, I just love, I put it in the hobby section because it's a weird hobby.

• 1:57:44Rich Roll?

  Yeah, yeah, yeah. But I, but the relationship between, I've thought about this a lot. Like, what is the relationship between that practice and his creative inspiration? Because there's something about that, you know, low heart rate, you know, kind of activity that creates space for those little sparks.

• 1:58:02Ryan Holiday?

  I think it's probably better for fiction than nonfiction. Although his stories are sort of a mix of both.

• 1:58:09Rich Roll?

  He goes out like all day.

• 1:58:10Ryan Holiday?

  But I just mean, like, I, I think it's about, yeah, slowing the mind down. And then these funny things are popping up to you. And then you go, I think my uneducated opinion is that maybe fiction is a little bit more like,

• 1:58:25Ryan Holiday?

  you do a lot of that and then you sit down and it pours out. Whereas like, to me, nonfiction is, it's much more a construction of an argument. So I think it's more, it's, do you know what I'm saying?

• 1:58:38Rich Roll?

  Yeah, I see what you're saying, but I don't, I don't know if that.

• 1:58:41Ryan Holiday?

  So I think that's why he does it for six hours.

• 1:58:44Rich Roll?

  Yeah, well, I think there's like a mental tweak there with him. I mean, you could also, you could have also put that in the routine section. Because that's very much his routine.

• 1:58:53Ryan Holiday?

  And they're, yeah, they're all related. The writing is part of my routine. It's what I do before I do X, Y, and Z.

• 1:59:00Ryan Holiday?

  And and like, again, I think going for a long walk might get you seventy percent of what meditation gives you, you know, or something like, let's say it's my, the point of my book is like, okay, med meditation is great. And let's say it's this, it's everything that we're told that it is. But for some reason, we're not doing it. Like analogy, you do you know, Ramit Sethi is the personal finance.

• 1:59:23Rich Roll?

  I know he is, yeah.

• 1:59:24Ryan Holiday?

  He's like, look, people don't keep budgets. Like, you can write a budget, but you won't keep it. So I'm not going to tell you to do it. But I am going to tell you to like, set up these auto transfers in your bank account. And then it takes that out of it. So my point is like, uh, I could tell you to meditate, and I know I should meditate, but I'm not gonna, I'm just knowing myself. So like, I will take a walk and I'll, I'll eighty twenty it, you know, I'll get a chunk of it.

• 1:59:48Rich Roll?

  The walk takes a lot longer.

• 1:59:50Ryan Holiday?

  It does, does.

• 1:59:51Rich Roll?

  And you're willing to do that, but not meditate.

• 1:59:54Ryan Holiday?

  Yeah, yeah, yeah.

• 1:59:55Rich Roll?

  It's interesting, right?

• 1:59:56Ryan Holiday?

  Yeah. Or swim, I mean, to me, swimming is the

• 1:59:59Rich Roll?

  Yeah.

• 2:00:00Ryan Holiday?

  Swimming is the best one.

• 2:00:02Rich Roll?

  There's something about swimming that's like a pipe cleaner for your mind.

• 2:00:07Ryan Holiday?

  Well, I think it's immersive. My, my theory is totally immersive. So it has a sensory deprivation component. I think there's something womb like about swimming that our bodies just respond to on a prime level. No screens. Uh, you're looking down. So you're, it's all, you're not really seeing anything. I think there's something about cold. Like I'm much, I get much more out of swimming in a cold pool than like when it's hot. Um, and then there's something about the forcing yourself to do something that at first you don't want to do. Then there's, you know, then the endorphin, all, all of it. I think, and I just think there's something magical about water that like all, all cultures seem to have created fountains.

• 2:00:55Ryan Holiday?

  Do you know what I mean? Like there's Roman fountains and there's Buddhist fountains and there are, you know?

• 2:01:02Rich Roll?

