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 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. Hey, everyone, Welcome back to un Purposed, 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 half Post back in like twenty sixteen, when I was just starting a lot of my online work.
Then we did in Nazadac Reads probably around twenty seventeen, maybe twenty eighteen, 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. 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 I have all reached number one New York Times best seller status, and Stillness Is the Key appears in more than forty languages, and all of his books have sold more than four million copies. Together. They've spent over three hundred weeks three hundred weeks on the best seller 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 sits on the historic main street in Bastard, Texas. And his new book, The Courage Is Calling already in 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 broughte 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 now. 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 get 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, 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. Absolutely. Yeah. I remember talking to you about like, you know, you started in marketing, and you know, you talk about your time that American apparel, And then I also remember talking to you about how you're the Leonardo DiCaprio right is where you've 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 tons and only one once and that's pretty much the same as you. 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 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. Well, you know people talk about like ten thousand hours, right, it takes ten thousand hours to get to mastery. I think two things are easy to miss. Their number one, it's not ten thousand hours of terrible, grinding labor. It should be fun. And I had a
ton of fun along the way too. Just because it might take ten thousand hours or it could take twenty thousand hours or one hundred thousand 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 twelfth book. I'm proud of all the books in between, but the twelfth book is only possible because of the eleventh and the tenth, and the ninth
and the eighth. 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 you're you're having fun along the way, as you said, absolutely, And I wanted to start off somewhere before we dive into all the wisdom and the insight and the practice is I wanted to know what does it feel like as an author during the pandemic to have opened your own bookstore called the Painted Points
like that 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? Well, it was very exciting at first. 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 twenty twenty, 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 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 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 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, 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 now 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 loved I mean, books are such an
amazing thing. Like if you think about what a book is, right, like a book is ten years or a lifetime of work and understanding bound between two covers for like twenty dollars, 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 twenty twenty one, let alone during a pandemic is you know, like 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. But there is also something special about holding things and having a space,
and so I just 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 could be fun could also be a business opportunity, But you know, I think improve the community in which we live. And that that's kind of what I've just been thinking about out more lately, is like, not everything has to be like how do I reach as many
people as possible? It could also be like how do you really reach the people the smaller amount of people that you are reaching? Yeah, I count 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 which is ten faces every single week was beautiful, Like it's it's
been some of the most meaningful work I've ever done, and you're spot on, So I get that. Now I want to start. I've got so many questions to ask you run so, and we've just been chatting so and to like, actually, everyone's gonna be like, what are you guys doing? Jays 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 I wanted to understand, like, can you tell us the story of how you discovered stoicism and how that first moment made you feel and why you felt compelled to share with the rest of
the world. 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're talking about skill earlier, how did 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 doctor Drew from from HLN and from love Line.
Now he has a wonderful podcast as well, and he was speaking and I had grown up listening to love Line, and so 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? Because 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 be like skipping all the stuff that you know. It'd be like a It's like getting you know, notes from from from people ahead of you. And so um I asked him, and he told me he was reading
the writings of Epictetus, who is this Roman slave. And I went back to my hotel room and I bought Epictetus and I bought Marcus Surrealius because I'd seen the movie Gladiator and h and these two books arrived and they they hit me. I read Marcus Arelius first. Actually here, let me grab this is mine now, fifteen year old copy of Meditations. I've had to retape the cover on because I've read it so many times. But but you know, you read Meditations, and it just 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. 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 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 going to 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 I remember I was taking philosophy classes at the time, but it was nothing like this, 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 rus 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. Yeah, I love that. Thank you for sharing that so much, 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 ninety nine percent of people don't go up, and the one percent 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 ninet nine percent of the time is I don't think I have time for that, Like I'm not sure that's going to 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. You would never get time and access to someone that inspires you in that way. And thank you for 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 how you feel. Straight away you go, I want to live like that. 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 forty days live and twenty million of you tuned in. Now I am taking that same focus, that same presence to Calm. I've partnered up with Calm to release a new series called The Daily J 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 Nowtcalm dot com forward slash J to get forty percent off a premium membership. That's Calm dot com Forward slash J. 