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.
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Ryan Holiday is here today.
Ryan is a prolific author and modern philosopher, as 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.
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 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 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 doing it every day, it does seem to me that more published work for people should come out of the other side.
I am amazed. Maybe it's because writing is a creative profession that people don't treat like professional sports or trading or anything, where it's just sort of excused because people think it's hard and they don't understand how it works.
They're just a really tolerant 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.
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.
There's not this sort of existential angst about what I do next.
Again, likening it to sports, they know the season starts at the same time every year and that there's always another year unless you retire.
It's not like, should we get a league together this year?
Should we play this year?
I know I've got the next project.
There's usually a contractual obligation slash deadline for that project.
That keeps me really honest.
I'm also always reading, and so the reading is creating the material, which is then setting up the next book.
I have this system that is just in motion all the time and I'm a part of it.
When do you read? 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?
How regimented is that?
If you'd asked me before COVID, I would have said, I read a lot on airplanes and in hotel rooms.
I wouldn't do anything but read when I was traveling.
That's where I made up a lot of it.
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.
I wouldn't say it was a struggle.
Obviously, early on in the pandemic, I got tons of reading in because there was nothing but time.
I would say lately, I've been trying to figure it out a bit more.
I've been out of a rhythm, which I guess would be another point, which is for me, I am just generally more of a binge reader than I do 200 pages a day or something.
If I'm finding awesome books in a row, I might be banging them out like that.
If I'm like, you pick up a book and you're like, this is okay, and I know I want to read this, but it's a bit of a chore, then that can grind the whole thing.
If you get a couple of those in a row, suddenly you're like, am I good at reading anymore?
A couple big parts of my reading is I read while I eat lunch, I'll read for 45 minutes or an hour.
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.
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? Almost always the morning, although I'm in the middle of the launch on this new book, and so my routine's a bit exploded.
My thing is I really don't schedule anything in my calendar.
We're doing this at 11 central.
This is the first thing in my calendar, and usually, I'll tend to do a little bit later.
I want the mornings free, so probably from 8 .30 to 11 .00, 11 .30 is loosely writing time, so that might be thinking about the writing, that might be reviewing some writing, might be going through no cards, or it's just uninterrupted sitting down writing.
I make a big distinction between book writing and other forms of writing that I do.
By that, I don't mean writing emails to people, but 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 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 it just disrupts your flow.
Even this meeting, we got one meeting today.
You and I were both talking about this before we came on.
It's the only thing we have today that's booked, but you wake up and you think about it, and there's this hidden tax to it.
Yeah, well, my whole day is centered now around this because ...
When I look at my calendar, some people are very scheduled.
For me, if the calendar is empty, then I'm spending that time writing, reading, thinking about my creative work.
That doesn't get scheduled.
That's the default.
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, oh, because I said yes to this thing, instead of thinking I've 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.
I really try not to say yes to stuff.
I think it was helpful for me.
Somebody told me, 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.
He worked with the New York Giants and the New York Mets, among others.
Anyways, I was talking to him about this a couple years ago.
He sent me this picture.
It's a picture of Oliver Sacks in his office.
He's on this old landline phone.
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.
His analogy, which I think I talked about, and still this is the key, he was talking about for a baseball player, you're really defined by the pitches that you don't swing at.
I just try to remember that I have to say no the vast majority of the time.
It creates this weird...
All of your success, in terms of selling millions of books, creates this weird paradox where it's almost like the seeds of success plant the seeds of destruction.
Because more obligations come in, 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, the irony of success is that there are infinitely more distractions from that success.
As you get more successful, the higher the price or bribe attached to those things is.
Early on, it was like, hey, do you want to do a lot of this free stuff?
It was like, well, no.
Now it's like, do you want to say no to insert large amount of money to not do this thing?
That's really tough.
As you think about it, 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.
That is a tangible amount of money.
As soon as the offer comes in, that money is real to me.
It's not that I'm not earning what I didn't think about two seconds ago.
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.
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.
I also got paid a certain amount to do the book that I'm working on.
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.
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?
I also accepted money to do that thing.
I'm robbing from Peter to pay Paul, so to speak.
I think we're really bad at comprehending, especially in the moment, opportunity costs, but they are always there.
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.
I think we struggle with that.
One of the opportunity costs that we don't really see is when we say yes and we do a half -assed job.
That creates its own problems down the line.
Of course, yeah. Let's say I'm continually saying yes to a bunch of stuff.
On the first book, there's a 5 % decrease in quality.