  So, yeah, so you're drawing like the calming effect of like seeing water move. But that's different from the immersion. Like, I would agree with you. There's something that happens in swimming that I don't like. Running is amazing and it serves lots of these similar kind of, you know, agendas, but there's something distinct about swimming. That's its own unique thing.

• 2:01:24Ryan Holiday?

  Like Barton Springs where you and I swim and awesome, where I like to swim the most when I can, like for like 500 years, dating back at least basically till we do, that was a day, like Indians used to go there, like we had, like Native Americans also saw it as a sacred place. Do you know what I mean? And would swim in it and use it and be around it. And so it's like every culture has this strange relationship with water. Some, some spiritual, someone told me it's because we're mostly water.

• 2:01:57Rich Roll?

  Maybe that's it.

• 2:01:58Ryan Holiday?

  That there's some, you know what I mean?

• 2:01:59Rich Roll?

  You should have put that in the, in the spirit section of the book.

• 2:02:02Ryan Holiday?

  Yeah.

• 2:02:04Rich Roll?

  On the routines thing, one of the things that I liked is that, you know, now we're in, everybody wants to know everybody's morning routine and the whole, you know, it's like, oh, if I just do exactly what Stanley McChrystal does, then I'm going to, you know, be this person or whatever. And, and you don't really kind of say it, say it expressly, but the point is more just have one. Like you show all these people, they all their, their routines are wildly different, but they have a routine and they're disciplined about it. And, you know, what serves one person is going to be different from what serves another. And it's about, you know, look, if you can be still enough to then figure out like, what is going to be the one for you? And then adhere to that, like you don't need to get up at 4:30 and take a picture of your watch, like Jaco Willink.

• 2:02:48Rich Roll?

  And if you do, more power to you, but that's not for everybody.

• 2:02:52Ryan Holiday?

  Yeah, no, I'm actually, it's like, I think there's a danger in some of those like sort of books about routines, because people think that it's like, in the same way they go, oh, 10,000 hours? Okay, just did one hour, just did another hour. It's not that. It's, it's like anything becomes sacred if you treat it right.

• 2:03:10Ryan Holiday?

  And you do it enough, you know, and, and so it's not about what other people's routines are. It's about yours. And the other, the thing I've learned since having kids and, you know, the fact that I have a pretty rigorous travel schedule for my work is it's like, actually, it's routines plural. Like I have, I have a travel routine. I have the day, the kids go to daycare routine, the day, the weekend routine, you know what I mean? And it's, and, and the ability to go like, today I'm switching to this routine. So that like it's, there's a, there's also an ego. And then maybe this is why people think they can't have relationships is going like, this is what I do every day. You're getting in the way of the routine.

• 2:03:51Ryan Holiday?

  I gotta, I gotta stick with that thing. To me, the ability to go like, sometimes I do this, sometimes I do this. But it's like, when, it's like, if A, then B, if B, then C, you know, like having, having different routines, I can sort of effortlessly choose based on circumstances. Not only, it allows me to be less rigid and less existentially anxious if, if the conditions are not perfect.

• 2:04:20Rich Roll?

  Yeah, because we live in the world and that rigidity is going to create all kinds of anxiety and issues because life has a way of intervening, you know, it's like, no matter how well intentioned you are and how many boundaries you erect to protect whatever routine you have, like stuff happens, man. And if you're gonna freak out and your whole life is gonna turn upside down because you didn't get to, you know, do the one thing, you know, write in your journal or whatever, then that's at cross purposes with the entire intention behind the entire, the whole thing.

• 2:04:48Ryan Holiday?

  Yeah, I'd be constantly trying to get in Russell Westbrook's head and mess up his routine. Do you know what I mean? I'd be like, what could you do to get inside that loop in that guy's head?

• 2:04:58Rich Roll?

  Right. Cause that, then it's a house of cards.

• 2:05:00Ryan Holiday?

  Yes.

• 2:05:01Rich Roll?

  Right?

• 2:05:01Ryan Holiday?

  Yeah.