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 saw 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 took me two seconds to reply, right, And like that, 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 doctor 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 odds of it worked, but I went up to him and I was like, you probably don't remember me, but I read those books, right, 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 twenty years later, fifteen years later, 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. Yeah really, well, I said, And this leads us nicely to courage is calling that 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 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 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 it's also just Will you make an important point about courage which I really tried to build a 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 a courage 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, Like, 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 true try something, not because they're afraid of failing, which they probably are, but also just afraid of of success, right, like a afraid of 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. Fear is the thing that gets in the way what Stephen Presfield 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 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. 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 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 you know, a message and email. Walk us through why is it that we take unaccountable facing the stranger is so seriously that why does that exist? Look, it's not like this just some modern thing. Right. In Meditations, Mark Surreali says, the crazy thing is we all love
ourselves more than other people. We're all self interested, selfish people. It's 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 way, you know, this is why you do what you do, and yet we hand over approval success to other people, and like, look when when the obstacle is the way it came out 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 Obstacles the Way, and the publisher said that idea is half as good as your last idea. They like, they did not believe in it. Look, they believed in it enough to purchase it, but they did not have high hopes. A close friend of mine I found out later predicted that it would sell five thousand
copies right it came out. It didn't hit the best seller list. The weekly came out, it sold like maybe thirty thousand copies in the first six months, maybe sixty thousand in the first year, did not hit a best seller list for the first five years of its existence, and then ultimately has 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 and 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. And then three it was pleasurable and exciting and rewarding for me to do, and so kind of everything beyond that was extra and 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, 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, you know, and 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 going to get it at first. 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 allows you
to sort of ignore both of those things. Yeah. No, that indifference I find so fascinating because when you first hear it, it sounds like there's no fun, and it sounds like there's no joy, but actually when you live it, it's liberating, and I find that there's something really fascinating. I remember first coming across that when I was around probably like twenty years old. I was the president of a youth organization back in London, and I took on
this role at about eighteen years old. I was given it. I didn't audition for d didn't apply for it. I was given it. And for two years my life was held because everything I did was massively criticized because it wasn't as good as the previous president and so. And I didn't knew nothing about leadership. I mean, you know, leadership is a really big, complex, conscious, thoughtful thing. I
was eighteen, didn't know anything anyway. For two years, everything I did was criticized, it was really cuted, it was compared, and I started to feel really bad about myself. But the one thing I held onto was that everyone's criticizing me for my management, but not for who I am. 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 said I'm a bad person. I'm going to hold onto that. And then something really
fascinating happened. We had a fundraiser when I was about twenty years old, and that fundraiser, I like outperformed where I've raised lots of money for this really important foundation and all this, 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 it's still now to anyone 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? Yeah? Totally. It's kind of similar to 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 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 worse, right, like being attacked undeservedly. Marxurrealiz 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 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 the you know 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, 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 it is identifying with the hot streak that they're on, well, statistically that's just not gonna last, right, And so you have to become you have to understand that you're gonna lose, that you're gonna miss, you're gonna screw up, and you if you're in a place where you identify with those
external results, you're you're really really vulnerable and you're going to be really unhappy, especially in those dark, those dark, dark moments. Yeah, so Ryan, then what do we do with fear? If everyone's listening and watching that 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. Well, the Stoics obviously believe in the power of reason, right, and a lot of fear
you can 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 Stokes would say is what if that happens? Like, what does it actually mean? Right? Not like oh this 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 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 that was really important, right, to break down the thing that you're afraid of, to really think about the worst case scenario. Right, people are afraid of 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 someone's telling me to jump off of. 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 can't afford to lose this. But most of the time we break those fears down, and then we're better able to manage that fear because we have a rational understanding of it instead of this
sort of irrational emotional understand standing of it. 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're almost laughing at yourself, like, how
was that the thing that he would be back. 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 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 not do the thing now, you actually have less information about how the world works. And so you know, there's that sort of cliche about do one thing free day that scares you. It's actually pretty good advice. Right, You're sort of building the muscle, You're building that ability to override the This seems scary, but I'm going to do it anyway. I think cultivating that ability to sort of push through
