#128 Ryan Holiday: A Stoic Life
01:09:19 Share

What I love about Stoicism, what gets me excited about it is that all of the Stoics were active elite professionals at whatever they did. And Stoicism was a guiding force, a thing that allowed them to do that. To me, what I love about Stoicism is that it's very much philosophy for the world. I mean, it's literally founded, one, by a merchant who loses everything in a shipwreck.

And two, it's founded in the Athenian Agora, like in the center of Athens, in the marketplace where it's battling from day one, limited attention from busy people who have actual lives.

Welcome to the Knowledge Project Podcast. I'm your host, Shane Parrish. This podcast sharpens your mind by helping you master the best of what other people have already figured out. If you're listening to this, you're missing out. If you'd like special member-only episodes, access before anyone else, transcripts, and other member-only content, you can join at fs.blog.com. Check out the show notes for a link. Ryan Holiday is here today.

Ryan is a prolific author and modern philosopher. His books include The Obstacle is the Way, The Daily Stoic, and most recently Courage is Calling. I wanted to talk to Ryan not only to learn more about Stoicism and deepen my understanding, but to also learn more about his process for writing and reading. We talk about how he writes a book a year, how Stoicism can help us make better decisions, the value of journaling, and the four virtues, courage, self-control, temperance, and justice.

It's time to listen and learn.

The IKEA Business Network is now open for small businesses and entrepreneurs. Join for free today to get access to interior design services to help you make the most of your workspace, employee well-being benefits to help you and your people grow, and amazing discounts on travel, insurance, and IKEA purchases, deliveries, and more. Take your small business to the next level when you sign up for the IKEA Business Network for free today by searching IKEA Business Network.

Let's start with your book writing process. You're prolific, man. You do like a book a year. How do you do that? What's your process for writing? What does that look like? Take us inside and behind the scenes. It's weird because obviously I sort of know objectively that I'm prolific and people tell me that I'm prolific. But to me, I am more curious that other people are not so prolific. I mean, I realize that different authors do different kinds of books. But I do feel like if this is the job and you're waking up and thinking,

doing it every day, it does seem to me that like more published work for people should come out of the other side. But I am kind of amazed. Maybe it's because writing is a creative profession that people don't treat like professional sports or, you know, trading or anything where it's just sort of excused, like because people think it's hard and they don't understand how it works.

They're just really tolerant of sort of spotty output. Do you know what I mean? Yeah. The biggest part of my process, and this is probably boring and unsexy, but it's like,

I show up and write every single day. And if you show up and write every single day, pages come out of the other side of that. There's a couple parts of my process that are integral to the output that I have, which is one, I always have the next idea set before I finish the one that I'm on. So there's not this sort of like existential angst about like what I do next. Again, likening it to sports, like,

They know the season starts at the same time every year and that there's always another year unless you retire. So it's not like,

should we get a league together this year? You know, like, should we play this year? It's like, I know I've got the next project. And there's usually a contractual obligation slash like deadline for that project. So that keeps me really honest. I'm also always like reading. And so the reading is creating the material, which is then setting up the next book. So I kind of have this system that is just like,

in motion all the time. And I'm like a part of it. When do you read? Like, do you read in the afternoon? Do you write in the mornings? Are you always writing at the same time for the same length of time? Like how regimented is that? If you'd asked me before COVID, I would have said like, I read a lot on airplanes and in hotel rooms. Like I tended to, I wouldn't do anything but like read when I was traveling. And

And that's where I made up a lot of it. And then when COVID happened and now it was like, oh, actually you have to integrate this a little bit more into your regular life. It's been a bit different. And I wouldn't say it was a struggle. Obviously early on in the pandemic, I got tons of reading in because there was like nothing but time. I would say like lately I've been,

trying to figure it out a bit more, I've been kind of out of a rhythm, which I guess would be another point, which is like, for me, I am just generally more of a binge reader than a like, I do 200 pages a day or something. Like, if I'm like, finding awesome books in a row, I might be banging them out like that. And if I'm like,

You know, you pick up a book and you're like, this is okay. And I know I want to read this, but like, it's, it's a bit of a chore. Then that can like grind the whole thing. And if you get a couple of those in a row, suddenly you're like, am I good at reading anymore? You know? Yeah.

A couple big parts of my reading routines. I read while I eat lunch. I'll read for like 45 minutes or an hour. So I read then. I usually do read in the afternoon and then I read before bed. And then on the weekends, I tend to read.

So when do you write? Do you write in the mornings? Are you writing for the same period of time every day? Is it like two hours? Is it 90 minutes? Is it? Yeah, almost always the morning, although like I'm in the middle of the launch on this new book. And so my routine is a bit exploded. But like my thing is I really don't schedule anything in my calendar regularly.

like we're doing this at 11 central. This is like the first thing in my calendar. And usually I'll do, tend to do a little bit later. I want the mornings free. So probably, you know, from 8.30 to like 11, 11.30 is like,

loosely writing time. So I might be like thinking about the writing that might be reviewing some writing might be going through note cards or it's just uninterrupted, like sitting down writing, but that's the, I make a big distinction between like book writing and,

and other forms of writing that I do. By that, I don't mean like writing emails to people, but like if I'm editing a book for someone or for myself, I can do that later in the day. I can-

write newsletters or blog posts. I can do those kinds of writing, but I feel like book writing demands a level of concentration and focus and frankly, energy that you only have when you are fresh at the beginning of the day. Talk to me a little bit about schedules and how saying yes creates a

it just disrupts your flow, right? So like even this meeting, we got one meeting today. You and I were both talking about this before we came on. It's like, it's the only thing we have today that's sort of booked, but you wake up and you think about it and there's this like hidden tax to it.

Yeah, well, I mean, my whole day is centered now around this because like, so when I look at my calendar, like some people are sort of very scheduled. For me, if the calendar is empty, then I'm spending that time writing, reading, thinking about like my creative work. That doesn't get scheduled. That's the default. So if there's something in the calendar, then suddenly everything else I'm doing pivots around the existence of this thing.

It really highlights to me the cost of saying yes to stuff because it's very clear to me that like, oh, because I said yes to this thing, instead of thinking I've got all day to focus on this in three and a half hours, I have a 15 minute catch up call with some person that I could really be accomplished in the email.

