Ryan Holiday ON: Eliminating Fear From Your Life & Push Past Them This Year

Do you want to meditate daily with me? Go to go.calm.com/onpurpose to get 40% off a Calm Premium Membership. That's only $42 for the whole year! Experience the Daily Jay. Only on Calm Jay Shetty talks to Ryan Holiday about why being too comfortable won’t help you grow. When you take risks, you prepare yourself to be mentally and emotionally present and be ready for what may happen. Taking risks without fearing what might happen is the foundation that allows us to evolve for better even when constraints are present and some things are just out of our control. Ryan is a Wall Street Journal bestselling author, book store owner, public-relations strategist, and host of the podcast The Daily Stoic. Some of his best selling books are The Obstacle Is The Way, Ego Is the Enemy, Stillness is the Key, and The Daily Stoic. He owns and operates Painted Porch Bookshop, an independent bookstore in Bastrop, Texas. He lives on a 40-acre ranch in Bastrop County, Texas with his wife and two sons. What to Listen For: 00:00 Intro 04:42 It takes 10,000 hours to get to mastery 05:45 Opening a bookstore during the pandemic 10:27 How do you know which books to read? 17:36 What courage truly means 20:37 We’re all self-interested people but we value other people’s opinion 26:17 If you’re in a place where you identify with external results, you become vulnerable 30:34 Cultivating the ability to push through your fear 33:55 Being too comfortable makes you afraid to take risks 40:25 Deciding not to see the world as a zero sum place 45:00 When you make trade offs that aren’t worth it 46:07 Just how much is out of your control? 48:54 Positive changes out of situational constraints 51:17 What is heroism? 55:58 Ryan on Fast Five Episode Resources Ryan Holiday | Website Ryan Holiday | Twitter Ryan Holiday | Facebook Ryan Holiday | Instagram Ryan Holiday | Books See omnystudio.com/listener for privacy information. 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.

• 0:00Jay Shetty?

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• 1:28Jay Shetty?

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• 2:12Jay Shetty?

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• 2:18Ryan Holiday?

  And I think if you can get to a place where you're not identifying with the love or the mistreatment, you're just like, here's who I am. Here's the intention, the motivation that I know I'm acting on. And that I know that's coming from a good place. And so whether they're saying, Jay, you're amazing. Or they're saying, Jay, you're awful. You're screwing this up. You suck. You're just like, I'm going to do what I have to do as long as I'm able to do it.

• 2:54Jay Shetty?

  Hey, everyone. Welcome back to On Purpose, the number one health podcast in the world. Thanks to each and every single one of you that come back every week to listen, learn and grow. Now today's guest is someone that I've interviewed not once, not twice, not three times. But this is the fourth time we're sitting down together. The first time was at HuffPost back in like 2016, when I was just starting a lot of my online work. Then we did a Nasdaq Reads, probably around 2017, maybe 2018. And then I got to sit down with him on the podcast. You've already loved him on the show just last year. I think it was just before the pandemic. And then now we are having our fourth ever interview. I'm talking about the one and only Ryan Holiday.

• 3:39Jay Shetty?

  Ryan Holiday is one of the world's best selling living philosophers. His books like The Obstacle Is The Way, Ego Is The Enemy, The Daily Stoic, have all reached number one New York Times Bestseller status. And Stillness Is The Key appears in more than 40 languages. And all of his books have sold more than four million copies. Together, they've spent over 300 weeks, 300 weeks on the bestseller lists. He lives outside Austin with his wife and two boys and a small herd of cows and donkeys and goats. And he also opened up his own bookstore, which I love, The Painted Porch, and sits on the historic Main Street in Bastrop, Texas.

• 4:21Jay Shetty?

  And his new book, The Courage Is Calling, already a New York Times Bestseller. If you haven't read it, I highly Recommend that you go and grab it. Ryan, like you did for so many others, you opened up our minds and lives to the teachings of the Stoics, which I am eternally grateful for because I think you've brought so much wisdom through that we would have missed out on. And you also, in many ways, inspired me to think about how I could do something similar for Vedic philosophers and thoughts. So, thank you from a personal level, a collective level, societal level. For I've seen you do a lot of activism work too, but Ryan, welcome back to the show.

• 5:00Ryan Holiday?

  No, thanks for having me. And it's crazy. We do go way back. And I think both of us had somewhat circuitous journeys to where we are now. Like you interviewed me on two different shows before you had your own show. I did a bunch of stuff before I was a writer. To me, I, in case people don't pick up on what that means, is like, just because you're not like, very rarely does anyone just get to start like by having their own platform or putting out their own thing. And you have to take jobs or do things, you have to work your way there. And I think people who are in the middle of that, sometimes you don't know where it's going to end up. You can kind of lose faith. But I think in both of our cases, like we put in the work, paid our dues and we did get there.

• 5:45Ryan Holiday?

  And I hope that's encouraging to people because it's amazing. It always takes longer than you think it should, but eventually you get there.

• 5:53Jay Shetty?

  Absolutely. Yeah, I remember talking to you about like, you know, you started in marketing and you know, you talk about your time at American Apparel. And then I also remember talking to you about how you're the Leonardo DiCaprio of writers, where you'd written all these amazing books that were epic. And you were waiting for this, you know, the arbitrary idea of ranking on the list. And I, you know, I think we were talking about that last time when we were messaging. And I was like, you know, Leonardo DiCaprio has been nominated for an Oscar seven times and only won once. And that's pretty much the same as you. And, and it's just one of those amazing things that all your journey has brought you to this pace. And now when you look back. At your beautiful portfolio of books, and I know that Courage is Calling is the

• 6:37Jay Shetty?

  part of a new set of four books. I really like that you started with that point, that we've known each other through a lot of different faces, a lot of different names, a lot of different banners. And, you know, today, it's beautiful to sit with you and do this again. But, you know, it started very differently. But I have to be honest, I've had fun with you since day one. So I'm expecting this to be no different.

• 7:01Ryan Holiday?

  Well, you know, people talk about like 10,000 hours, right? That takes 10,000 hours to get to mastery. I think two things are easy to miss there. Number one, it's not 10,000 hours of terrible grinding labor. It should be fun. And I had a ton of fun along the way. And two, just because it might take 10,000 hours, or it could take 20,000 hours, or 100,000 hours to actually get to the place where you've really truly mastered it. That doesn't mean that you can't make a great living between now and then, and that you can't do work that you're proud of that stands up. Like, I'm, this is my, I think, 12th book.

• 7:36Jay Shetty?

  Wow.

• 7:37Ryan Holiday?

  I'm proud of all the books in between. But the 12th book is only possible because of the 11th, and the 10th, and the 9th, and the 8th. And the idea should be that you're on this journey, and that you're getting better as you go, even though you are, you know, not ideally where you want to be, but but you're you're having fun along the way, as you said.

• 7:57Jay Shetty?

  Absolutely. And I wanted to start off somewhere, before we dive into all the wisdom and the insight and the practices, I wanted to know, what does it feel like as an author during the pandemic to have opened your own bookstore called The Painted Porch? Like, that, it's, it seems like a really, it's like being an artist and then opening your own art gallery, right? And with other people's art in it, as well as yours, of course. Tell, what does that feel like?