that fear is really important. 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 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, and 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 You know, what you're cultivating is the ability to be comfortable being uncomfortable and knowing that you'll figure it out and eventually get comfortable again. 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 the courage, it's so easy to get comfortable again. Like, it's fascinating, isn't it. Like 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 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 settled 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 something that you've
seen others do that you've spoken to on your podcast. 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, and wait till I'm more well known. Nona, 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 ten years into this company, then I'll
put out this new idea. Then I'll but no, now, you don't want to lose ten years of work, Right. You'd think that financially the financially successful people would be the most comfortable taking the risks. But they have 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. 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, but 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 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 make me angry or whatever? And look, I didn't cultivate this platform to not say what I think. Right, Like, the job is not having the platform. The job is
not this or that. The job is doing the thing right. Is 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 going to 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 going to do it because then
you're gonna be too comfortable. And so you kind of have to see that comfort that like taking it for grantedness as the enemy, because it's it's what makes you afraid. You don't want to lose it. Yeah, I'm so glad you said that. And I went through something similar recently 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 trying new things out, because what was the point otherwise I'm already living in bonus Land, right, like I'm ready with house money. 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 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. Yeah. There's a great story about Lyndon Johnson when he proposes passing the civil rights legislation and one of his aid says, you know, maybe you should wait till after reelection. They say this could be bad.
You know, it's going to 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 that's how seductive it is.
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 going to do what I care about, what I like, what I love, what I think 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 twenty five hundred or so years 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 the test I have is am I being
a good steward of that philosophy? And so if I'm afraid to be the same thing for the presidency, You're not. You don't own the presidency. You're just the guys 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 not? Is this going to
win me the most friends? Yes? Yeah? Absolutely? Yeah no, And I think I ask a very similar question, Like for me, it's you know, it is servitorship. 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? 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 yous and you've known that
from day one. But you know, it's like for me, when I see other people who I believed to positively impacting people's minds, I want to collaborate, connect do more together because I feel like we need more of that. And I was speaking to my team recently because I was talking about collaborating with someone and they were saying, well, Jay, you know like maybe there, 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. Well, this is another thing. I think it 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 into like this is about my career, it's about my success, is about my family, right, it's about my business. 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 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 books that I've loved, and I've done that now for since I don't know, twelve thirteen 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 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 it's 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 in themselves, the more helpful they can be to other people, and then ultimately the more impact everyone can have together. Yeah. Absolutely, I
love that. Because I was sharing it 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 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 sort of unhealthy trait that comes out. And if you study someone, then you appreciate, you, admire, you, honor. And I know that in my life I would rather live with admiration on an 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 where you're doing. You're studying their life, sharing your study and your notes with us. 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 I think that's where people don't recognize
that that collective good is always better than individual success. Yeah, there's a great joke I heard that that envy is the only sin that isn't any fun. Yes, 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. Yeah, envy sucks. No one is having less fun than the person who is being eaten up with envy and jealousy. And so the decision, and it does have to be a decision, because I think there's probably
some evolutionary reasons why we feel envy. The decision to say, like, I'm just going to be happy for people. I'm going to help other people. I'm going to help other people and not ask for anything in return. I'm just going to try to put good stuff out in the world. I'm going to try to use my assets to help other people, and I hope other people do the same. But I'm not going to 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 bitter, being resentful, being closed off for selfish, it's it's not fun totally. And and if and according to your line of thought, which I 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 that's something that could I
have no idea. That's not a you know, 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. 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 it's actually fun to be them, right, Like, I think oftentimes we'll look at something that someone has and we'll 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 tradeoffs 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 that's another big part of it. To stoves talk about like how you would be of yourself 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. Yeah, for sure, I wonder from you, what is something currently that the two questions here, I'm gonna ask both of
them now and then you can take him. What is the thing that you've been in the last twelve months fearing the most? Is 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's personally the most courageous thing that you've done recently? And it doesn't have to be huge, right, Like, that's the point. I think I have easier time answering the first one
and the second one. But I have two young kids, and so you go through something like this pandemic, what you're really forced to grapple with, and there's a big 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, and yet you don't control it. Right.