• 2:05:02Rich Roll?

  So I want to round this out.

• 2:05:04Ryan Holiday?

  Okay.

• 2:05:04Rich Roll?

  And, and end it in a minute, but I want to, I want to like, um, do that by talking about. Service, which kind of brings it back to the 12 steps, right?

• 2:05:15Ryan Holiday?

  Yes.

• 2:05:16Rich Roll?

  Like, like

• 2:05:16Ryan Holiday?

  The underrated little one step.

• 2:05:19Rich Roll?

  What divinely inspired.

• 2:05:20Ryan Holiday?

  Yeah.

• 2:05:21Rich Roll?

  My primary purpose is to stay sober and help another alcoholic. Like, my job is to be of service. And the more that I can inject, not just in that formal construct, but everything that I do, if I can, if I can come from a service perspective and enter situations from, um, from a position of, of what can I contribute? And how can I enhance somebody else's life? Rather than like, what am I going to extract out of this to benefit myself?

• 2:05:49Ryan Holiday?

  Sure, sure.

• 2:05:51Rich Roll?

  My life goes better, you know? And that's, you know, something that you explore in the, in the book as well. Like, how can, how can we be like, part of this whole equation of being still is about giving?

• 2:06:03Ryan Holiday?

  Yeah. And, and one way to think less about yourself is just to like, think more about other people. You know what I mean?

• 2:06:08Rich Roll?

  Because self obsession is the enemy of stillness, right?

• 2:06:11Ryan Holiday?

  Yes.

• 2:06:11Rich Roll?

  And the, the path out of self obsession is to avail yourself to another.

• 2:06:16Ryan Holiday?

  Yes. Then, did you read the new David Brooks book, The Second Mountain?

• 2:06:20Rich Roll?

  No, not yet.

• 2:06:21Ryan Holiday?

  It's really good.

• 2:06:21Rich Roll?

  I've listened to some interviews with him recently though, and it's pretty amazing. It's pretty fascinating.

• 2:06:25Ryan Holiday?

  Yeah, I think that it's like, oh, because what happens is you climb the first mountain, which is success, getting what you want. And you realize it's nice, but it's not actually what you want. What you want is connection and to be of value to people and to be a part of a community and to do things that matter, you know? And I think people think you have to do this on this grand scale, but it's, you know, maybe it's just like, I don't know, being like a dad's my number one priority. Or something like, I think just, just getting out of your own head a little bit, getting, not making your ambition the primary driving force in your life.

• 2:07:07Rich Roll?

  Being a little bit more like Fred Rogers.

• 2:07:10Ryan Holiday?

  Yeah, what a, what a human being, right?

• 2:07:11Rich Roll?

  Yeah.

• 2:07:12Ryan Holiday?

  Maybe you should be a saint. I wonder if that'll, I wonder if 500 years from now, we have a little distance, that can happen.

• 2:07:18Rich Roll?

  It would be cool.

• 2:07:19Ryan Holiday?

  Although I guess he wasn't Catholic, so maybe you can't do that.

• 2:07:22Rich Roll?

  Well, a different kind of saint, perhaps.

• 2:07:24Ryan Holiday?

  Even a secular saint.

• 2:07:25Rich Roll?

  Certainly, somebody who's, who carried a very high consciousness.

• 2:07:30Ryan Holiday?

  Yes. Yes.

• 2:07:32Rich Roll?

  I'd never thought about the, the flashing yellow light.

• 2:07:35Ryan Holiday?

  Yeah.

• 2:07:36Rich Roll?

  Explain that a little bit.

• 2:07:37Ryan Holiday?

  Well, so if you, if you watch Mr. Rogers, you, people remember the singing, they remember the sweatshirt, or the sweater and the shoes and the train. But the first thing that you see when the show starts is actually a flashing yellow traffic light. Not like a yellow light, like it's about to turn red. It's the warning, like railroad tracks ahead, be careful, slow down, hazardous road. And that's like a powerful symbol. And then when you think about what the show is, the show is all about slowing down.