• 8:20Ryan Holiday?

  Well, it was very exciting at first. Well, I think right around the time I saw you last, that was when I was thinking about doing it. And we'd sort of made some of the initial decisions to do it. And then, I believe we'd hired our first employee in February of 2020. So it was all very exciting. And then it got very terrifying, and very real, and very overwhelming quickly, because the whole world shut down. And

• 8:47Ryan Holiday?

  You know, I think we thought it would be a project that would take a year and it took two years. And that was obviously more expensive than intended and scarier than intended. But it also was an opportunity to take it slow, to do it right, to really think about why we were doing it and how we wanted to do it. And then it gave us a whole other sense of what the meaning of it was, right? So, you know, you're thinking, hey, bookstores are important because it's a place people go. You can be around other people. You can talk about things. And then when you, when we were looking at a world where that was not possible, you

• 9:28Ryan Holiday?

  suddenly realize what those things mean to you and you don't take them so much for granted anymore. So it was really, it was, it was a very trying and challenging experience, to be sure. But the upside was it made the rewards of it so far, you know, much more compelling and meaningful, I think.

• 9:47Jay Shetty?

  Yeah, I love that. It's wonderful. It's wonderful hearing that, you know, you've got through and you've figured it out and I'm sure it's been harder than it needed to be, but it sounds wonderful and I hope I get a visit. So I really look forward to actually going there. I've never been, never been able to go to a bookstore and say, my friend, my friend owns this and he's a writer. It's cool. So I really look forward to it.

• 10:08Ryan Holiday?

  No, I mean, books are such an amazing thing. Like if you think about what a book is, right? Like a book is 10 years or a lifetime of work and understanding bound between two covers for like $20. Like it's this incredible piece of technology that's, you know, now endured for thousands of years that I just, books have been so important in my life. Obviously, there's, there's different businesses I would open if what I was interested in is making more money. A bookstore in 2021, let alone during a pandemic is, you know, like not, not, not the best. But I think, you know, I have a podcast too, and there's something amazing about reaching millions of people at scale digitally throughout the world.

• 10:52Ryan Holiday?

  But but there is also something special about holding things and having a space. And so I just it it my wife and I were just thinking like, you know, we've been so blessed. We've got to do so many cool things. What is something that that could be fun, could also be a business opportunity? But, you know, I think improve the community in which we live. And that's kind of what I've just been thinking about more lately is like, not everything has to be like, how do I reach as many people as possible? It can also be like, how do you really reach the people, the smaller amount of people that you are reaching?

• 11:29Jay Shetty?

  Yeah, I couldn't agree with you more. For me as well, it's always been about scale and depth, scale and depth. And it's like, you know, you have scale, but how can you go deep with that scale? But then also, how can you scale down and take people even on a more meaningful and deeper journey more personally? And I was able to do that even digitally during the pandemic. We, a lot of me and my private coaching clients, people that I work with one on one, we started this like small meditation communities for them and their families or them and their friends on Zoom. And I was teaching, I'm used to teaching, you know, meditation on Instagram Live to, you know, hundreds of thousands or millions of people after people watch it on the replay. And to actually just sit on a Zoom with just 10 faces every single week.

• 12:11Ryan Holiday?

  Yes.

• 12:11Jay Shetty?

  Was beautiful. Like, it's been some of the most meaningful work I've ever done and you're you're spot on. So I get that. Now, I want to start, I've got so many questions to ask you, Ryan. So, and we've just been chatting. So I need to like, actually, everyone's gonna be like, what are you guys doing? Just having a conversation, which is partly what I'm doing. But I want to find out, you introduced Stoicism to the world in a huge way massively. Like, you know, really brought it out beyond where I think it had been, at least from my knowledge, at least for me, definitely. And and I wanted to understand, like, can you tell us the story of how you discovered Stoicism? And how that first moment made you feel?

• 12:54Jay Shetty?

  And why you felt compelled to share with the rest of the world?

• 12:57Ryan Holiday?

  I think a lot of what we're doing, you and I are doing, is sort of paying it forward, right? Somebody introduced you to the ideas and they hit you. And you had this amazing sort of life-changing transformation because of that. And then there's this kind of moment where you go, could I do that for someone else? And then we were talking about scale earlier. How could I do that like even better? How could I do that to, how could I take what I experienced? And not just do it to the people that I physically interact with, but millions of people. So I was in college and I went to this conference in West Hollywood. And the speaker was Dr. Drew from, from HLN and from Love Line. Now he has a wonderful podcast as well.

• 13:40Ryan Holiday?

  And he was speaking and I had grown up listening to Love Line. And so I, I remember at that age, I would, whenever I would meet smart people that I admired or that I had some, you know, random circumstances to me, I'd be like, what books do you recommend? Cause I was just, just thinking, there's so many books out in the world. How do you know which ones to read? And if you just, I was thinking, if I just read the ones that really smart people that I admire have read, I'll, I'll be like skipping all the, the stuff that, you know, it'd be like, it's like getting, you know, notes from, from, from people ahead of you. And so I asked him and he told me he was reading the writings of Epictetus, who is this Roman slave. And I, and I went back to my hotel room and I bought Epictetus and I bought Marcus Aurelius

• 14:25Ryan Holiday?

  because I'd seen the movie Gladiator. And, and, and these two books arrived and they, they hit me. I read Marcus Aurelius first, actually here, let me grab. This is my now 15 year old copy of Meditations. I've had to re-tape the cover on because I, I've read it so many times. But, but you know, you read Meditations and it just, it, it hit me, it hit me like a million bricks. I mean, in the, in the first line of Meditations, he says, and this is like one of my, he says, "When you awake in the morning, tell yourself the people I will deal with today will be meddling, ungrateful, arrogant, dishonest, jealous and surly." And he says, "They are like this because they can't tell good from evil."

• 15:10Ryan Holiday?

  And then, but he goes, "But they can't implicate me in ugliness, nor can I feel angry at my relative or hate him. We were born to work together like feet and hands and eyes. To feel anger at someone, to turn your back on him, these are obstructions." And I just, I just remember being hit by that going like, the emperor of Rome wrote this? Like he just wrote a note to himself about? How frustrating and annoying people are gonna be, but that he couldn't let this change him or make him angry. And that he had this obligation to work together with them. And, and I remember I was taking philosophy classes at the time, but it was nothing like this.

• 15:53Ryan Holiday?

  Like, when you read Aristotle, I mean, there's definitely good parts in it, but you're also like, what is he talking about? Right? Like, he's explaining the universe or something. He's not saying like, this is how you deal with a jerk in traffic. Or, you know, this is how you deal with your obnoxious roommate. Right? Like, I just love that Marcus Lewis was being so real and so practical, but at the same time, trying to be great, like trying to be decent and good and patient. And just that was transformative for me. And eventually, you know, got to a place where I thought, maybe I could write stuff like this, or I could write about stuff like this. And that's been the journey for me now for a decade and a half.