So I really try not to say yes to stuff. And I think it was helpful for me. Somebody told me, you know, everything you say yes to is saying no to something else. I have this performance coach, Jonathan Fader. He's a doctor, but he's worked with a bunch of authors and he worked with...

the New York Giants and the New York Mets, among others. But anyways, I was talking to him about this a couple years ago, and he sent me this picture. And it's a picture of Oliver Sacks in his office. And he's on this old landline phone. But behind Oliver Sacks, he has this giant sign that just says N-O in capital letters, exclamation point, as a reminder to say no to stuff.

He gave that to me as a reminder of the importance of saying no. And his analogy, which I think I talk about in Stillness is the Key. He was talking about like for a baseball player, you're really defined by the pitches that you don't swing at. So I just try to remember that like I have to say no the vast majority of the time.

And it creates this weird, like all of your success in terms of selling millions of books creates this weird sort of paradox where it's almost like the seeds of success plant the seeds of destruction, right? Because all the more obligations come in, more, more questions, you get more inbound. You have to learn to say no more and more. Otherwise it's going to prevent you from doing the very thing that made you successful in the first place. Yeah.

Yeah, yeah. The irony of success is that there are infinitely more distractions from that success. And as you get more successful, the higher the price or bribe

attached to those things is. Right. So early on, it was like, hey, do you want to do a lot of this free stuff? And it was like, well, no. And then now it's like, do you want to say no to insert large amount of money to not do this thing? And and you that's that's really tough. Like, because you think about it, it's like, let's say you get an offer to give a speech.

The amount that you're being offered to do the thing, consult on the project, give a speech, whatever, right? That is a tangible amount of money. As soon as the offer comes in, that money is real to me. So it's not that I'm not earning what I didn't think

about two seconds ago. It's now it feels like I'm taking that money and lighting it on fire. Even though I never had it, I'm costing myself that. Even though again- Yeah, it's loss aversion, right? You feel like it's yours. Totally. Even though three seconds ago, you weren't like, I need this. I'm

hoping that it comes in. What I try to think about now is a more difficult thing to demonstrate, which is opportunity costs. So I also got paid a certain amount to do the book that I'm working on. And if that book is successful, I will earn more because of that. To say nothing of legacy, what I actually care about, what's important, et cetera. So I try to go, okay, but what is one hour of dedicated work

on the book or one dedicated hour on this or that or a day if the thing takes longer, right? I also accepted money to do that thing. And I'm sort of robbing from Peter to pay Paul, so to speak. So I think we're really bad at comprehending, especially in the moment, opportunity costs, but they are always there. And everything you say yes to means you are saying no to something else because you can't do everything. There's always an opportunity cost to everything you do as well as transaction costs.

Right. And I think we struggle with that. And one of the opportunity costs that we don't really see is when we say yes and we do a half ass job like that creates its own sort of problems down the line. Well, of course. Yeah. So let's say I'm continually saying yes to a bunch of stuff.

On the first book, there's a 5% decrease in quality. And then the next book, there's a 10% decrease in quality. The next one, there's a 15%. Now I've significantly fallen off. It was imperceptible to me at the time, but the audience is feeling it. The market is feeling it. The editor is feeling it. And soon enough, you won't get the opportunity to do that anymore. And I think we're really bad at calculating that.

You mentioned legacy. What do you want your legacy to be and how do you measure success for you? I don't think that much about legacy. I guess I just mean at the end of the day, what has more impact, a talk to 15 people at a hedge fund or making the book 5% better or something? I guess I was just meaning more like where is the best return on your investment as far as time? I

I go back and forth to sort of not caring about it at all. And then having some sort of like wanting to be the best at what I do, not so much in relation to other people, but just like I want to be great at what I do.

I do think about legacy in terms of like, am I fulfilling my potential? That's interesting to me, as opposed to like, where do I rank against other people? Because one, I think it matters what timeline you're measuring these things on. And then also, one of the interesting things about writing is that everyone's kind of playing a different game, right?

Right. Like I write about an obscure school of ancient philosophy for the most part. It would not just be torturous, but like unfair to compare myself to somebody writing a book that sells a lot more copies, but about a much easier, more accessible topic.

They're just totally different races and they require different strategies. If you're like, well, you know, this sprinter finished much faster than you. And you're like, yeah, but I ran 400 meters. I mean, they're like, of course, like they did a fourth of the distance that I did. So you've got to figure out like who your peers are and you may not have any.

Well, I think it's also like going to an internal scorecard, right? So I think you sort of hit on the way that I think about this, which is relative to your potential and what you're capable of. Are you getting better than you were yesterday? Are you constantly improving? Are you delivering on that potential? Because everybody starts with this sort of like different trajectory and yours might be higher than mine. But what I really want to what I care about as an adult, as a person is sort of like, how do I maximize what I'm capable of?

within this environment, within these constraints. No, that's totally right. Yeah, we're not... It's not like basketball. We're all playing the same game with the... It's an infinite game versus a finite game or something, right? Like it's just...

Anything that's possible, any way of doing it is possible. And so much of it is outside of your control in terms of like, is it at the right moment? Are you ahead of your time? Are you behind your time? So to judge your success comparative to other people in this profession is just a recipe for complete misery. I wrote this book several years ago about Peter Thiel called Conspiracy, which was like my first stab at what you would call

Actually, first and only so far, stab at what you would call narrative nonfiction. It was an interesting experience in that, one, I think it's one of the best things that I've done. It was certainly the hardest thing that I've done in that it was way outside my comfort zone and my style and not like any of my other books.

But I had this really weird experience with it where it sold probably the fewest copies of any of my books. It wasn't a failure. Just if you're ranking the books, it's like near the bottom. But it got the most critical success.

And then also like split my audience, right? Like some of the people were like, it's your best book. And then some of the people were like, I don't even care about this. I'm not going to read it. Point being, it really helped me decouple all of those things from each other and realize that they're not particularly related.