• 2:08:09Rich Roll?

  Right.

• 2:08:10Ryan Holiday?

  His tone is slow.

• 2:08:11Rich Roll?

  So deliberately slow.

• 2:08:12Ryan Holiday?

  Yes, almost uncomfortably slow. And then you realize it's like, oh, because I'm not the audience. The audience is a child who's never heard any of these basic things before. And, and it's, it, I, there's a scene, he talks about where he's like, the first time I turned on a television, I didn't know what it was. And there were these people throwing pies at each other. You know, he was like, they were throwing pies at each other. It's like magical technology and we were using it to do that. And I think his point was like, what if we use this to give the world more of what it needs, not more of what it doesn't need? And that was his mission, you know?

• 2:08:54Ryan Holiday?

  No one gets into children's tele, well, I guess some people do now in Nickelodeon or whatever. But you know, one gets into children's public access television to get rich.

• 2:09:02Rich Roll?

  Right.

• 2:09:04Ryan Holiday?

  And that's something I talk to authors about why. And it's like,

• 2:09:09Ryan Holiday?

  If if you're you're like, because people go, I would like you to write a book with me or write a book for me or market my book. And I go like, what are your goals? What are you trying to do? They're like, you know, my number one goal is to be a New York Times bestseller. Number one goal is to sell 2 million copies. Whenever I hear a number of copies that people want to sell, I'm like, nope, goodbye.

• 2:09:27Rich Roll?

  But no mention of the idea that they want to birth into the world.

• 2:09:31Ryan Holiday?

  Yes, but which is problematic in itself. But I go like, if your thing is to make money, you you already fucked up. Like, this is the worst way to make money. Like, this is the worst way. But, you know, it's like, you're selling something that takes you're selling something people to people that they actively don't want, which is really, do you know what I mean? And so, or that only appeals to like, a small fraction of humanity. I'm not saying books don't have enormous impact and haven't changed the world. And clearly, I believe that that's my true my own experience.

• 2:10:08Rich Roll?

  But it is such an ego trigger. Like, I wrote a book, and that book is in a bookstore. So I must be important.

• 2:10:14Ryan Holiday?

  Yeah, or that I want a seven figure advance or whatever. Or like, so I gave this talk to the to some people of the naval command last month in DC. And and I was talking about this too. I was like, if you're, but it's like, clearly, you didn't choose the Navy to get rich and to be famous. And yet, we make decisions. It's like, oh, but this command is more high profile. Or, you know, like, this one comes with a cooler car. And it's like, so you're, you made a very clear statement consciously or unconsciously about your intention and your priority when you chose this thing, you know. So why are, you know, you chose classical music?

• 2:10:59Ryan Holiday?

  Why are you mad that you don't have 20 million Instagram followers? You chose a niche. So like, be consistent about it. And your lack of consistency is is what's causing your spiritual angst.

• 2:11:16Rich Roll?

  Yeah, I mean, it goes back to the complexity of being human, right? We're still compelled by those base desires for power, money, status.

• 2:11:25Ryan Holiday?

  Well, and we're comparing ourselves to other people always, which is like, you know, the thief of joy, as Theodore Roosevelt said. Yeah, it's like, oh, okay. Like, I just have to remind myself of that. I'm not saying you can't make money writing books. But clearly, that's not what's the most important thing to me. Or I would be writing screenplays. Or I'd be writing advertising copy, you know, or, you know, I would not be writing at all because this is not. I'd be making, you know, I'd be a vlogger. There are so many other things you could do. It's like, I chose writing because actually I didn't choose writing. Writing chose me. That's what I do. That's, you know, and.

• 2:12:02Rich Roll?

  The other job that would be perfectly suited for you just doesn't exist in our era, which is the idea of the philosopher who is consultant of the leader.

• 2:12:11Ryan Holiday?

  Yes, sure.