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 eighteen 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 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. Like I think we've gotten so used to it, or perhaps we just don't think about what an 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, when we think about what Buddhism is, or or or any of these philosophical schools, they were designed precisely for these kinds of events, 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 managed to be happy and
productive and and you know, not a wreck inside of them. Yeah, And do you do you genuinely believe and of you know, pandemic aside, of course, because that'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. Look, no one would say, like, hey, in America, you know seven hundred and fifty thousand 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.
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 a mile a minute for thirty 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 it's not that the Stokes would say that everything terrible has something 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 managed to excavate little bits of positivity or opportunity for progress. And that's what the obstacle is. The way is really about. 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 would 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 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? 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 critical of it is no idea. If you 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 w NBA 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 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, uh, 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 not putting yourself often physical danger, but you're putting your interests behind the interests of other people. And that's a very scary, difficult thing to do. And it's he wrote, 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. Yeah, I deeply appreciate that definition.
Thank you for sharing with us, because to me, that that journey from courage to being heroic, that 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 suppose
I was speaking to a friend recently. I was saying, how you know a dream without service is in complete, 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 to being heroic, because there are certain skills and muscles and things that you develop on the way by building courage first, Like, there are certain tools and tricks and tips and things that you pick up along
the way that make it more powerful to be heroic. Aft. 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 maybe ten years ago, that CVS just decides are going to stop selling cigarettes. Now, this is bad for CVS, this is bad for the
shareholders of CPS, 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 smokes, right, and so like, obviously we love ambition, we love creativity, we love people who are trying to be successful. 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 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 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? 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 just fantastic. Ego as 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 writers, so you can help me define what one sentence counts as, Like, how many words are in a sense in a good sentence? Ryan? I? As
many or as few as there should be? Okay? All right, great love. 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 that has become less important to you? I think money, certainly money. I think money represented something to me early in my life.
And the more or 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, right, and and did that come off to a stain amount of sainse 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. I don't know if there was a specific number, but I remember I had a conversation with Tim Ferris once and he was like,
what do you do with your money? You know? And he's like, what do you mean? He's like, 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. Yeah, I love that. Okay. Question number two, what is something you affect uninterested in that has now become something intriguing or a curiosity? I mean, 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 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 maybe family would be the big thing. I love that, alright. Question number three, what's the most used piece of Stoic wisdom that you utilize on a
daily or more regular basis? 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 is what is yes, 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 I love that. Ironically, the most basic thing is the most complex thing. 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 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 the stuff the wall. Is there something like that from the that you've been reading recently that 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 the beginning of Meditations Mark Surrealists lists all these things that he learned from his mentors, and I think it's from Sextists or Severist someone early on in his life. She said that I learned how to be free of passion
but full of love. And that doesn't that that doesn't sound very stoic, right, Um, The idea of being full of love, the being free of passions sounds very stud but full of love sounds more Eastern and or Christian, a little bit of both, and I find that to be very beautiful. And the idea of being like, Okay, I'm gonna strip out some of the emotion, 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 working on. I love that. That's that's beautiful and sat okay. Fifth and final question, what are your top favorite I don't mind how many numbers, three, four, five books that you've read this year, so more recent or that you've read this year. It doesn't even see a recent book. Doctor 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 Victor Frankel that they found recently called A Yes to Life. Oh wow, in spite of everything. That'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 six hundred years. And it was an incredible book that like, it just didn't I just had no ideas. Isn't unfortunately, what we teach in schools and I've just been thinking about that book so much. I really really liked it. I love that beautiful three that I haven't read. So Produces Amason
order those books for me right now. I need those books. And for everyone'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 couragees Core, 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 a 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 you 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? So I also need to come out to Austin. But thank you for making the time. Thank you for being so generous. Everyone who's been listening on 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.