You can write your best book and it could sell the fewest amount of copies. You could get the most critical reception and it could sell the fewest amount of copies. All you should really focus on is like, are you proud of it? Did you do what you set out to do with it? Now, obviously, if it had sold zero copies...

and been torn apart as wildly inaccurate, or if I'd embarrassed myself in the sense that I failed at what I was trying to do as well. I'm not saying that all success is relative, but it was helpful to me to realize that a lot of these variables that we kind of put in one bucket up here are actually sort of located more on a scatterplot

And you've got to pick which one really matters to you. Let's talk about what you've been writing about ever since I've met you. I think we've known each other, what, seven, eight years now? So let's talk about Stoicism a little bit. What is Stoicism? It's a philosophy that originates in ancient Athens, makes its way to Rome over the next several centuries, and becomes...

I think the most interesting and practical of the ancient philosophies, like when I'm sure when people hear ancient philosophy, they go, that's really interesting intellectually, but a very little use to me as insert, whatever it is that you do. What I love about Stoicism, what gets me excited about it is that all of the Stoics were very

like active elite professionals at whatever they did. And stoicism was a guiding force, a thing that allowed them to do that and guided the decisions they made inside that field. But it wasn't, you know, they weren't Diogenes the Cynic or a Buddhist monk or anyone whose pursuit of a philosophy or a set of ideas took them away from the world.

To me, what I love about Stoicism is that it's very much philosophy for the world. I mean, it's literally founded, one, by a merchant who loses everything in a shipwreck. And two, it's founded in the Athenian Agora, like in the center of Athens, in the marketplace where it's battling for, like from day one, limited attention from busy people who have actual lives.

What are the key sort of like teachings of stoicism that everybody should know? So Epictetus, who's a slave, becomes a philosopher. He says like the primary, the first task of stoicism, he says, is this exercise called the dichotomy of control. It's the distinction between what's up to us and what's not up to us.

Any energy spent on stuff not up to us is wasted and that what we primarily control are our thoughts, our opinions, our actions, our beliefs. So I think the next thing that the Stokes build on top of this idea of the dichotomy of control is we don't control what happens, but we control how we respond. And then Marcus Aurelius building on that says, look, uh,

The everything that happens is an opportunity to practice virtue. So my first book, The Obstacle is the Way, is about this specific stoic teaching that stuff happens, stuff that's out of our control or, you know, we make a mistake with something that's in our control.

And then what we do with that is an opportunity to practice excellence in some form or another. So I feel like the stoic is sort of embracing both their powerfulness and their powerlessness at the same time and sort of fusing it together into this real understanding of where we have agency, where we don't, and what are we going to do with that agency?

Speaking of stoicism, Seneca sort of like said that he had this line, which is like, I shall never be ashamed of citing a bad author if the line is good. I love that. Yes. Which is like a way to learn from you can learn something from everybody. It doesn't make them a good or bad person. There's no judgment implied. But, you know, maybe they had this moment that is like, oh, I can use that as in my repository. Yeah.

my mind, my mental repository of things that I could do. And it could be a good or bad person, but it seems like society today just sort of like wants to chuck out people because they have this blemish. What do you think of that? I think that's totally right. I mean, there's lots of good lessons that come from bad people.

And they're not always cautionary tales, right? Like a lot of people are sort of tragically gifted and flawed at the same time. I think this is a thing that people struggle with. Like history is uncomfortable and it is inherently built around not just like human beings, which are flawed, but usually historical characters, as I was saying, are by definition, you know,

more ambitious, more everything, or like they would have been an unremarkable, forgettable part of history, right? So like Churchill, who I'm fascinated with and write about quite a bit, Churchill's virtues are incredible, right?

But they correspond with equally enlarged vices. And that's what made him Churchill. Just like, you know, you look at, I don't know, someone in the contemporary world like Elon Musk. Elon Musk wouldn't be Elon Musk if, you know, he wasn't all these good things.

But he'd also be considerably less well-known. He'd be like one of the forgettable billionaires on the Forbes list if he didn't also have these corresponding habits. Right. And so I am very much of the school that we can learn from anyone. We can cite bad authors. I mean, the proof of what Seneca is talking about, I'm always surprised.

this has always influenced me from my earliest days of reading Seneca is like in Seneca's letters and his book, Letters of a Stoic is one of the incredible sort of works of ancient literature. The philosopher that he quotes most as a Stoic is Epicurus, right? He's not just saying like, hey, I'll occasionally cite someone I disagree with. The primary source of the philosophy that he talks about in this book

is someone he is vehemently in disagreement with on almost all issues. And in some cases he's quoting where he agrees with Epicurus and in other cases he's saying where he disagrees with Epicurus. But what I think the lesson there is he is intimately familiar with the works

Of all the schools, including the ones he disagrees with. Well, it sort of goes back to that sort of concept of like, if you're going to have an opinion, you have to be able to argue the other side of it better than the other person can argue it right. You have to you have to be able to walk around the problem in this three dimensional way, which means you have to understand other people's perspective into that.

Yeah, I think you've talked about it. But the first person I heard it from was actually Peter Thiel when I was writing Conspiracy. But he talked about steel man, like the instead of, you know, reducing your opponent's argument to a straw man, this sort of caricature, the least, you know,

charitable interpretation of what they think and why, you know, actually really put yourself in their shoes, try to argue it as well as possible. Usually, not only will you find that there's some validity to what they're saying, but it will make your argument stronger because you will have preemptively addressed the

the strongest parts of their argument. So I think people are often afraid to do that. And that's why they sort of understand intuitively there is some validity to what the other people are saying. And their fear of it makes them, you know, unwilling to wrestle with that. So they reduce it to this like,

preposterous caricature. Let's go back to one thing that we had sort of said about people and sort of being, having equal strengths and vices. I think there's an, we talked about this, I think a long time ago at dinner one night, which was, we couldn't, at the time, we couldn't think of any examples of anybody who was extraordinary and well-balanced.

Right. Everybody had this corresponding sort of like offset, like, you know, Tiger Woods and his vices and like anybody who achieved this far right tail success was not anybody that you would hold up and be like, they live a balanced, healthy sort of lifestyle. Yeah, it's like who what what American president would you actually want to be?

Right. Like, like not like, Oh, they've done cool things, but like you have to like live inside their head. And I think this is true for, for billionaires. This is true for professional athletes. It's often like some sort of hole or some sort of wound is partly what drives a person into the public sphere to begin with. And it's also, I think it's, it's why it can be adaptive early on is like, okay,

Okay, look, if Elon Musk was balanced, he probably would have been happy and satisfied with PayPal, right? Like he made tens of millions of dollars. He changed not just the technological landscape, but he changed how money changes hands between people. That's enough, right? Like that ended up, if I was just like, oh, meet this guy, Elon. He's the founder of PayPal. You've heard of PayPal, right? You'd be like, wow, that's so cool.