• 2:12:12Rich Roll?

  How do we get back to that?

• 2:12:13Ryan Holiday?

  Yeah, I mean.

• 2:12:14Rich Roll?

  We could use a few of those.

• 2:12:15Ryan Holiday?

  Yes. Yeah, it would be, it would be relieving. It would be a relief to know there were some even conflicted hypocritical philosophers in Trump's court. But there are not. You know what I mean? It's the team of vipers instead. But yeah, I do, I do like that. I would, I would like that.

• 2:12:37Ryan Holiday?

  Especially because it's like, you know, maximum influence, minimum, minimal inconvenience and an utter lack of accountability. But I, yeah, look, it's like I write. I just remind myself, it's like I write these books because I think I have something to say and that and that. Look, I go, I write the books about the things that I write and I think they're important.

• 2:13:04Ryan Holiday?

  I'm, I'm not, Mark Manson is on a different path and a different calling. And I'm not denigrating his thing at all. I'm just saying like, we each have a lane. And, you know, look, some people are linebackers and some people are quarterbacks and some people are, you know, distance runners and some are sprinters. Like there's a biological component, there's a, you know, a training component, there's a personality component and you, you go like this is. The Stoics, you know, the, the Roman world was very strict in its hierarchy. So. You know, there's downsides to that, which is that, like they said, there's a slave hierarchy. But there was also this comfort in the idea of like, Marcus really didn't want to be emperor.

• 2:13:47Ryan Holiday?

  Not really, you know, he would have rather been a bookworm. But he's like, that's what happened.

• 2:13:52Rich Roll?

  Right.

• 2:13:52Ryan Holiday?

  And so I have to do my best to do the best at that.

• 2:13:57Rich Roll?

  But you as a writer, I mean, you're a living example of somebody who is in love with the process. Because you don't churn out books of your caliber year after year. I mean, you come out with a book every year. As soon as you finish, you're into the next one, the note cards are out and like you're like you're you.

• 2:14:16Ryan Holiday?

  It's a good.

• 2:14:16Rich Roll?

  There's nothing harder than writing. It's it's torturous and it's painful. And you have a practice and a diligence about it because you love doing it. Like you love the process of grappling with these ideas and trying to put together these thoughts in a cohesive narrative.

• 2:14:32Ryan Holiday?

  Yeah, and but so my output is either a sign that it's everything that things are very right or that things are very wrong. And I think it's both.

• 2:14:40Rich Roll?

  If a year goes by and you don't put a book out, then what does that say about who you are?

• 2:14:44Ryan Holiday?

  Yeah, why can't I enjoy it? Why do I have to like?

• 2:14:47Rich Roll?

  Yeah.

• 2:14:47Ryan Holiday?

  Writing a book also sucks.

• 2:14:48Rich Roll?

  What's your dad gonna say?

• 2:14:50Ryan Holiday?

  That's what I'm struggling with it, man. I'm trying to get to the bottom of it.

• 2:14:55Rich Roll?

  All right.

• 2:14:55Ryan Holiday?

  Yeah.

• 2:14:56Rich Roll?

  So let's let's leave everyone with a couple just key.

• 2:15:01Ryan Holiday?

  Okay.

• 2:15:02Rich Roll?

  Things about stillness, like if someone is listening to this, they're going to pick up the books, they're going to read it. But like, what are like, what are the core concepts that you want somebody to walk away with after reading this book?

• 2:15:13Ryan Holiday?

  Well, first, just this idea that stillness is really important, that stillness is where we feel happiness, where we feel contentment, where our best work comes from, where we make good decisions, where we're at peace. Do you know what I mean? That looks like we know when we've experienced stillness, it was wonderful. But why is it so rare? And how can we build habits and ideas and habits and practices and set priorities that make it less less of an accident and more of a intentional outcome? I'm not saying it's like, oh, this is good, like, you know, stillness is good for your work. So go get more stillness. But it's like, why are these wonderful moments so rare?

