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, 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."
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.
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 best-seller status, and Stillness Is the Key appears in more than 40 languages, and all of his books have sold more than 4 million copies.
Together they've spent over 300 weeks, 300 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, uh The Painted Porch, uh and sits on the historic Main Street in Bastrop, Texas.
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.
Uh 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 uh 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, uh societal level for I've seen you do a lot of activism work, too.
But, Ryan, welcome back to the show.
No, thanks for having me.
And it 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 uh 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 uh I hope that's encouraging to people cuz it it it it's amazing.
Uh 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 at American Apparel.
And then, I also remember talking to you about how you're the Leonardo DiCaprio of writers, where you you'd written all these amazing books that were epic.
And you were waiting for this, you know, the arbitrary idea of ranking on a list and I you know, I 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 place 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 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 10,000 hours, right?
It takes 10,000 hours to get to mastery.
I I think two things are easy to miss.
There number one, um it's not 10,000 hours of 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.
Um 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 ninth and the eighth.
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. 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?
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 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 you know, I think we we thought it would be a project that would take a year and it took 2 years.
Uh 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 cuz 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 It was a very trying and challenging experience, to be sure, but the upside was that it made the rewards of it so far, you know, much more compelling and and meaningful, I think. Yeah, I love that.
It's wonderful It's wonderful hearing that, you know, you've got through and and and you figured it out and I'm sure it's been harder than it needed to be, but it it sounds wonderful and I I hope I get to 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 I really look forward to mean books are so 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.
Um a bookstore in 2021, let alone during a pandemic, is, you know, like uh not not not the best.
Um but I think, you know, I have a podcast, too, and and there's something amazing about reaching millions of people at scale digitally throughout the world.
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 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 the smaller amount of people that you are reaching.
Yeah, I 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 in 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 was beautiful.
Like it's 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 and people are like actually everyone's going to be like, what are you guys doing?
Jay's just having a conversation which is partly what I'm doing.
But I want 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 and why you felt compelled to share it 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 and then there's this kind of moment where you go could I do that for someone else?
And then we're 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 Loveline.
Now he has a wonderful podcast as well and he was speaking and I had grown up listening to Loveline.
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?"
Cuz 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 it may 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 the stuff that, you know, it'll be like a 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 Epic tetus, who is this Roman slave.
And I And I went back to my hotel room and I bought Epictetus and I bought Marcus Aurelius cuz I'd seen the movie Gladiator.
And uh And And these two books arrived and they they hit me I 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 awaken 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 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 going to be, but that he couldn't let this change him or make him angry, and that then 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.
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 Aurelius 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 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 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 that 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, "Oh, 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."
Well, the crazy thing about the book question is um 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, uh I'm struggling with depression.
What's a book you would recommend?"
And I would like took me 2 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 I if that's an easy way I can help a person, but the crazy thing about the Dr.
Drew story was like 3 months later, I went to a different conference and he was there again.
I don't know how I I don't know how the 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 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 um the amount of people that like ask me for recommendation versus the amount of people I hear back from who have actually taken the time to read the book, you know, is is it's a 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.
Um they're there, but no one can read them for you. 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.
Uh 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 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.
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, uh or, you know, it's not just physical danger, um 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.
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.
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 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.
Um every 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 I'm thinking about that right now and I hope everyone who's listening or watching is thinking about that, too.
I I can't think of I can barely think of anything if if anything at all.
And so, you know, that aligns very strongly.
And I 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 you know, a message, an email.
Walk us through Why is it that we take unaccountable, faceless strangers so seriously?
Like why does that exist?
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 I shouldn't like you know, like or or you spend to 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 Did the publisher like it?"
You know, it you 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 and yet we hand over approval, success to other people.
And like look, when when The Obstacle Is the Way came out, um just just to just to sort of illustrate this idea that nobody knows anything.
Um, 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.
Um, 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 best seller list the week it came out, it sold like maybe 30,000 copies in the first 6 months, maybe 60,000 in the first year.
Um, 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, uh about a million and a half copies.
So, the success of that book, if I was judging it based on what other people said, um would have been a failure, would have been a disappointment, would have been uh mediocre at best.
Um, 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, um 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 the 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 going to 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, uh which is a 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.
Yeah, I know 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 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 2 years my life was hell because everything I did was massively criticized because it wasn't as good as the previous president.