But he's like not remotely satisfied with that. Right. And then if Michael Jordan was easily satisfied, you know, his high school career would have been enough and then his college career would have been enough. And then the first championship would have been enough. So inherently, the insatiability is the key differentiator in a lot of high performers.

And I think there's a Stefan Zweig quote where he says, never before has a conqueror been surfeited by conquest, meaning no conqueror was ever like, I won and now I'm good. That's enough. Yeah, yeah. Yeah. There never is enough. That's what made them who they were. So I think that's part of it. But as I've worked on this in my own life and had a bit more experience, I do find that like

There's a survivorship bias that we don't think about. So, you know, you think about Michael Jordan, you think about Kanye West, you think about Elon Musk, think about Winston Churchill or whatever. One, because historically the moment may be aligned for that person and that will never happen again. Or they not only were really talented and driven and ambitious, they also had some insatiable desire for success.

public adulation or attention. But like, there's a lot of people who won two championships with Michael Jordan that we don't think about. And so I think we often forget that the people we've heard of more often than not, not only wanted us to hear of them, they needed us to hear of them. And the slightly more balanced people, like...

I don't know. Tom Hanks, one of the greatest actors of all time. He doesn't seem as tortured as Daniel Day-Lewis, you know, and it may be that, you know, because he's not as tortured, he doesn't get covered for being tortured and sort of slides under the radar a little bit.

Yeah. I think there's, there's a couple of different themes to pull out of this. One is like, we see parts of people's lives. We don't see their whole life and it gets magnified by social media. And then we, we feel like, Oh, I want that attribute. And I think it was Naval who said something along the lines of like, never feel jealous of anybody else, unless you're willing to trade your entire life for their life. And you're just seeing this one little sliver of their life. So make sure you see all these other things that go on. Sure. Sort of the,

The other theme there is like, what goes into sort of a balanced, healthy life? Like, what are we going to think when we're 90 about the life that we lived?

Like I used to work with this guy who ended up retiring and, you know, before he retired, everybody wanted to play golf with him. Everybody wanted to talk to him. The minute he retired, nobody wanted to talk to him at all. He's just dead to everybody. Right. And the reason is like he was the boss. So everybody, everybody's sort of like, you can help me do something. And while you're the boss, I'm going to do that. But then he sort of came to this realization a few years later that like the way that he became the boss was,

Was mutually exclusive from sort of like developing sustainable, long lasting relationships with people. And so it was only too late that he recognized this. And I wonder if there's part of us that are like, it's too, you know, we're going to be 80 and be like, man, I wish I would have worked out more. I wish I would have ate healthier. I wish I would have spent more time with my kids. I wish I would have, you know,

not done this, some of this stuff that I'm doing now, or I wish I would have taken all my relationships and just thought of them as like, you know, this, this person is going to be in my life for 30 years and that'll change how I act. Right. Like you and I have been friends for, I don't know, eight years now. And like, I know you're going to be in my life in 12 years and that changes our relationship in a way, right? Like it sort of nudges, it pulls us towards better behavior.

Yeah, there was a interview I read. Is it Michael Chabon or but anyways, the novelist. And he was saying that early on in his career, before he had kids, some sort of grizzled old novelist, like, I don't know, a Hemingway type said something like, you know, every kid you have is a novel you won't write.

And that really hit him. And then he ended up having kids anyway. And in retrospect, he's like, I would take that trade like every day. Right. And so I think one of the things that you realize is that the professional first off, the professional success is not nearly as unprecedented or special as you think it is. It's more ephemeral than you think it is. But like when you really think about

the things that it often comes at the expense of, it's only in retrospect that you're like, oh, that was a bad trade. And so for me, like when I, sometimes people will ask me what my goals are and I've always like, so my three goals are I want to be a great writer. I want to have a great marriage and then I want to be a great father. And so those three goals have to be

In constant relationality to each other, because certainly you can be better at one at the expense of the other. But they really only matter if they are done in concert with each other.

And, you know, if you told me that, hey, I was a great father, but like I gave up all my potential as a writer. Now, look, if I had no choice, of course, I would accept that. But there would be regret and pain in that. Right. Because I would have felt like I was rejecting a gift that I had. Now, if you told me if you could like actually show me like Ryan and.

your books would be 25% better. You'd be more famous. You'd have made more money, but you have to undo the kids that you have. Like you, like your kids cost you that I'd be like, okay, cool. Instead of having like really concrete career goals, I think more about sustainability. Like I want to do it over a long period of time and I want to do it not at the expense of these other two things that are important to me.

I think that what you're really getting at is sort of like the harmony between those things, right? Like it's not a balance. It doesn't imply like giving and taking, but it's like this constant sort of repositioning based on what the needs are at the time and sort of like not necessarily sacrificing everything else. But, you know, the kids are in school, so you can work, right? But when the kids aren't in school, maybe it's like, oh, I'm going to work less because I want to be with them. And sort of I think that when you start thinking about life that way, it sort of changes how you think.

Yeah. And I think about it in terms of like, well, what do I need then to do all these things? So like, let's say I'm younger. I can sort of white knuckle it. I don't have to have the same level of habits. I can be more inconsistent. Maybe I don't have to invest or spend to like set up like that.