• 16:37Jay Shetty?

  Yeah, I love that. Thank you for sharing that so much. And, and I love so much about what you just said. So first of all, I want to point out to everyone who's listening, I love that you went up to someone and asked, what books do you recommend? Because that's such a great question, because 99% of people don't go up. And the 1% of people that do go up, they go up and say, how can I spend more time with you? Or how can I connect with you? Or how can, how can we have dinner or lunch? Or whatever it may be. And the answer 99% of the time is, I don't think I have time for that. Like, I'm not sure that's gonna happen. I'd love to, but it's, it's not possible. And so by asking them what books they're reading, you're tapping into their mindset for days, weeks, months, years, that you would never get time and access to someone that inspires you in that way.

• 17:22Jay Shetty?

  And thank you so much for reading the first one. I mean, anyone who listens to that, you're just like, I want to live like that, right? Like, that's, that's how you feel straight away. You go, I want to live like that.

• 17:33Jay Shetty?

  I want to share with you the biggest news of the year. How many of you want to meditate? I can see your heads nodding. I can see you raising your hands. I can see you saying, yes, Jay, I really want to learn to meditate. How many of you would like to learn to meditate with me every single day? Now, I already know what the answer is because I know how many messages, DMs, reviews, notes that I get saying, Jay, I'd love to meditate with you. Last year, we took meditation to Instagram and I meditated for around 40 days live and 20 million of you tuned in. Now, I am taking that same focus, that same presence to Calm.

• 18:16Jay Shetty?

  I've partnered up with Calm to release a new series called The Daily Jay, where you can meditate with me every single day for seven minutes to make it a real habit. I would love for you to come and join me and take part in building a really powerful meditation practice. And guess what? We're going to do it together. Head over right now to calm.com/j to get 40% off a premium membership. That's calm.com/j.

• 18:49Ryan Holiday?

  Well, the crazy thing about the book question is, so like even today, you know, I got a bunch of emails from random people, which is all very nice. I'm not going to be able to respond to all of them. But somebody was like, hey, I'm struggling with depression. What's a book you would recommend? And I would like, it took me two seconds to reply, right? And like of all the emails today, that's the one that I responded to because I love books and if that's an easy way I can help a person. But the crazy thing about the Dr. Drew story was like three months later, I went to a different conference and he was there again. I don't know how, I don't know how the, the odds of it work. But I went up to him and I was like, you probably don't remember me, but I read those books, right?

• 19:32Ryan Holiday?

  And he was like, I do remember you, but I did not think you were going to read those books. And he and I are friends now, like 20 years later, 15 years later, we, we still know each other because I didn't just get the recommendation, but then I actually did the work, like I read the book and now he and I have this connection forever. And I think. The amount of people that like asked me for recommendation versus the amount of people I hear back from who have actually taken the time to read the book, you know, it's it's a small percentage of a small percentage. And so these books are out there, these books that have changed people's lives, people have been through the exact same thing that you've been through, they're there, but no one can read them for you.

• 20:16Jay Shetty?

  Yeah, no, absolutely. Well said. And this leads us nicely to Courage is Calling, the, you know, the new book, because to me, you know, we have this perception that to have a great life, we need to be brave, we need to be courageous. But you actually start the book at fear. And, and I think what's fascinating about that is a lot of people have the fear, or we think we lack the courage to go up to someone and ask a question. Then we fear taking the step of ordering the books because we're thinking, oh, well, when will I get time to read them? And they're just going to become a doorstopper and then maybe I'll feel worse about myself. Or maybe we get beyond that and we order them. And then

• 21:00Jay Shetty?

  we fear reading them. We go, oh, no, well, that may need me to change, or that may need me to shift, or I may have to give up some luxury or some comfort that I'm used to. There's fear at every single step. Walk us through how fear can be something that is necessary, but is also just expected.

• 21:18Ryan Holiday?

  Well, you make an important point about courage, which I really tried to build the book around, which is that courage is not just running into battle, or a burning building, or jumping out of an airplane, or, you know, it's not just physical danger. And it's not always dramatic, right? So there's physical courage and moral courage. Moral courage is also the courage of a whistleblower, or a truth teller, or a transgressive artist. But it's also just the courage to like walk up and talk to a stranger, or the courage to, to start your own podcast, or the courage to put yourself out there, or to, you have this, like, I don't know, the decision to cut your hair a certain way and not give a shit what anyone thinks, right?

• 22:02Ryan Holiday?

  There's also this really small day-to-day courage. It doesn't, it's not always this dramatic glorious thing. And I think you're right, like a lot of, a lot of really basic things in our life come down to a failure of courage. Even, even you think about people who are afraid to try something, not because they're afraid of failing, which they probably are, but also just afraid of, of, of success, right? Like afraid of what, what changes would be demanded or what it would mean to then have to wrestle with this thing. And so it's, it's not that we don't know what we should do. It's that we have a million reasons why we shouldn't do it. Right, right? That's what fear is.

• 22:47Ryan Holiday?

  Fear is the thing that gets in the way, uh, what Steven Pressfield calls the resistance between, you know, what we can be and where we are. So it's not that courageous people do not feel those fears. It's that they push past them, right? The things we want in life are on the other side of that fear. Like all good things in life require courage. I would imagine there's very little that anyone listening could think of in their own life that they're proud of, that did not require some triumph over fear. Certainly everything that I'm proud of in my life was something that I had to push myself out of my comfort zone to get.

• 23:30Jay Shetty?

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• 24:13Jay Shetty?

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• 25:38Jay Shetty?

  Terms and conditions apply. See webpage in studio for details. Yeah, absolutely. No, I think you're spot on. I mean, yeah, when I'm thinking about that right now and I hope everyone who's listening or watching is thinking about that too. I can't think of, I can barely think of anything, if anything at all. And so, you know, that aligns very strongly. And I like, you know, in the book, there's the part that you wrote that says, "And there has never, ever been a time when the average opinion of faceless, unaccountable strangers should be valued over our own judgment." And, and I love that because I think we're living at a time when faceless, unaccountable strangers dictate everything in our lives, whether it's a comment, whether it's a DM, whether it's a,

• 26:24Jay Shetty?

  you know, a message, an email. Walk us through, why is it that we take?

• 26:31Jay Shetty?

  Unaccountable facing strangers so seriously, why does that exist?

• 26:34Ryan Holiday?

  Look, it's not like this just some modern thing, right? In Meditations, Marcus Aurelius says, "The crazy thing is, we all love ourselves more than other people. We're all self-interested selfish people, to a certain degree, right? And he says, "And yet, we value other people's opinions more than our own." Right? You see this sweatshirt you like, and you buy it, and then someone's like, "What's that?" You're like, "Oh, you don't like it? I shouldn't like..." You know, like, or you spend, on the other end of the spectrum, you know, you spend two years writing a book, and then you go, "But, but did the critics accept me? Did the publisher like it?" You know, you can even find yourself, "Is it any good?" And it's like, who is this person to decide that it's any good? You're the one, you know, this is why you do what you do.

• 27:18Ryan Holiday?