And so and I was a I didn't knew nothing about leadership.
I mean, you know, leadership is a really big, complex, uh conscious, thoughtful thing.
I was 18, didn't know anything.
Anyway, for 2 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 going to 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 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 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? 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 un undeservedly.
Um Marcus Aurelius talks about being able to accept success without arrogance, and let uh 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.
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 going to 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 the 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 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 so Ryan, then what do we do with fear?
If everyone's listening and watching, they're they're going through the fears that we 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 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 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 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 I was afraid of what might happen.
And I remember one of my mentors goes, "You know, um 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 5 years instead of 4 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 it that was really important, right?
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 the 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 that fear because we have a rational understanding of it instead of this sort of irrational emotional understanding 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 you're almost laughing at yourself.
Like, how how was that the thing that held me 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 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 cliché about do one thing every 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, uh but I'm going to do it anyway.
Um 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 uh 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 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, Tik Tok's this thing.
Now I can you know, you're what you're cultivating is the ability to be comfortable being uncomfortable Yeah.
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 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 2 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, 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?
Well, this is the paradox, right?
We tell ourselves like, I can't do it now.
I'm going to wait till I'm more financially successful.
I'm going to wait till I'm more well known.
I'm going to 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 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 start" But no, now you don't want to lose 10 years of work, right?
You'd think that finance 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.
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 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?
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 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 going to be too comfortable.
And so, you you you kind of have to see that comfort, that that like taking it for granted-ness as the enemy because it's it's what makes you afraid.
You don't want to lose it.
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 worked 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 You're playing 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 aides says, you know, maybe you should wait till after re-election.
They say this could be bad.
You know, it's going to be risky politically.
And he says, "What the hell's 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 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, you know, 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 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.
And I 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 the test I have is am I being a good steward of that philosophy?
And so, if 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, not is this going to win me the most friends. Yes. Yeah, absolutely. Yeah, no.
And 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 yours and you've known that from day one, but you know, it's like for me when I see other people who I believe 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 you know, like maybe they see us competition."
And I was just like, "Well, why would I compete with someone who's try 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 I requires a certain amount of courage in 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.
Um 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 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 uh 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, um 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 in themselves, uh the more helpful they can be to other people, and then ultimately the more impact everyone can have together. Yeah, absolutely.
I I love that because I was 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 and what you were sharing from 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 I 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.
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.
Uh 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.
Yeah, there's a great joke that I heard that that envy is the only sin that isn't any fun. Uh yes. Right? Like uh sex is fun.
Uh even overeating is fun, right?
All most of the deadly sins are at least fun while you're doing them. Envy sucks.
No one is having less fun than the person who is being eaten up with envy and jealousy. Yeah.
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.
Um 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 isn't that fun.
And it doesn't get you what you want, you know?
Um being being bitter, being resentful, being closed off or selfish, it's it's not fun. Totally.
And 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 that's something that could I I have no idea.
That's not a, you know, 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 often times, 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 I think often times 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 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, uh what you have, that that's that's another big part of it the Stoics talk about like how jealous you would be of yourself if you didn't have those things, right? Yeah.
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 I wonder from you, what is something currently that the two questions here I'm going to ask both of them now and then you can take them.
What what is the thing that you've been in the last 12 months fearing the most?
What 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 I think I'm I have easier time answering the the first one than 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 this is a big Stoic concept is like just how much is out of your control. Right?
Like uh you care about these people, this thing more than anything in the world and 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?
Uh 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.
Um and and and so I think, you know, when we talk about uh parenting, I don't think we talk about courage enough. Right?
So first off, just to be a woman who 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 I think we we've gotten so used to it or perhaps we we just don't think about what a insanely courageous act it is.
But then to be a parent in this sort of crazy messed up world, uh 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.
Um it's been uh 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 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 going to 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. Yeah.
And do you do you genuinely believe and of you know, pandemic aside of course because that that's a huge, huge, huge thing that obviously affected everyone on the planet, but do you genuinely believe that a disruption of plans has led to better plans, results, ideas, innovation, inventions?
Look, uh 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 a enormous forced lifestyle experiment.
We had to reimagine a lot of things.
We probably wouldn't be doing this remotely, uh you know, if it weren't for the pandemic.