• 2:15:54Rich Roll?

  And it's not about going on a Vipassana meditation retreat, or pulling a geographic, or doing anything extreme. It's about building habits that create more of these moments in your daily life.

• 2:16:05Ryan Holiday?

  Yes, and, and having a set of people you admire who achieved it, that you look to.

• 2:16:12Ryan Holiday?

  And yes, some of the habits, I mean, yeah, it's setting a routine, it's being active, it's actively experiencing nature in some way. Oh, one of my favorite exercises from the Stoics is, and the most beautiful lines from the Stoics, it's not Marcus Aurelius describing the Colossus of Rhodes, or, you know, the aqueducts or the Colosseum. It's Marcus Aurelius writing about, you know, the way a stalk of grain is bending under its own weight, or, you know, the sound that plucking a grape makes, or, you know, he's talking about the furrowed brow of a lion.

• 2:16:53Ryan Holiday?

  And so he would have seen that in like some, the horrible carnage of the Colosseum. Do you know what I mean? But what he's, he's spotting, he's actively looking for beauty amidst what would have been a violent, disgusting, you know, dark place.

• 2:17:12Rich Roll?

  Right.

• 2:17:12Ryan Holiday?

  And so actively doing that, you know, it's not like, oh, look at that pretty sunset. It should be like, look at the lines on this table, like, how did, you know?

• 2:17:21Rich Roll?

  Yeah.

• 2:17:21Ryan Holiday?

  The, or finding it in the ordinary.

• 2:17:24Rich Roll?

  And that's being present.

• 2:17:25Ryan Holiday?

  Of course.

• 2:17:26Rich Roll?

  You know, I think of people that embody this quality as being like a lighthouse, right? Like, when somebody who exudes stillness, or is a living example of this, walks into a room, like, you know it, you feel it, and you're like, what is it about that person? Because they're standing in their strength and their power. And they're like, they're like a magnet that everyone is drawn to. And I think we're, we're kind of more prone to be chasing attention from other people, like, we're running after it, rather than gathering our strength and our resources so that we can stand in it and attract what we want into our life, rather than... Chasing it.

• 2:18:08Ryan Holiday?

  Well, that's why the the cover was really hard to crack on this book and it's a sun because I think it radiates out and I wanted it to be something masculine because I felt like it's like you can imagine. So you write this book and they give you all the template covers they want.

• 2:18:24Rich Roll?

  The font is gonna be like.

• 2:18:26Ryan Holiday?

  But it's like, you know, it's like some stones stacked on top of each other. It's a crystal. It's a, it's a, a, a stone dropping into some water, you know, or it's like a statue of Buddha. It's like, there's like 10 like sort of Zen images and they all tend to be pretty feminine. Not that there's a problem with that, but I do think it signals to people, to a large percent of the of the population that this is not for them. And in fact, it's like them who needs it most.

• 2:18:56Rich Roll?

  Right.

• 2:18:57Ryan Holiday?

  Um, and yeah, there's a Marcus quote. He's talking more about honesty, but he says like, you will know the honest and good person because they are like a smelly goat in the room. He's like, you, you know, when they're in the room with you. And I think that's true. Like even, even if, if you were in an airport and the Dalai Lama walked in in street clothes, I think you would know.

• 2:19:19Rich Roll?

  Mm hmm.

• 2:19:20Ryan Holiday?

  I think you'd know if you saw Jesus. I think you'd know if you saw, I think Socrates, Socrates was at your neighbor's house. You'd feel it.

• 2:19:27Rich Roll?

  And who would be a modern, current, living example of that?

• 2:19:31Ryan Holiday?

  I mean, this is a bad one.

• 2:19:32Rich Roll?

  Like in the world.

• 2:19:33Ryan Holiday?

  This is a bad one because it's political, but and I'm, I think I could say this, even if you despise every one of his policies, but I think Obama has that. I think he was, and he talks about this. He's like, I think it was because my mother was pregnant with me in Hawaii and she would just sort of sit on the beach and look at the ocean while he was in the womb.