  And yet, we hand over approval, success, to other people. And like, look, when, when The Obstacle is the Way came out, just to, just to sort of illustrate this idea that nobody knows anything. The publisher offered me half what they'd offered me for my first book, for what was my second book. So, right out of the gate, I had the idea for The Obstacle is the Way, and the publisher said, "That idea is half as good as your last idea." They, they like, they did not believe in it. Look, they believed in it enough to, to purchase it, but they, they did not have high hopes. A close friend of mine, I found out later, predicted that it would sell 5,000 copies, right? It came out, it didn't hit the bestseller list the week it came out.

• 28:03Ryan Holiday?

  It sold like maybe 30,000 copies in the first six months, maybe 60,000 in the first year. Did not hit a bestseller list for the first five years of its existence. And then ultimately, it's gone on to sell, you know, about a million and a half copies. So, the success of that book, if I was judging it based on what other people said, would have been a failure, would have been a disappointment, would have been mediocre at best. But what I knew is that it was, one, something was really important to me. Two, I knew it was something that, because it had been so important to me, that with time, it would resonate with people.

• 28:46Ryan Holiday?

  And then, three, it was pleasurable and exciting and rewarding for me to do. And so, kind of, everything beyond that was extra.

• 28:57Ryan Holiday?

  I moved on to other projects and let it do what it did. So the fact that it's now had all this success is one is a wonderful bonus on top. But that that wasn't why I did it. Because if it was why I if that was what had been motivating me from the beginning, I never would have done it because it would have been killed the second the offer came back from the publisher and they said eh, you know, and that that is how it works in life. There, you know, people are often worried about somebody stealing your idea. And there's a great line from a physicist, whose name I'm forgetting, but he said, don't worry about that. He says, if it's an original idea, you're gonna have to ram it down people's throats because people aren't gonna get it at first.

• 29:38Ryan Holiday?

  Everything that's new, exciting, innovative, important was unappreciated or outright despised when it came out. So you have to be able to cultivate this sense of why you're doing what you're doing, why it's valuable, why it's important, what it means to you. And you have to get to a place where you're a little bit indifferent, which is a stoic term, meaning that if people love it, great. If they hate it, that's okay, too. But you have your own sense of it. And that's what what allows you to sort of ignore both of those things.

• 30:13Jay Shetty?

  Yeah, no, that that indifference I find so fascinating because when you first hear it, it sounds like there's no fun and and it sounds like there's no joy. But actually, when you live it, it's liberating. And and I find that there's something really fascinating. I remember first coming across that when I was around probably like 20 years old. I was the the president of a youth organization back in London. And I took on this role at about 18 years old. I was given it. I didn't audition for it. I didn't apply for it. I was given it. And for two years, my life was hell because everything I did was massively criticized because it wasn't as good as the previous president.

• 30:55Jay Shetty?

  And so and I was a I didn't knew nothing about leadership. I mean, you know, leadership is a really big, complex, conscious, thoughtful thing. I was 18, didn't know anything. Anyway, for two years. Everything I did was criticized, it was ridiculed, it was compared. And I started to feel really bad about myself. But the one thing I held on to was that everyone's criticizing me for my management, but not for who I am. And, and I held on to that very closely. I was like, okay, I'm a bad manager, I'm a bad leader, I'll take that all day. No one's saying I'm a bad person, I'm gonna hold on to that. And then something really fascinating happened that we had a fundraiser when I was about 20 years old. And that fundraiser I like outperformed, where I've raised lots of money for this really important foundation and all this.

• 31:40Jay Shetty?

  And all of a sudden, the same people were like, oh my God, Jay, you're like the best thing in the world and you're incredible. And it was that day that I promised myself that I would remain indifferent. And I promised myself, I remember still now at 21, promising myself going, I am not going to let the opinions of other people make me feel good or bad. And that doesn't stop me from feeling joy because I get to feel good for myself when I feel like I've done something, right? Does that, does that feel right?

• 32:06Ryan Holiday?

  Yeah, totally. It, it's kind of similar to in, in meditation, right? You have these thoughts and you realize you don't have to identify with the thoughts. They can just exist, right? Like a cloud exists and it's there in, in your view. And then it drifts off and you don't really know what happens to it, right? And I think this is where we want to get with success as well as criticism or failure or, or worse, right? Like being attacked undeservedly. Mark Schubert talks about being able to accept success without arrogance and let the rest go with indifference. And I think if you can get to a place where you're not identifying with the love or the, the, the mistreatment, you're just like, here's who I am.

• 32:50Ryan Holiday?

  Here's the intention, the motivation that I know I'm acting on. And that I know that's coming from a good place. And so whether they're saying, Jay, you're amazing, or they're saying, Jay, you're the, you know, you're awful, you're screwing this up, you suck. You're just like, I'm gonna do what I have to do as long as I'm able to do it. And I'm not gonna identify either way. And I think, you know, people sort of nod their head along with this. It's easy to identify with the success on the way up. But then what happens to those people is what happens when you inevitably screw up, run into bad luck or whatever. You think about an athlete. If an athlete is identifying with

• 33:32Ryan Holiday?

  the hot streak that they're on, well statistically, that's just not going to last, right? And so you have to become, you have to understand that you're going to lose, that you're going to miss, you're going to screw up. And if you're in a place where you identify with those external results, you're really, really vulnerable and you're going to be really unhappy, especially in those dark, those dark, dark moments.

• 33:59Jay Shetty?

  Yeah. So Ryan, then what do we do with fear? If everyone's listening or watching, they're going through the fears that we know that they are. What do we do with fear? I feel like it's such a, we're almost scared of the emotion in and of itself and then we panic.

• 34:12Ryan Holiday?

  Well, the Stoics obviously believe in the power of reason, right? And a lot of fear, you could say is unreasonable, right? Like you think about failure, right? Let's say you're putting out a book, I'm putting out a book and you're like, what if it doesn't do well, right? And you're sort of scared of this. What the Stoics would say is, what if that happens? Like, what does it actually mean, right? Not like, oh, it's this vague unpleasant thing, but what does that look like? Well, you already got paid for it. You already did the thing, right? Like actually it failing is nothing. It doesn't matter at all, right? Like it's not what you would choose, but you're not going to end up under a bridge. They're

• 34:56Ryan Holiday?

  not going to tar and feather you or something, right? Like there's, there's no consequences. And so this is a really important thing. I remember when I was dropping out of college, I was so scared about it and I was so convinced that I shouldn't do it because I was afraid of what might happen. And I remember one of my mentors goes, you know, he says like, when I, when I was in college, I got sick for a year and I spent, he spent a year in the hospital. And I was like, and what happened? And he was like, it's literally not come up once in my life. He's like, I graduated in five years instead of four years. He's like, the worst thing that could happen here is that you just go back to school and you have to make up for the time that you missed. And, and that was really important, right?

• 35:41Ryan Holiday?