But as I've had kids, it's like, oh, okay, like if I want to keep doing it, now I do. It's like an athlete getting older has to spend more time doing recovery work because like their body can't handle it. And I think like as you take on other responsibilities, your priorities in your life,

you have to figure out how to adjust for that to continue to perform at an elite level. And you almost certainly can't just do it on raw willpower or talent alone anymore. It requires a team. It requires an environment. It requires a

routine, you know, it requires all those things. So I feel like I've, as I've had kids and then in pursuit of this balance, I've had to professionalize more. And even like in my marriage, it's like, oh, like I can't just be consumed with what I'm working on all the time. Work can't be the default mode. It has to be like, when I'm at work, I'm at work. You know, I, you have to, you have to professionalize and systematize, uh,

if you want to sustain it over a period of time. I was actually reading the new biography about the New England Patriots, the "It's Better to be Feared." It's like an incredible book. And actually one of the things that I never thought about it this way,

I sort of saw Tom Brady leaving the Patriots as part of his insatiable desire to win, to be in control. Same as Kevin Durant leaving the Warriors to go to the Nets. But reading this book, it was it actually Seth, the author, explains that he he views it more in the light of Tom Brady's wife and kids being like,

You have to be a regular person. It was basically like the New England system was not sustainable for a 43-year-old multi-champion. This isn't sustainable from a work-life balance perspective. And also, what good is all your success if it still makes you unhappy and unable to

as a well-adjusted person in your life. And so part of, he, he sort of phrases as part of the transition was like, yes, I want to keep winning, but I also just actually love playing football. And I want to go play football the last couple of years, somewhere where it's fun and it's integrated into my life in a way that doesn't make me, uh, a miserable wreck all the time. Uh,

and I don't think this is so much an indictment of the Patriot system so much as like, there's a time and season for different phases of an athlete's development. And like, again, being a 22 year old NFL quarterback, uh,

who's not won anything is very different than all the championships that he'd won. And he's now 43. And the other, the other point that you mentioned a while ago was sort of longevity, which I think is often something where we have to pay a cost today to get longevity, but we don't want to pay that cost. An example is sort of like eating healthy might be difficult for you. It's not for you personally, but like,

uh, exercising, right? So exercising might be an hour a day cost, but it's going to improve the odds that you can do what you do longer. And if you look at the best sort of like professional athletes, their entire life, like Tom Brady's life is organized around playing football as long as he possibly can. Right. And whatever support staff that needs from like a

personal chef to sort of his personal trainer and all of this being involved in his life. Like he looks at that as like, this is enabling me to do what I do. I need to work out every day. I need to stretch. I need to get a massage. I need my life organized in a way that's maximizing that. And he's also looking at it from longevity, right? So there's a daily cost to this stuff where you might be able to maximize your sort of like

immediate value by writing twice as fast, burning yourself out, you know, killing your marriage, not seeing your kids and you get these immediate rewards. And we often sort of like, I feel like we have this conversation with ourselves and we say, oh, I'm going to do it until I reach this point. And then I'm going to quit. Right. Like, I'm just going to do it for this book. But like, as you said, that appetite is sort of never fulfilled and you can never walk away. And then you sort of end up burning out and flaming out, which limits your, you know, where you're

reach your potential and limits what you're capable of doing. I worked on this book. I know you had him on the pockets with Chris Bosch. And one of the things I was asking him about for letters of a young athlete, because I'd heard that LeBron James, you know, spend something like a million and a half years,

dollars a year on his body, like trainers, massages, medical treatments, et cetera. And he was like, oh yeah, it was crazy. You know, the rest of us were like, we're young. We don't care. We want to, we want to play video games on the plane. And he's like doing yoga or he's taking ice. He was, he was always doing, and here he is still playing. And the rest of the big three is not in the league anymore. A certain amount of that is luck. Like

Obviously, you know, Tom Brady has the benefit of not getting hit to the degree that other quarterbacks have or no real catastrophic injuries. But the investment in the body and sustainability is like really huge. I've got to imagine like if you're Steph Curry, having a father who is a professional athlete.

helps you understand this is like you you come from a lineage of people who've done this before. Most of the time, though, you're a first generation at whatever you do, especially at like the elite level. So it's it's hard to like really pick up these sort of pro habits.

whether it's investing or hiring or scaling or shortcuts or, you know, taking care of yourself. But like you have to figure these things out because like the real cost is not money. It's in how many years of being able to do this. It cumulatively deprives you of.

Let's switch gears a little bit because I want to get into some more meaty questions here. What do you know about making decisions that most people miss? I do tend to find we often spend too much time thinking about the decision instead of just fucking making it.

and dealing with the consequences of it. So I, there's a story I tell about George Marshall where he goes, don't fight the problem, decide the problem. So I tend to find in my thing, like I'm a big believer in momentum and I'm a big believer in crossing things off the list. So sometimes this costs me cause I'll be hastier than I should have been. But like,

What will be frustrating to me, especially if someone I work for, I'd be like, I'll bring something up, be like, hey, you have to decide whether we're doing this or this. Right. And then like three days later, three months later, I'll check in on and they'll be like, oh, I'm still thinking about it. It's like, OK, but you just cost us three months of not having it either way. And whatever the margin of error would be between one decision or the other is overwhelming.

far smaller than whatever the opportunity costs of not having it done and moved on to the next thing are. Totally. Do you want to go a little deeper on that in terms of like momentum and how that works for you and how you think about that in the context of decision making? Well, so as a writer, for instance, I'm all about momentum. So every day, like I told you about how I sort of

work on books, but I break each thing up into smaller pieces. And so I want to have the sense that I'm crossing things off, that I'm making forward progress. Let's say I have a bunch of chapters I have to write for this section. Now, there's one section that I kind of knew what I wanted to do and another section that I could do it this way, I could do it this way. I don't really have the right example. Am I going to do the hard one first or the easier one first?

In this case, I'm going to do the easier one first because stalling out is the main thing that I want to avoid. It's not that I'm going towards the path of least resistance, but I'm going towards what

where I'm going to make forward progress. And so I like to do things in order. For instance, I like to do them according to plan. But if you're telling me that I'm starting to get damned up over here, I'm going to pivot and maybe I will flash forward. And like the book that I'm working on now, which is about self-discipline, I didn't have enough material to write the main chapter for the second part of the book.

But I did know all the subsequent chapters I was going to write in the book. So I started with the subsequent chapters. And then only last week did I circle back to put in the main thing. So instead of stalling out, going like, I can't write until I do all this stuff.

I wanted to have the forward momentum while I was working on the other stuff. So I'm just a big believer in momentum in that sense. Going back to stoicism a little bit, how do we learn to accept the things we can't control? I mean, you don't really have any choice, I guess. Like we have to go, well, I can't accept this. And it's like, well, does not accepting it mean that it didn't happen? So what we're really talking about is like the stoics, um,

They use this word ascent, not like ascent up a mountain, but A-S-S-E-N-T. And it just means like you're acknowledging that it happened. You're like giving it permission to have happened. So when we're talking about, well, I can't accept things that are outside my control. You have accepted them. They have happened. You had no choice. Like no amount of objecting undoes them. What we're really talking about is like whether mentally you're okay acknowledging that they happened or

or that you're at peace with the fact that they happened. And so if we think about it like that, I do think it becomes a little easier. What about like sort of the people that focus continuously on, I'm thinking like the way the world should work versus the way the world does work? Yeah, this is like an important part of stoicism too, because if you have high standards, it's very easy to expect other people to live up to those standards.