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.
Soon enough, you won't get the opportunity to do that 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 go back and forth to not caring about it at all and then having some 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 am I fulfilling my potential.
That's interesting to me as opposed to where do I rank against other people because one I think it matters what timeline you're measuring these things on and then it also one of the interesting things about writing is that everyone's kind of playing a different game.
I write about an obscure school of ancient philosophy for the most part.
It would not just be torturous but unfair to compare myself to somebody writing a book that sells a lot more copies 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 it's 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?
Is the are you ahead of your time?
Are you behind your time?
So to be 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 non -fiction.
It was an interesting experience and 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 and 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 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 you know if I like embarrassed myself in the sense that I like 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 scatter plot and you've got to pick which one really matters to you.
Let's talk about what you've been writing about for both.
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.
I'm sure when people hear ancient philosophy they go that's really interesting intellectually but a very little used 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 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 the next thing the stoics 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 and speaking of stoicism
Seneca sort 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 that you know that maybe they had this moment that is like oh I can use that as in my
repository 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 more ambitious more more everything or like they would have been an unremarkable forgettable part of history right so so like Churchill who I'm fascinated with and write about quite a bit Churchill's virtues are incredible 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 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 forage 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 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 in disagreement with on almost all issues and in some cases he's quoting uh where he agrees with uh 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 the first person I've I heard it from was actually Peter Thiel when I was writing conspiracy but he talked about steel man like the the instead of you know reducing your opponent's
argument to a straw man this sort of caricature the least uh you know uh charitable interpretation of what they think and why you know actually really put yourself in their shoes try to argue it as 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 uh the strongest parts of their argument so I think people are often afraid to do that and that's why they 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 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 uh you know tiger woods and his vices and like anybody who achieved this uh far right tail success was not anybody
that you would hold up and be like I 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 you 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 look um if Elon Musk was balanced um 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 um that's enough right like that in and of its 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 um 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 like never before has a conqueror been surfitted by conquest meaning like no conqueror was ever like I won and now I'm good right like 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 um 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 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 um and it may be that um 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 gonna think when we're 90
about the life that we lived like I used to work with this guy who 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 gonna 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 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 gonna 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 the 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 it pulls us towards better behavior yeah there was a uh interview I read is it Michael Chabon or but anyways the the novelist and he was saying
that early on in his career um before he had kids uh some like sort of grizzled old uh novelists like I don't know a Hemingway type uh 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 uh I think one of the things uh that you realize is that the professional first off the professional success is not nearly as unprecedented or special as you think it is um 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 ask me what my goals are and I've always like sort of my three goals are um 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 um because certainly you can be better at one at the expense of the other um but they really only matter if they are done in concert with each other and you know if 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 if I had no choice of course I would accept that but I there would be regret and pain in that right because I would have felt like I was rejecting a gift that I have now if you told me if you could like actually show me like Ryan your books
would be 25 percent 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 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 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 gonna work less because I want to be with them and sort of I I think that when you
start thinking about life that way it sort of changes how you view things yeah and and I think about it um 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
um maybe I don't have to invest or spend to like set up like but as I 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 uh 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 how to adjust for that to continue to perform at an elite level it and you 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 um 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 Tom Brady leaving the patriots as part of his insatiable desire to win to be in control same as Kevin Durant leaving uh the warriors to go to the the nets but reading this book it was it actually uh Seth the author uh 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 like he it was basically like the new england system was not sustainable for a 43 year old you know yeah this isn't sustainable like from a work life balance perspective and also like what good is all your success if it still makes
you unhappy and unable to function as a well -adjusted person in your life and so part 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 years somewhere where it's fun and it's
integrated into my life in a way that doesn't make me a miserable wreck all the time 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 who has 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 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 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 gonna do it until I reach this point and then I'm gonna quit right like I'm just gonna 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 reach your potential limits what you're capable of doing I I worked on this book I know you had them on the pockets with Chris Bosh
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 spent something like a million and a half dollars a year on his body like trainers massages medical treatments etc 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 you know 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 uh to the degree that other quarterbacks have or no real catastrophic injuries but the investment uh in the body and sustainability is 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 uh 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 uh 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 because I'll be hasty than I should have been but like what will be frustrating to me especially with someone I work for I'd be like