  Like the, to break down the thing that you're afraid of, to really think about the worst case scenario, right? People are afraid of, of, of like, uh, that I have stage fright, right? I don't like talking in front of crowds. Literally, what is the worst thing that could happen? A bunch of strangers you'll never meet again, don't like you? Like, you'll be totally fine. And so part of what we should do with fear is really break it down. Because sometimes, hey, I'm peering over this cliff that, uh, someone's telling me to jump off of, um, maybe that's a really bad idea, right? Sometimes you use the power of reason and it reminds you, oh, this is a bad idea. I, I can't afford to lose this. But most of the time, we break those fears down and then we're better able to manage

• 36:24Ryan Holiday?

  that fear because we have a rational understanding of it, instead of this sort of irrational, emotional understanding of it.

• 36:32Jay Shetty?

  Yeah, and it's incredible, once you break through that fear, how now you're looking at it and you're like, I can't believe I was ever scared of that, right? Isn't, isn't that just such a fascinating trick of the mind? That as soon as you break something that felt insurmountable, now when you've overcome it, you, you're almost laughing at yourself. Like, how, how was that the thing that helped me back?

• 36:53Ryan Holiday?

  Well, so each time you do something that you were afraid of, you push through, you have more confidence, right? You have a, like, dropping out of college made it easier for me to then leave my corporate life later to become a writer, right? Because it was like, oh, I could just go get another job or I could get the same job again, right? And so you, you not only get a certain amount of confidence from it, but you also Get a better understanding of how things work. The problem is when you give into fear, not only do you not do the thing, now you actually have less information about how the world works. And so, you know, there's that, that sort of cliche about do one thing every day that scares you. It's actually pretty good advice, right? You're sort of building the muscle.

• 37:36Ryan Holiday?

  You're building that ability to override the, this seems scary, but I'm going to do it anyway. I think cultivating that, that ability to sort of push through that fear is really important. And, and I think, again, these sometimes can be very pedestrian fears. It's like, I remember the decision for Daily Stoic, which is one of the, the things I do, the decision to like make videos, right? Like, and I remember talking to you about this. It's like, I was very comfortable writing things. I was very comfortable being on stage. But the idea of making a video, like, I was just scared it would be bad. I would, I think I was really scared of being uncomfortable in a new thing.

• 38:20Ryan Holiday?

  And, uh, but pushing past that, it's opened up this sort of whole avenue for us. But then also, you know, the decision to make sort of long form videos also made it easier to be like, oh, TikTok's this thing. Now I can, uh, you know, you, what you're cultivating is the ability to be comfortable being uncomfortable.

• 38:41Jay Shetty?

  Yeah.

• 38:41Ryan Holiday?

  And knowing that you'll figure it out and eventually get comfortable again.

• 38:46Jay Shetty?

  Yeah. And what I find so fascinating about what you just said, Ryan, is that even when we make big leaps or we break through or we find courage, it's so easy to get comfortable again. Like, it's fascinating, isn't it? Like, I, I remember when, so when I went off to become a monk, obviously I broke that barrier completely. I was like, I don't care if I get a job, it doesn't matter. So I felt extremely confident and courageous. Not that I use those words, but that's what I would have felt at the time. And then when I left being a monk, it was a tough time, but again, that was a tough decision. So that built more courage and confidence. Then I found a job, but as soon as I got into a job, I remember leaving that job. I mean, I left it within two years, but it's like,

• 39:26Jay Shetty?

  There was a moment that that comfort started to feel really safe and comfort is like really alluring. It's it's really mesmerizing and I find that comfort really convinces you that this is it. Settle for this. It's safer. It's better. It's happier. What are the things that you do to build that courage muscle every day or do something out of your comfort zone? So that you don't get comfortable. Is there something that you've been working on or or something that you've seen others do that you've spoken to on your podcast?

• 39:56Ryan Holiday?

  Well, this is the paradox, right? We tell ourselves like, I can't do it now. I'm gonna wait till I'm more financially successful. I'm gonna wait till I'm more well known. I'm gonna wait till I put in more years or then I'll speak up. Then I'll put myself out there. Then I'll take this risk. It'd be wonderful if it worked that way, but in fact, it's the exact opposite, right? You think, oh, after I've put 10 years into this company, then I'll put out this new idea, then I'll stay. But no, now you don't want to lose 10 years of work, right? You'd think that the financially successful people would be the most comfortable taking the risks. But they have the the luxury, the privilege of knowing exactly what it might cost them, right? And they know how hard they had to work to get there.

• 40:41Ryan Holiday?

  And so this is why people are afraid to be politically active. This is why people are afraid to voice unpopular opinions. I'm sure you and I both know people with platforms that have really strong opinions about things that are happening in the world. They just don't want to get involved because they know how hard it was to get where they are and they don't want to lose that. And so you do have to cultivate again to go to this kind of indifference. Like, look, it's wonderful to have the audience. It's wonderful to have the fancy stuff. But you didn't like, I I say this to people who sometimes get mad about things I say. They're like, how could you say that? Didn't you understand you would, you know, make me angry or whatever? And I go, look, I didn't cultivate this platform to not say what I think, right?

• 41:23Ryan Holiday?

  Like, the job is not having the platform. The job is not this or that. The job is doing the thing, right? Is the the speaking the truth, saying what needs to be said, speaking to what I think is important. And so. We can really lie to ourselves. We can tell ourselves, later, I'm gonna do this. Right? We say, oh, I need to make some money first, and then I'm going to, you know, write that screenplay, or do that thing, or whatever. You're not gonna do it, because then you're gonna be too comfortable. And so, you, you, you kind of have to see that comfort, that, that like, taking it for grantedness, as the enemy, because it's, it's what makes you afraid. You don't wanna lose it.

• 42:07Jay Shetty?

  Yeah, I, I'm so glad you said that. And I went through something similar recently with, with some of my team, where I was explaining to them, they were saying, Jay, don't you think that's a risk? And I was just like, well, I work this hard so that I can take more risks. Like, I had to take risks to get here, and I'm only excited if I'm able to take more risks and try new things out, because what was the point otherwise? I'm already living in bonus land, right? Like, I'm already-

• 42:32Ryan Holiday?

  You're playing with house money.

• 42:33Jay Shetty?

  Yeah, yeah, exactly. You're living in a space that you're just, I'm so much more blessed than I ever thought I would be. And so, with that, I feel comes a bit more responsibility, comes a bit more desire for risk. And I'm not just talking about risk for personal growth. I mean, I mean, to try things that I think are beneficial, or to help others, to serve, or do things that may be unexpected of me, because I understand how that leads to more impact or service.

• 42:57Ryan Holiday?

  Yeah, there's a great story about Lyndon Johnson, when he proposes passing the civil rights legislation. And one of his aides says, you know, maybe you should wait till after reelection. They said, this could be bad. You know, it's gonna be risky politically. And he says, what the hell is the presidency for? Right? And it's important to realize that literally the most powerful man in the world was struggling with, and, and this is, that's how seductive it is. You, you get all the way to the top of whatever it is that you're doing, and then there's reasons, right, that you shouldn't do X, Y, or Z. And at a certain point, you have to say to yourself, what was the point of all of this, if I'm not gonna do what I care about, what I like, what I love, what I think

• 43:40Ryan Holiday?

  needs to be done? And that's really what courage is about, the courage to say- I'm not going to think about those consequences. I'm going to do it because it is the right thing to do come whatever may. And there's no question that things I've written, things I've said, things I've done have cost me a certain number of followers, let's say, which ultimately can translate financially. But I'm proud of what I said. I'm proud of what I put out. I can look myself in the mirror. And one of the questions I ask myself, and I'd be curious if you think about this too. As someone who didn't create the things that I write about, like Stoicism is this way of thinking that's existed now for 2,500 or so years.