• 2:19:52Rich Roll?

  Yeah.

• 2:19:53Ryan Holiday?

  There, he just had, he was unflappable. And you think about the shit that got thrown at him. It almost makes it more impressive. You know, even if you hate him, you're like, why did we never get to him?

• 2:20:04Rich Roll?

  Yeah.

• 2:20:04Ryan Holiday?

  You know, so I think he's a pretty great example.

• 2:20:06Rich Roll?

  Yeah, I would agree with that. I mean, I think, I think.

• 2:20:08Ryan Holiday?

  Thich Nhat Hanh is alive, so he, you know, he has it, the Dalai Lama has it, but.

• 2:20:13Rich Roll?

  Yeah, I'm thinking of people who are like in the culture, you know, like I think Sam Harris is a pretty good example of that as somebody who, who.

• 2:20:21Ryan Holiday?

  Although when he gets, when he gets like, he's gets into an argument.

• 2:20:24Rich Roll?

  Yeah, he'll, he, and he'll admit.

• 2:20:26Ryan Holiday?

  Yeah.

• 2:20:26Rich Roll?

  He'll admit when he falls prey to that. But in general, he's able to maintain a level of equanimity under duress.

• 2:20:33Ryan Holiday?

  I think so.

• 2:20:34Rich Roll?

  In a way that I think is, is interesting.

• 2:20:36Ryan Holiday?

  Yeah, I think so. Um, I think there's some athletes that, you know, have it in, in fleeting moments, we see it.

• 2:20:46Ryan Holiday?

  It's, uh, but it, it, it's one of those things where it's like, you know it when you see it.

• 2:20:51Rich Roll?

  Uh huh.

• 2:20:51Ryan Holiday?

  You know, we don't have.

• 2:20:52Rich Roll?

  It's an intangible thing.

• 2:20:53Ryan Holiday?

  Yeah, right. And maybe trying to describe.

• 2:20:55Rich Roll?

  And when you, and you're like, when you see it, you're like, I want, I want to be near that person.

• 2:21:00Ryan Holiday?

  Yeah. Yeah. Are you, you're walking along the ocean at night or you're walk out on the street? After the snow has fallen, you're the first one, you're just like, this, this is it, you know, but then. We're like the people in, watching the artist's present, then we're like, but that's my phone.

• 2:21:18Rich Roll?

  Yeah.

• 2:21:18Ryan Holiday?

  You know, or, um, oh, you know what? Like, let's go skiing tomorrow, you know, or I should take a photo of this, you know?

• 2:21:28Rich Roll?

  It's tough being human, man.

• 2:21:29Ryan Holiday?

  It is, it is tough. I, like, my wife, I, I remember, um, my wife said, you want to go in the pool? And I was like, yes. We went in the pool. And, uh, and I was like, you want to do laps? And she was like, we can just be in the pool.

• 2:21:45Ryan Holiday?

  But that's hard.

• 2:21:46Rich Roll?

  Right. That is, I think that's it in a nutshell, right?

• 2:21:49Ryan Holiday?

  Yeah.

• 2:21:49Rich Roll?

  Is it not? Yes. Cool. Well, uh, let's put a pin in it. All right, man. Until next time. Yeah. Um, I really, uh, do love this book. You did a great job. I think it's going to help a lot of people. It's quite an accomplishment.

• 2:22:05Rich Roll?

  I love all your books, but I really think that this is like taking it to a new and exciting place for a lot of people and I'm excited to see what happens with it. So Stillness is the Key comes out September 28th or something? October 1st. Oh, October 1st. Okay. Yeah. Excellent. And if people want to connect with Ryan, the best place to do that, RyanHoliday.net and your, sign up for your newsletter. You send out monthly reading recommendations. Yes, or just, uh, Daily Stoic. DailyStoic.com. DailyStoic.com. Yes. Right. Excellent. Yeah. And pick up the new book. Please. All right, man. Thanks for, uh, thanks for talking to me. Come back and do it again. I will. All right. Peace.