You know, there's things that you 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 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.
Um I I think coming out of the pandemic, I'm not going to travel nearly as much.
Not for safety reasons, but just realizing, oh, um I've been going a mile you know 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 it's not that the Stoics 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 manage 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 The third part of the book is the heroic.
And and I find this and I love that it's obviously towards the end, but it's it's uh 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 or you know, for people the girl or that person in in the ad, in the movie, in the book, in the story.
Uh 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?
So if we think of courage as the triumph over fear, I maybe what we're saying is that heroic is something beyond even that.
So uh in the book I'm talking about Michael Jordan's decision to leave basketball to play baseball.
That's an immensely courageous thing cuz it's risky, people are critical of it, he's no idea if he can go from being the best in the world at one sport to 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. 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 is pushing past doubts or risk or whatever.
But, the what about the courage to leave a successful business to start a non-profit, 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.
And it's heroic because uh by by putting others above us, we're actually elevating all of us.
And so, uh I wanted to look at 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 it 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 I can't agree with you more.
I genuinely believe that purpose, you know, I I was saying I spoke 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 and then it it doesn't even do it for for anymore.
And I 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 and things that you develop on the way by building courage first.
Like there are certain tools and and and tricks and tips and things that you pick up along the way that make it more powerful to be heroic after.
Well, one of the things I was inspired by it's just something I read in a small news story many years ago was the decision, I think 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 the like obviously we we love ambition, we love creativity, we love people who 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 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 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 they not only look beautiful, but they are beautiful, and uh you know, Obstacle Is the Way is is just fantastic.
Ego Is the Enemy, Stillness Is the Key we we talked about last time.
I mean uh and this one, Courage Is Calling is what we've been talking about today.
Ryan, we end every interview with a 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 sent in a good sentence, Ryan?
I as many or as few as there should be. Okay. All right, great.
Uh I love I love the vagueness of that. Okay, brilliant.
All right, so the first question for you is uh what is something you once were attracted to but 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 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 and did that come after a certain amount of sense success?
Did that come Where did Where did you feel like what made you feel that?
It doesn't have to be a a statistical number.
I just mean like what 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 Ferriss once and uh he was like, "What do you do with your money?"
You know, he's like I was like, "What do you mean?"
He's like, I He's like, "Do you have a speedboat?
You know, do you invest it?
What do you I don't know."
He's like, "It just goes in the bank, right? Like I I don't know."
And he was 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 then that was very helpful to me. Yeah, I love that.
Okay, uh question number two.
What is something you were first uninterested in that has now become something intriguing or a curiosity.
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 imp- how much it would transform my life.
Uh and so I would say uh you know, sort of family being the the sort of big big thing uh especially again during the pandemic just it was like, "Oh, this is all I really care about.
Uh this is all I'm going to focus on."
Uh so so maybe family would be the big thing. I love that.
All right, question number three.
What's the uh 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 up is what is up to us.
And uh that's extremely hard to do and I screw 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.
Uh that's probably I love that.
Yeah, 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 like 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 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.
I think it's from Sextus or Severus or 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 that doesn't sound very stoic, right?
Um the idea of being full of love.
The The being free of passion sounds very stoic, but full of love sounds more Eastern and or or Christian uh a little bit of both.
And I've I've I found that to be very beautiful.
And the idea of being like, "Okay, I'm going to strip out some of the emotion.
I'm going to strip out some of the need to control uh blah blah blah blah blah, but I'm going to replace it with like love, empathy, kindness."
That is harder for me to do, but but something I'm I'm working on. 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 or that you've read this year.
It doesn't even have to be a recent book. Uh Dr.
Edith Eger uh wrote this book called uh The Choice.
She's a Holocaust survivor. I loved that book. I I it blew me away.
Um then there's this other little book uh by Victor Frankl that they that they found recently called uh Yes to Life Oh, wow.
um in spite of everything.
It's like a collection of some of his lost lectures uh that I really really enjoyed.
Um and then I read this book.
It doesn't have a great title, um but it it's it 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 Wow.
over the last like 5 600 years.
Um and it was an incredible book that like just didn't I just had no idea.
This is isn't unfortunately uh what we teach in schools.
Um and I I 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, uh producers, I'm going to 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 Courage 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? So, 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.
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 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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