• 44:24Ryan Holiday?

  And I happen to be a well-known sort of representative of that idea, but it's not mine. And so the thing I tell myself is, or the test I have is, am I being a good steward of that philosophy? Yes. And so if I'm afraid to, it would be the same thing for the presidency. You're not, you don't own the presidency. You're just the guy or woman sitting in that chair right now. And the question is, are you being a good steward of the office, of the occupation, of the opportunity? Or are you just protecting what's good for you in the moment? And so I think about, you know, is this the right thing to do or talk about?

• 45:08Ryan Holiday?

  Not, is this going to win me the most friends?

• 45:11Jay Shetty?

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• 45:46Jay Shetty?

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• 47:14Jay Shetty?

  Head to wayfair.com to shop all things home. That's W A Y F A I R dot com. Wayfair, every style, every home. Yes, yeah, absolutely. Yeah, no, and I think I asked a very similar question. Like, for me, it's, you know, it is servatorship, it is figuring out, like, to what degree? And a big part of that for me has always been, if I see other people helping the world, how do I view them?

• 47:43Jay Shetty?

  And it was really interesting. I was sitting with my team recently and like there, you know, I think I've always been a fan of yours and you've known that from day one. But you know, it's like for me, when I see other people who I believed are positively impacting people's minds, I want to collaborate, connect, do more together because I, I feel like we need more of that. And I was speaking to my team recently because I was, I was talking about collaborating with someone and they were saying, well, Jay, you know, like, maybe they're, you know, like, maybe they see as competition. And I was just like, well, why would I compete with someone who's trying, who has the same goal as me, it seems. And I think that's how I try and measure where my intention is because often, you know, if I get lost in that hierarchy myself, that's when you start to recognize that your intention isn't as pure as you think it is.

• 48:26Ryan Holiday?

  Well, this is another thing I think requires a certain amount of courage as far as one's worldview. What you're talking about is deciding not to see the world as a zero sum place, right? So some people go through the world and they're like, this is about my career. This is about my success. This is about my family, right? This is about my business. And, and there's no question that attitude, because it's so singularly focused, can make you very successful. But I think it's more enjoyable, ultimately morally rooted to, to go through the world and thinking about it as, how does everyone win? How does everyone get something out of this? And that was something, you know, I started my first email list, not talking about my own work, but just recommending

• 49:06Ryan Holiday?

  books that I've loved. And I've done that now for, since, I don't know, 12, 13 years. Like, I hear just as often from people who, their lives were changed not by something I wrote, but by a book from someone else that I recommended. And, and, and that was a big breakthrough for me realizing, oh, not only is it not zero sum, but that helping other people, just being a resource, period, also helps you. And so I think, you know, with your podcast, like, look, you could just make your own content every day, but the decision to talk to and share other people's stuff, it benefits you and them. And I think the more, the more secure one can be

• 49:51Ryan Holiday?

  in themselves, the more helpful they can be to other people. And then ultimately, the more impact everyone can have together.

• 49:59Jay Shetty?

  Yeah, absolutely. I love that because I was sharing with someone recently, I was like, you know, one of the, and I feel this is what you've done with the Stoics and what you were sharing for Marcus Aurelius. But you know, for me, I've just always been fascinated by studying people's lives. Always been fascinated by studying and I love studying people and mindsets and decisions and choices. And, and I was thinking that we all have to look at people and we all have two choices. You either study people or you envy people. Those are the only practically two choices you have. If you don't deeply study, there will be some comparison, some envy, some criticism, some, some sort of unhealthy trait that comes out. And if you study someone, then you appreciate, you admire, you honor.

• 50:43Jay Shetty?

  And I know that in my life, I would rather live with admiration, honor, appreciation of others than the other stuff. And so I naturally gravitate towards how can I study someone's life? And when I see you studying the Stoics, that's what you're doing. You're studying their life, sharing your study and your notes with us. And, and to me, it's almost like thinking, oh, you know, that person just sold their house on our street for X amount of money. Oh my gosh, that house is not worth that much. It doesn't look that good. You're not realizing that the whole value of the street just went up because of that house. And, and I think that's where people don't recognize that, that collective good is always better than individual success.

• 51:22Ryan Holiday?

  Yeah, there's a great joke I heard that, that envy is the only sin that isn't any fun.

• 51:27Jay Shetty?

  Ah, yes.

• 51:27Ryan Holiday?

  Right? Like, sex is fun, even overeating is fun, right? All, most of the deadly sins are at least fun while you're doing them.

• 51:35Jay Shetty?

  Yeah.

• 51:35Ryan Holiday?

  Envy sucks. No one is having less fun than the person who is being eaten up with envy and jealousy.

• 51:43Jay Shetty?

  Yeah.

• 51:43Ryan Holiday?

  And so the, the decision, and it does have to be a decision because I think there's probably some evolutionary reasons why we feel envy.

• 51:52Ryan Holiday?

  The decision to say like, I'm just gonna be happy for people. I'm gonna help other people. I'm gonna help other people and not ask for anything in return. I'm just gonna try to put good stuff out in the world. I'm gonna try to use my assets to help other people. And I hope other people do the same, but I'm not gonna be pissed off when that doesn't happen. That's a real lifestyle choice. And I've tried both and the other one is just, it's not fun. And it doesn't get you what you want, you know, being, being bitter, being resentful, being... Closed off or selfish, it's not fun.

• 52:30Jay Shetty?

  Totally. And if, and according to your line of thought, which I like, is that if there's an evolutionary purpose of envy, one of them potentially could be to lead us to study, right? To study what we envy, like that's something that could, I have no idea, that's not a factual thought, it's just an idea that I'm having that. Yeah, like envy would make you go, oh, well, let me deeply look at that. Let me understand how that person got there. Let me, let me actually lead to study through that, right? So it can be healthy and useful.

• 53:01Ryan Holiday?

  Let's look at the trade offs, right? I think oftentimes too, the thing, the person that you're jealous of, if you had to go, but is it actually fun to be them, right? Like, I think oftentimes we'll look at something that someone has and will want that thing, so we'll be jealous of them. But we don't understand that it's impossible to separate that thing from all the other parts of them. And so it may well be that it's a bad bargain, right? And that the reason you don't have it is that you understand that those other trade offs they made aren't worth it, or perhaps they're impossible for you. And so I think just really understanding like what you want, what you have, that's another big part of it. The Stoics talk about like how jealous you would be of yourself

• 53:45Ryan Holiday?

  if you didn't have those things, right? Or how sad you would be if they went away. And so instead of being jealous of other people, just step back and try to practice some gratitude for what you have. These are all ways, I think, of getting to a happier place.