• 2:22:49Rich Roll?

  Wise Beyond His Years. He really is one of my favorite people. I really enjoyed that. I hope you guys got a lot out of that. For even more on Ryan, please check out the show notes on the episode page at richroll.com. And, uh, let him know directly how this one landed by sharing your thoughts with him on Twitter or on Instagram at Ryan Holiday. Also, don't forget to pick up a copy of his latest book, Stillness is the Key. I can't recommend it enough. If Ryan is brand new to you, please explore his entire canon of amazing books. And, uh, that should occupy you for the rest of the fall. Uh, if you're struggling with your diet, if you really are trying to master your plate once and for all, but feel like you lack skill in the kitchen, or the time, or the

• 2:23:31Rich Roll?

  budget, please check out our Plant Power Meal Planner. I know it can help you. We devised it, this digital platform with one goal in mind, to make healthy eating affordable, accessible, easy, delicious, nutritious. And I think we succeeded. I'm really proud of it. Basically, when you go to meals.richroll.com and sign up, you get access to Thousands of delicious and easy to prepare, plant-based recipes that are totally customized based on your personal preferences. You get unlimited grocery lists. You get grocery delivery integrated into the recipes you choose. So all the stuff just shows up at your house. That's available in most metropolitan areas. And you get access to a team of crack nutrition coaches at the ready to guide you.

• 2:24:13Rich Roll?

  And you get all of it for just $1.90 a week, which is amazing. Literally the price of a cup of coffee. So to learn more and to sign up, go to meals.richroll.com or click on Meal Planner on the top menu on my website. If you'd like to support the work we do here on the show, subscribe, rate and comment on the podcast on Apple Podcasts. That really helps us out a lot. So if you've dragged your heels and haven't done that yet, please take a moment to do that. It only takes a second. You can share the show on social media. Tell your friends about your favorite episodes. Subscribe to my YouTube channel, Spotify, Google Podcasts. And you can support us on Patreon at richroll.com/donate. Mad appreciation for everybody who helped put on the show today. I do not do this alone.

• 2:24:54Rich Roll?

  Jason Camiolo for audio engineering, production, show notes, interstitial music. Blake Curtis and Margot Lubin for videoing the podcast and putting it up on YouTube, including clips that we share there as well. If you haven't checked out the YouTube version of the show, I really strongly suggest that you do that. The production value is insane. Jessica Miranda for graphics. Ali Rogers for her beautiful portraits. DK, David Kahn for advertiser relationships and theme music by Anna Lema. Appreciate all of you. I love you. I will see you back here next week with psychiatrist, neuroscientist and author, Dr. Judd Brewer. He's coming by to discuss the neural mechanisms of mindfulness, which I think is a good bookend

• 2:25:38Rich Roll?

  to this conversation with Ryan. It's a really great conversation. You're not going to want to miss it. Here's a clip to take you out. And until then, be still. Peace. Plants. Namaste.

• 2:25:54Speaker 02

  You know, on a very basic level, we're probably all addicted to some degree or another. And classically, we used to think of addictions as these substances like alcohol and cocaine and heroin and whatnot. But really, I think that's a little narrower view. If we look at this, it can be virtually anything that gets us into trouble. You can have everyday addictions where it's cell phones and technology and trying to get our inbox to zero and all these things that are failing propositions. For the last 50 years, the dominant paradigm has been willpower. And that is proving to be more myth than muscle. It's more legend than reality. And that's exactly what I think we're seeing with meditation,

• 2:26:38Speaker 02

  is if we get out of our own way, our brains naturally work better. And we can really start to totally get in sync with life and almost get into the flow of things. That's one thing I like about mindfulness practices. It basically distills down to: Pay attention. See what the results of your behavior are. Repeat.