And invariably they do not. Right. I think we struggle with acceptance because it feels like you are saying that because it happened, it's like good that it happened or that it should have happened. Right. When really, I think what the Stokes are saying is like accepting that it that it's a fact on the ground.

does not lessen your obligation to prevent it from happening in the future, or it does not mean that it was okay, like it wasn't immoral or unjust that it happened. Saul Alinsky, the activist, says the social organizer has to start with the world as it is for what it is,

if they want to change it. I think the problem with a lot of idealistic people, particularly people who are interested in social change or social justice, is that their preoccupation with how they want things to be puts them at odds with how they are and actually makes it much less likely that you'll be able to do anything with it.

Look, I'm fascinated with ancient philosophy. If you told me I could write books that are much headier and go off into the weeds because everyone was well versed in the basis of philosophy and we could have these really high level discussions about it.

That would be cool with me. I mean, I would probably prefer that. But the reality is most people are not interested in philosophy. And so if I want to speak to them about philosophy, I have to meet them where they are and write and communicate accordingly. It'd be great if everyone spoke this language, but they speak this language. So talking to them in the language of your choice isn't going to communicate what it is that you feel needs to be communicated. It is what it is.

There's this great quote by Joseph Tussman that comes to mind that I've actually never been able to verify, but I've seen a couple of times now, which is like what the pupil must learn if he learns anything at all is that the world will do most of the work for you, provided you cooperate with it by identifying how it works and align with those realities. If you

do not let the world teach us, then it teaches us a lesson. It's sort of like, are you going with the grain or are you going against the grain, right? Can you find a way to make the current work for you as opposed to against you? And I think a lot of times we create headwinds unnecessarily by either being too ambitious. And this also goes to the point of momentum. I think you're seeing this politically in the US right now. Even though Biden has like the thinnest

of legislative majorities

like the progressives in the Democratic Party are trying to pass this like pretty aggressive, like transformative social change. And as a result, they're accomplishing like nothing. They're pushing their advantage too hard. Yeah. And to the point of not having an advantage, like whereas it had they started small and racked up a number of legislative gains, they would not only have

momentum, but would probably be in a stronger position coming up to the midterm elections. And I think Robert Caro does a pretty amazing job of this, studying the transformation of Lyndon Johnson, particularly as it pertains to civil rights. You know, Johnson passes the first civil rights bill in like 100 years that's mostly symbolic, that does next to nothing. Basically, the only, I think, part of it that had any teeth was that

It took civil rights cases out of juries, which was sort of a stymie point that the South would use because they could just use jury nullification to protect any any governmental abuses of like voting rights and stuff like this.

So he's sort of he's like, well, what's like the key issue here? Like, what is the the main impediment to even the slightest bit of momentum? Let's just focus on that. So it looked like a relatively toothless legislative package.

But it actually had this one key part in it that sets up the next civil rights adjustments. And and, you know, Kennedy, who's much more idealistic than Johnson, a much better speaker, probably much more committed, frankly, to civil rights, you know, does a lot of great talk.

and has a better idea of how things should go, but in his brief presidency isn't able to make any progress. And so you have to wonder if your unwillingness to accept reality is actually perpetuating the very reality that you seek to change.

Going on to the next sort of topic, how can we learn to manage our anger? I was thinking about this with a course that we made for Daily Stoic. I was saying that like, just because you don't have an anger problem doesn't mean that anger is not a problem for you.

Right. Like when I look at most of the mistakes that I made, most of the things that I regret, most of the things that I wish I could undo, usually anger is a pretty big part of that.

Right. Like anger was a driving factor in why I wrote the email and sent it. Right. It was why I chose not to do X, Y or Z. You know, it's why I was speaking this way or that way. So I think, you know, the question about anger is like, does it actually make you better at what you do? It may in the short term. Right. And to go to our point earlier about sustainability is.

Is it fuel that can get you where you want to go over the long term? Or is it really corrosive? And usually I tend to find that it's pretty corrosive fuel. So I think if we just start with like,

let me make sure I'm not lying to myself about my temper, right? Because a lot of us tell ourselves like, oh, it's because I really care or it's what drives me. I'm not as bad as my boss or my dad or whatever. But like, if you really step back and you said like, what is this actually adding and what are the costs that it's coming at? It usually becomes pretty illustrative that it's not a positive force in our lives.

What are the other sources of mistakes when you find yourself making mistakes? Are there other sort of like common themes to those that you can pull out? Well, the Stoics talk about the passions, right? And, you know, today, obviously, we talk about passion being a good thing. But I would say at the root of most mistakes, both personally and sort of historically, it's one of the passions, right? Envy, lust, anger, fear, you know, pain, worry.

worry, you know, those sort of

emotional states that take us out of the rational part of ourselves and into some sort of frenzied or flurried or consumed part. You know what I mean? Yeah. The way that I think about that is they sort of like, they nudge us against reason, right? So they make us more instinctive and less reasoning at the same time. And those are the very moments that humans, unlike any other sort of

mammal can, you know, like any other animal can actually like, no, I'm going to put a two second pause on this. And I'm going to think before I instinctively respond, because those instincts might have served me really well in the Savannah, but they're not necessarily going to serve me well here because I'm about to do something that can't be unsaid or can't be undone. Or I remember reading about this in Lives of the Stoic, which I have right here about the, well, I think it was the emperor who stabbed the guy with his

pan in the eye, right? In a fit of rage. And then he couldn't undo it. Yes. No, and it's often precisely the situations in which we are overcome by passion, we have the slimmest margin for error. It's like, I've talked to people about this, about anger specifically, let's say like politically, especially right now.

It's no question like what's happening in the world is is appalling and frustrating and in some cases like downright evil. So you have to ask yourself, OK, like so you're looking at this person who's in the way of what you see as progress. So either.