• 54:01Jay Shetty?

  Yeah, for sure. I wonder from you, what is something currently that, there are two questions here. I'm gonna ask both of them now and then you can take them. What is the thing that you've been in the last 12 months fearing the most? What has been a fear that you've been tackling with? And then second question to follow that up with is, you know, what do you think is personally the most courageous thing that you've done recently? And it doesn't have to be huge, right? Like, that's the point.

• 54:26Ryan Holiday?

  I think I have easier time answering the first one than the second one. But I have two young kids. And so when you go through something like this pandemic, what you're really forced to grapple with, and this is a big Stoic concept, is like just how much is out of your control, right? Like, you care about these people, this thing, more than anything in the world.

• 54:49Ryan Holiday?

  Yet you don't control it, right? You it's they're running around, they're outside. And so I think one of the things I've really had to grapple with over the last 18 months is anxiety, worry, right? A certain amount of powerlessness, a certain amount of frustration with just that we're in this mess as a society or as a planet. And and and so I think, you know, when we talk about parenting, I don't think we talk about courage enough, right? So first off, just to be a woman who brings a child into the world is an insanely courageous thing to do. If you just think about like, I mean, look, women die in childbirth all the time and yet women get pregnant all the time.

• 55:32Ryan Holiday?

  Like, I think we we've gotten so used to it, or perhaps we just don't think about what insanely courageous act it is. But then to be a parent in this sort of crazy messed up world, I think about all the parents that I know, I just try to think about all the parents in the world that have had to endure this, you know, insane disruptive life event that has challenged us in so many different ways. It's been, you know, it's been it's been a journey. And I think when we think about what Stoicism is, or we think about what Buddhism is, or any of these philosophical schools, they were designed precisely for these kinds of events.

• 56:15Ryan Holiday?

  Like, the ancient world was, you know, people talk about things going back to normal. This is normal. This is what life was in the ancient world. This is what life was like in our grandparents' lives. And we're just, we were just really, really spoiled for a long time. And now we're having to wrestle with, hey, the world doesn't really care about you or your plans, and you're gonna have to figure out how to accommodate yourself to those things and manage to be happy and productive and, you know, not a wreck inside of them.

• 56:46Jay Shetty?

  Yeah. And do you do you genuinely believe, and of, you know, pandemic aside, of course, because That it's a huge, huge, huge thing that obviously affected everyone on the planet. But do you generally believe that a disruption of plans has led to better plans, results, ideas, innovation, inventions?

• 57:04Ryan Holiday?

  Look, no one would say like, hey, in America, you know, 750,000 people have died, that this is a blessing in disguise, right? That would be offensive. But we add on top of the tragedy by refusing to change or be changed by what's happened. Right? So I don't know about you, but this was an enormous forced lifestyle experiment. We had to reimagine a lot of things. We probably wouldn't be doing this remotely, you know, if it weren't for the pandemic. You know, there's things that you're talking about those meditation groups that you made. There's things you've created as a result of the constraints of what was happening in the world that are on net positives for you.

• 57:48Ryan Holiday?

  And that's certainly been the case for me. It's forced me to reimagine, rework a lot of what I sort of took for granted previously. I think coming out of the pandemic, I'm not going to travel nearly as much, not for safety reasons, but just realizing, oh, I've been going a mile, you know, a mile a minute for 30 odd years of my life. And I was aware of what I was getting out of it, but I was less aware of what it was costing me or what it was preventing me from doing. And so I think that it's not that the Stoics would say that everything terrible has something

• 58:29Ryan Holiday?

  wonderful inside of it, but that by wrestling with what's happened, by looking for what we can do inside of what's happened, we manage to excavate little bits of positivity or opportunity for progress. And that's what the obstacle is the way is really about.

• 58:47Jay Shetty?

  Yeah, beautiful. And so we've talked about Fear, we talked about courage. The third part of the book is the heroic. And I find this, and I love that it's obviously towards the end, but it's, I found this fascinating because I think everything in society makes us want to be a hero. Like the movies I watched made me want to be like the guy in the movies. The adverts make me want to be like the guy for me or, you know, for people, the girl or that person in the ad, in the movie, in the book, in the story. But, but you know, you define what it means to be a hero morally and physically. I want you to break that down for us. Like, how do you introduce this and how did the Stoics think about this?

• 59:27Ryan Holiday?

  So if we think of courage as the triumph over fear, maybe what we're saying is that heroic is something beyond even that. So in the book, I'm talking about Michael Jordan's decision to leave basketball to play baseball. That's an immensely courageous thing because it's risky. People are critical of it. He has no idea if he can go from being the best in the world at one sport to starting at the bottom of another sport. Now, that was a courageous thing to do. But I contrast that with Maya Moore's decision, equally dominant in the WNBA, to walk away from basketball to free a man wrongly convicted in prison. Right? So she's not just doing something courageous. She's doing something heroic because the primary beneficiary of what's happened is not her.

• 1:00:12Ryan Holiday?

  Right? So heroism to me, or the heroic, is when we do something courageous that's well beyond our self-interest or perhaps very much at odds with our self-interest. Right? When we talk about the courage to start a business, you know, what we're talking about is pushing past doubts or risk or whatever. But what about the courage to leave a successful business to start a nonprofit? Right? You're, you're, you're not putting yourself in physical danger, but you're putting your interests behind the interests of other people. And that's a very scary, difficult thing to do.

• 1:00:53Ryan Holiday?

  And it's heroic because by, by putting others above us, we're actually elevating all of us. And so I wanted to look at that because I'm really, really, really inspired by that. And that ultimately is what I think we need more of in the world. Obviously, we need courageous entrepreneurs, but we need people who are willing to do something beyond just trying to make something for themselves.

• 1:01:17Jay Shetty?

  Yeah, I deeply appreciate that definition. Thank you for sharing with us because to me, that that journey from courage to being heroic, that is that purpose, that service, that that extension of oneself for others. And ultimately, I can agree with you more. I genuinely believe that purpose, you know, I was saying, I was speaking to a friend recently. I was saying how, you know, a dream without service is incomplete. Like, the idea is like, you know, you can only build a dream so far with the desire for it to all be about yourself. And then it doesn't even do it for you anymore. And I feel like, but you've paved a really good path because also you can't just jump

• 1:01:59Jay Shetty?

  to being heroic because there are certain skills and muscles and and things that you develop on the way by building courage first. Like, there are certain tools and and tricks and tips and things that you pick up along the way that make it more powerful to be heroic after.

• 1:02:16Ryan Holiday?

  Well, one of the things I was inspired by, it's just something I ran in a small news story many years ago, was the decision, I think that maybe 10 years ago, that CVS just decides they're going to stop selling cigarettes. Now, this is bad for CVS, this is bad for the shareholders of CVS, but it's obviously good for the world, right? And as they find, overall cigarette consumption goes down across the entire country because people are just like, it's harder to get cigarettes, they just smoke less, right? And so, like, obviously, we love ambition, we love creativity, we love people who are trying to be successful. But but there is something beyond that. I think we saw it during the pandemic, the people who showed up every day for work, even though it must have been scary and terrifying for them, but they knew that other people

• 1:03:01Ryan Holiday?

  were depending on them, that where would we be without those kind of people? And so, you know, obviously, the pandemic revealed some selfishness and indifference and and all sorts of awful parts of our modern society, but it also revealed, I think, some of the best of our society. And I wanted to celebrate this idea of Of yes, pushing through fear is important. But why are you doing it? Right? Who are you doing it for? That really, really matters.