Let's say it's an individual person. We're talking about vaccines or masks or it's some politician who's stymieing some important bit of legislation. Either they mean well and are massively misinformed. Right. In which case, anger, let's say, is not going to convince them. Yeah. Or they are pathologically evil. Right.

in which case you can't afford to be angry because they're not angry, right? Like they're pathologically evil or a narcissist or toxic or whatever. And so the idea that you can afford not to be hyper rational and strategic and in control of all of your faculties, you're in really bad shape. I think you could argue that

What Trump does, and I don't think this has to get political, what Trump does is, I don't think it's so much a function of genius on his part, so much as a confluence of personality traits, so enrages his opponents and disorients them and is so the opposite of what they have experience dealing with.

that it's almost like a self-protective bubble, right? Because it's like he's inside the loop of the opponent. And because they're not thinking rationally, patiently, strategically, they're just like, ah! Yeah, he's hacked your operating system, right? Like he's literally just hacked your brain and he's making you respond in a way that's advantageous to him and disadvantageous to you. How do we overcome that? Like how in the moment,

Do you like is there any stoic advice or anything that you've learned where it's like, do you take I think there's one quote about sort of like reciting the alphabet before you respond. Yeah, there's all these practical tips that we've learned as adults, like don't send the email, leave it as a draft, read it again in the morning. Well, it's funny, one of the advisors to the Emperor Octavian is this stoic Athena Doris.

And he actually says this. He's like, look, as the emperor, you will be provoked. You will be angry. He's like, but I want you to recite the letter of every letter of the alphabet before you do anything. And I love that that's like 2000 year old piece of advice that you would also give your seven year old. And yet the most powerful man in the world needs it, too. The idea of the pause, I think, is super important in all things. Right. Because like very rarely are are.

Is that immediate solution the right one? I think we talked about Kennedy earlier. Think about the Cuban Missile Crisis. You know, he was able to string out a nuclear standoff over 13 days, but it was only by stretching it out, by using the time, by talking about it, by talking through it, that

that he allows not just his own advisors to sort of see things in a better light, but he allows his opponent to come to their senses too. And I don't think that would have been possible compressed into three days. George Washington, one of his favorite expressions, it actually comes from a line about the Stoic Cato. He says, I want to look at everything in the calm light of mild philosophies.

And I think that's being rational. That's being empathetic. That's being not frantic or rushed. And I think it's important to point out, like people who knew George Washington were like, he has a horrible temper. You know, he is an impulsive, deeply passionate human being.

But it's that he got control of those things because his positions demanded it. So this isn't a like, oh, I just have a good temperament kind of thing. It's like you have to cultivate that temperament.

Particularly if you're in some position of leadership or responsibility. And you can't practice it in the moment where it's the most difficult, right? Like you have to practice it in these little, somebody slights you, you know, almost on the playground, you're like, whatever. Like these are the moments where you practice your response because when it's large, when you're on the stage, when the lights are on and when everybody's watching you, that's not when you want to practice.

You want to have that instinctive response. It's like if you haven't practiced it in the little areas, it's very unlikely you're going to be able to do it. Like when the game is on the line or your career is on the line or like the eyes of the world are upon you. Totally. Okay. I want to come to lives of the Stoics for a second. One thing that I learned reading this book that I had no idea about, and I think most people actually have no idea about is like, what made Cicero so shady, man? Yeah.

I think it's ambition. I don't know if I, shady is not the right word, but he, it's kind of the right word, but I think what he was, was your sort of consummate politician who loved politics more than policy or principle. He just never seems to understand that doing the right thing is

is ultimately more likely to ensure you the greatness or the success that you're after than doing the expedient sort of self-preserving thing. So he's just always thinking about the next office. He's always thinking about the next opportunity. He's always thinking about what's going to help him.

And the result is he basically betrays everyone, gets a reputation for being precisely that. And, you know, when it counts is both failed by and fails Rome. The way that I read that in both books or lives of the stoic and sort of courage is calling is that like he never really commits to anything.

Yeah. He's always sort of like channel surfing for the opportunistic angle to whatever. So he's sort of like so flexible, but like, if you think of all the people that we tend to admire in life, they're committed to something like whether it's sort of like building a company, whether it's character or virtue, but that,

they don't waver. They're just a hundred percent committed to that. And so often, like not only like a lot of us are like Cicero, like we're channel surfing, we're looking for that thing and we're not committing to anything. What's your response? Like, how do you respond to that? There's this great moment where after Caesar comes to power and Cicero had up until this point been this like lover of the Republic. And then he just sort of rolls over and lets Caesar do what he does, but he'd sort of kept one foot in both camps.

And this guy gives this speech where he sort of criticizes Caesar to his face. You know, Cicero congratulates the guy after he says, come over here and sit with us, sit next to me. And the guy, he's like, I'm surprised there's a chair next to you because you sit on two stools, meaning that he always does precisely that. He tries to play both sides. Basically, Rome has two civil wars in his lifetime. And he goes, I'm just going to wait.

pick the, when the winner reveals themselves, that's who I'm going to side with. Well, so he barely survives the first civil war. He's always regarded as with suspicion. And then the second civil war happens and,

And then, you know, eventually it shakes itself out and Cicero gets killed anyway because they saw like it was so preposterously transparent. This idea that you can play it both ways. It never works. Right. Eventually the music stops.

And they see you for what you are. One of the things a lot of the Stoics have in common, at least like Marcus Aurelius and a lot of maybe not Stoics, but more prominent people in life is that they journal. Yes. What we're talking about is a lot of like sort of self-awareness and self-criticism, right? The sort of evaluation of how one is doing and how one could do better.

And I think journaling is pretty much the most effective way we've found to do that. I mean, I think it's a little bit there in meditation, but I mean, part of meditation is not thinking. Right. And so I think journaling is just as I have experienced it and I understand it. Journaling is the conversation we have with ourself about who we want to be and how far we are from that at any given moment.

And I think that's necessary in from a reflection point of view, because I think one of the keys to learning and improving is not just sort of having this experience. It's actually your reflection on this experience is what's going to cause you to create an abstraction. And the abstraction is going to be your action. So if you think of learning as a loop, right, you have an experience. It could be yours. It could be this conversation that you're listening to. It can be a book that you're reading. It can be somebody at work.

But the real key to that learning becomes the reflection. Like, what were the variables that mattered? How do I digest this? How do I process this? How do I distill it? And so often what we do in day-to-day life is we consume other people's abstractions without the reflections.

And so we have this illusion of knowledge. So when we're journaling, what we're doing is we're teasing out that illusion of knowledge, but we're also taking our experiences and we're translating them actively into sort of abstractions that we can use that become actions that we can take. Well, look, I think it's also the codification of what we've learned. So like for a sports analogy, if just like instruction and then experience was enough,

Why would players ever watch game film? Right. Like they were there when it happened. Obviously, they know what happened, but it's not true. Right. You break it down. You need to look at it minutely. You need to evaluate yourself not in the moment, but from a distance. And I think it's in the pages of a journal that we have the ability to go through.

well, here's what you want to be, but here's who you were today. You knew today was a travel day and you thought about not being anxious, you know, being patient, going with the flow.

And here we are the next day or that evening and you're like, but you had a meltdown, didn't you? Right? Why did that happen? What triggered you? What could you do differently next time? How do you think other people saw this? Right? And so that sort of ability to reflect and analyze and discuss is really important. And I think the other part is it's not just our behavior. There's an Anne Frank line I love where she says, paper is more patient than people.

It's also like the things that I've thought or believed or been frustrated with people about that I've kept, like by writing them down in the journal, I felt like all the ferocity of that feeling went away. And so instead of vomiting that all over someone, you know, because they left the toothpaste cap out, you processed it and then you were just like,

hey, I feel like we're not in sync. What's going on? Right. Instead of like, what the fuck is this? You know, like, so, so you're able to, you're able to, to, to get it out in a safe place. It also sort of slows you down, right? So in decision-making, we, we advocate sort of an approach when we work with people on improving their decision-making about write the decision down at night that you're

that you're about to make and then read it in the morning and see if it still makes sense to you. And what you're really doing is you're doing a couple of things, right? Like you're processing, whether you comprehend that in a way that you can explain it to yourself, you're checking in with your rational and emotional self. You're taking yourself out of system one. You're putting yourself in system two when you, you,

you go the night and you read it in the morning. Most of the time you're like, oh, that, you know, maybe that doesn't make sense or that wording isn't quite right. And you can sort of self-correct. And I think that it also helps you reflect on the decision in short. What are the variables that matter? How are you thinking about it? And you're getting out of that sort of like

instinctive response and you're putting yourself in a situation where you're improving the odds that you're at least using reasoning. No, and this is true in communication as well. Like the two or three biggest scandals of Truman's presidency are

are basically letters. He was a reasonably controlled and decent person, but when he got upset, he would write and say things that he shouldn't say, that upon reflection, he regretted saying, but he'd already put it in the mail by the time that reflection could have happened. Lincoln, conversely, would write these letters that he would leave in the drawer of his desk, right? And almost never send. And

And so I think about like there's almost never been like a firm or a strict or a negative like email that I've had to send that upon sitting on for 24 hours or sometimes like a week.

that I haven't made some changes to. That's not to say that I don't send it. I almost always do send it. But I just realized that what was talking was less me trying to solve the problem and me venting about the problem. And so, and I'm not even saying it fixed the situation, but like, I think about it, it's like, look, they're still probably gonna be an asshole in response to what I have to say. If they were, if they weren't,

We probably wouldn't be having this conversation. But I know that if someone else were to look at it, if I were to evaluate it against my own conscience, if it were to be public, that I know that I didn't provoke this, that this came from them. And there's no evidence that, you know, no one can go,

Hey, you're both to blame here. Right. Because I took the time to reflect, be in control of myself and not let sort of passion dictate. And then we all also make these mistakes, right? Like you slip up, you mess up and,

I think the point of those is like, okay, well, that's fine. But like, get back on the horse, right? Like, don't just sort of throw everything away, because we are all flawed in various ways. We all will make mistakes. You can't sort of make one mistake and throw it all in the air and wash it away. When Yeah, like, let's say you send the email and it blows up in your face. You're like, okay, I knew better. I did it anyway. Yeah.

I can't undo it, but I cannot do it again. Well, let's sort of switch gears and end with sort of the four stoic virtues. Courage is calling is there. And what are the other ones? What are they? Why do they matter? And how do we use them? So the cardinal virtues in stoicism and Christianity and most of Western philosophy are courage, temperance, which means self-discipline, justice and wisdom. So I am doing a four book series on those courage being courage.

The first, I think, the most, let's say, necessary but not sufficient of the virtues is

And so, you know, we talked about earlier, like Marcus Rios saying that every situation is an opportunity to practice virtue. I think what he means is that there's no situation so good, so bad, planned or unplanned. It does not demand from us one or more of those virtues. So go into more detail, though, like temperament or sort of self-discipline. What is that? What does it mean? What does justice mean?

So I've only written the first book and I'm halfway through the second. So my definitions are going to get wordier as we go on because I've yet to refine them. But my definition of courage is that courage is putting your ass on the line, literally or figuratively. Self-discipline is the standard to which you hold yourself. That's

That to me, that's what moderation is like, not what you can do, but what you allow yourself to do. Right. Not what's legal, but what you what you choose.

Justice. I think justice is a more encompassing virtue than than perhaps the word suggests to me. It's something akin to the golden rule. Right. Like treating people the way that you would like to be treated. You know, honesty, respect, decency, fairness, etc., etc.

It's doing the right thing, right? Whatever that thing happens to be. And then wisdom is not just the pursuit of knowledge and understanding, right?

But particularly the almost intuitive sense of like how much courage is required, how much temperance is required. Right. What is the right thing? So wisdom, the final virtue is the virtue that kind of unlocks when and how to apply the other virtues. And we get that from experience, from study, from mentors and from from life.

Thank you so much for taking the time today, Ryan. I think this is a great place to end this and I really appreciate it, man. I'm looking forward to the next three books. Yeah, I'm excited and I want to know all about the timeline on your book. That's a great place to cut this up. The Knowledge Project is produced by the team at Farnham Street. I'd love to get your advice on how to make this the most valuable podcast you listen to. Email me at shane at fs.blog.

You can learn more about the show and find past episodes at fs.blog slash podcast. To get a transcript of this episode, go to fs.blog slash tribe or check out the show notes. Can you do me a small favor? Go online right now and share this episode with one friend who you think would love it. Thanks for listening and learning with us. Till next time.