• 1:03:33Jay Shetty?

  Yeah, I think that's beautiful, man. Ryan, this has been such a wonderful conversation. I highly recommend everyone. If you haven't read Ryan's work, I mean, I would go and buy every single book and I'm not kidding. They not only look beautiful, but they are beautiful. And you know, obstacle is the way is is just fantastic. Ego is the enemy. Stillness is the key. We talked about last time. I mean, and this one courage is calling is what we've been talking about today. Ryan, we end every interview with the final five. You've done this before. These are the fast five. So every question needs to be answered in one word to one sentence maximum. You are the writer, so you can help me define what one sentence counts as. Like, how many words are in a good sentence, Ryan?

• 1:04:17Ryan Holiday?

  As many or as few as there should be.

• 1:04:21Jay Shetty?

  Okay, all right, great. I love the vagueness of that. Okay, brilliant. All right. So the first question for you is, what is something you once were attracted to? But it's become less important to you?

• 1:04:36Ryan Holiday?

  I think money, certainly money. I think money represented something to me early in my life. And the more you get of it, the more you realize that it really doesn't mean anything. And there's less to do with it than you think there is.

• 1:04:53Jay Shetty?

  Right. And did that come after a certain amount of success? Did that, where did you feel like? What made you feel that? It doesn't have to be a statistical number. I just mean, like, what was it that made you feel that way?

• 1:05:05Ryan Holiday?

  I don't know if there was a specific number, but I remember I had a conversation with Tim Ferriss once, and he was like, what do you do with your money? You know, and he's like, I was like, what do you mean? He's like, do you have a speedboat? You know, do you invest it? What do you? And I was like, it just goes in the bank, right? Like, I don't know. And he's like, So it's not important to you, really? And I was like, yeah, I guess not. You know, he was like, his point was if you're, if you don't need the money, just make sure that you're not saying yes to things that you don't really want to do to get more money if you don't really want the money. And that was very helpful to me.

• 1:05:38Jay Shetty?

  Yeah, I love that. Okay. Question number two. What is something you were first uninterested in that has now become something intriguing or a curiosity?

• 1:05:48Ryan Holiday?

  I mean, I, I think I always knew I wanted to have kids, but I didn't understand just how much I would love it and how, how much it would transform my life. And so I would say, you know, sort of family being the, the sort of big, big thing. Especially again during the pandemic, just it was like, oh, this is all I really care about. This is all I'm going to focus on. So, so maybe family would be the big thing.

• 1:06:16Jay Shetty?

  I love that. All right. Question number three. What's the most used piece of Stoic wisdom that you utilize on a daily or more regular basis?

• 1:06:25Ryan Holiday?

  The first Stoic exercise is this idea that there's things that are up to us and things that are not up to us. And really, all we should focus on is what's not up, is what is up to us. And that's extremely hard to do. And I screwed up all the time, but I find myself constantly reminding myself, it doesn't matter. No amount of thinking about this will change it. Just focus on what you can do in response to it or, you know, inside of it. That's probably.

• 1:06:54Jay Shetty?

  I love that.

• 1:06:55Ryan Holiday?

  Ironically, the most basic thing is the most complex thing.

• 1:06:58Jay Shetty?

  Absolutely. Well, I was going to ask you that as the next question. What is a piece of Stoic advice that you think you're still wrestling or grappling with that may be counterintuitive? It may even be off the wall. And you may be like, okay, this is one of those things that you leave out of the book because it's just, it just, you know, and there's plenty of stuff with that in the Vedic tradition, too. Like there's some stuff that's just off the wall. Is there something like that from the, that you've been reading recently that?

• 1:07:22Ryan Holiday?

  I mean, I think all of it, to be perfectly honest, all of it is on a day to day basis. But there is a line in, in the beginning of Meditations, Marcus Aurelius lists all these things that he learned from his mentors. And I think it's from Sextus or Severus, someone early on in his life. He said that I learned how to be free of passion, but full of love. And that doesn't, that doesn't sound very stoic, right? The idea of being full of love, the being free of passions sounds very stoic, but full of love sounds more eastern and/or Christian, a little bit of both. And I, I find that to be very beautiful. And the idea of being like, okay, I'm gonna strip out some of the emotion.

• 1:08:05Ryan Holiday?

  I'm gonna strip out some of the need to control, blah, blah, blah, blah, blah. But I'm gonna replace it with like, love, empathy, kindness. That is harder for me to do, but, but something I'm, I'm working on.

• 1:08:17Jay Shetty?

  I love that. That was, that was beautiful answer. Okay, fifth and final question. What are your top favorite? I don't mind how many numbers you, three, four, five books that you've read this year. So more recent or that you've read this year. It doesn't even have to be a recent book.

• 1:08:34Ryan Holiday?

  Dr. Edith Inger wrote this book called The Choice. She's a Holocaust survivor. I loved that book. It blew me away. Then there's this other little book by Viktor Frankl that they found recently called Yes to Life.

• 1:08:47Jay Shetty?

  Oh, wow.

• 1:08:48Ryan Holiday?

  In spite of everything. It's like a collection of some of his lost lectures that I really, really enjoyed. And then I read this book, it doesn't have a great title, but it's, it's sort of changed how I've been thinking about things lately. It's called Indian Givers. And it's about what Western society owes and has learned from indigenous peoples over the last like five, 600 years. And it was an incredible book that like, it just didn't, I just had no idea. This isn't unfortunately what we teach in schools. And I, I've just been thinking about that book so much. I really, really liked it.

• 1:09:28Jay Shetty?

  I love that. Beautiful. Three that I haven't read. So producers, Amazon order those books for me right now. I need, I need those books. And for everyone who's been listening and watching, as you know, I've been talking to Ryan Holiday. I want you to go and grab a copy of Carriage is Calling. And like I said, every other book, you can find Ryan on the podcast. He's one of the few guests who've been on the podcast twice. This is his second episode and of course. Ryan, it's always a joy to have you on. I hope we get to do many, many more of these. I hope we get to go on many, many more walks. I really do hope we can spend a bit more time together. I've never been to Austin. Can you believe it? You have to come. I also need to come out to Austin. But thank you for making the time. Thank you for being so generous.

• 1:10:10Jay Shetty?

  Everyone who's been listening and watching, make sure you tag me and Ryan on Instagram, on Twitter. Let us know what resonated with you, what connected with you. If you've read one of the books that Ryan recommended, come back and tell him about it. Like, we want to hear that. And I love staying connected to this community. So thank you to our On Purpose community. Thank you to Ryan Holiday. Appreciate you, man. Thank you so much. You're the best.

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