I'll bring something up to be like hey you know 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 it and they'll be like oh I'm still thinking about it's like okay 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 far smaller than whatever the opportunity costs of not having it done and moved on to the next thing are totally do you do you want to go a little deeper on that in terms of like momentum and how that works for you and 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'm 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 um I have a 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 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 gonna 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 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 why 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 assent 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 they're 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 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 uh 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 stoics 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 uh that that it was okay like that it was it was it wasn't immoral or unjust that it happened Saul Alinsky the the activist says like uh you know 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 like look I'm fascinated with ancient philosophy if you told me I could write uh 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 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 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 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 to her yeah and and to the to the 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 the transformation of Lyndon Johnson particularly as it pertains to civil rights you know Johnson passes the first civil rights bill in like a hundred 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 uh any governmental abuses of like voting rights and stuff like this so he's 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 um 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 but in his brief presidency isn't able to make any progress and so you have to wonder
if you're uh in your your unwillingness to accept reality is actually perpetuating the very reality that you seek uh to change going on to the next sort of topic how can we learn to manage our anger i was thinking about this with uh 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 uh 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 it may in the short term right and and to go to our point earlier
about sustainability is it fuel uh that 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 let me make sure i'm not lying to myself about my temper right because a lot
of us tell ourselves like oh uh 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
it's not a positive force in our lives what are the other sources of mistakes when you 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 um it's one of the passions right envy lust anger fear uh you know pain uh worry you know the 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 gonna put a two second pause on this and i'm gonna 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 pen in the eye right in a fit of rage and then he couldn't undo it yes no and it's often uh 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 there'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 okay 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 you know 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 in which case you can't afford to be angry because they're not angry right like they're pathologically evil uh or a narcissist or toxic or 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 uh 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 it's like he's inside the loop of the opponent and because they're not thinking rationally patiently strategically
they're just like yeah you know 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 two thousand 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 is that immediate uh solution the right one i think we talked about kennedy earlier you think
about the cuban missile crisis um 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 um that he allows not just his own advisors to sort of see things in 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 uh george washington is one of his favorite expressions it actually comes from a line about the stoic cakedo you know he says i want to look at everything in the calm light of mild philosophy 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 that 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 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 well 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 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 ciceros so shady man i i think it's ambition uh 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 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 opportunities 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 uh you know when it counts is both failed
by and fails uh ro the way that i read that in both books or lives of the stoic and sort of dispelling 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 uh but they don't waver they're just 100 committed to that and so often like not only like a lot of us are like ciceros 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 uh after cesar comes to power and ciceroe had up until this point been this like lover of the republic and then he just sort of rolls over and lets cesar
do what he does but he sort of kept one foot in both camps and this guy gives this speech where he sort of uh criticizes cesar to his face you know ciceroe 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 uh reveals themselves that's who i'm going to side with well so he barely survives the first
civil war uh he's always regarded as with suspicion and then the second civil war happens and then uh you know eventually uh uh it shakes itself out and ciceroe 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
um it 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 arelius and a lot of or 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 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 ourselves about who we want to be and how far we are from that at any given moment and i 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 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 it's 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 um 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 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 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 um and 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 a an ann frankline i love where she says paper is more patient than people it's also like the 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 all the ferocity of that feeling went away and so instead of vomiting that all over someone uh 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 the sink 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 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 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 i think that it also helps you reflect on the decision in total what are the variables that matter how are you thinking about it and you're getting out of that sort of like uh 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 the two or three biggest scandals of truman's presidency are basically letters he he was a reasonably controlled and decent person but when he got upset
he would write and say things that he shouldn't say um 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 and almost never send
and so i think about like there's almost never been uh uh 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 and i'm not even saying it fixed the situation but like i think about it it's like look they're still probably going to 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 right 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 uh and there's no evidence that you know no one
can go hey you're both to blame here right right because i took the time to to reflect and 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 i can't undo it yeah uh but i cannot do it again well let's sort of switch gears and end with sort of the uh four stoic virtues courage is calling is there and uh 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 the first i think uh the most let's say necessary but not sufficient of the virtues and so you know we talked about earlier
like marx real is 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 uh or more of those virtues so go into more detail though like temperament or sort of self -discipline
what what is that what does it mean what does justice mean so my uh i've only written the first book and i'm halfway through the second so my my definitions are going to get wordier as we go on because i've yet to refine them but my discipline my definition of courage is that courage is putting your
ass on the line literally or figuratively um self -discipline is the standard to which you hold yourself 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 i think justice is 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 um you know honesty respect decency fairness etc um 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 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 just 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 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 mean i'm excited and i want to know all about the timeline
on your book that's a great place to cut this up um the knowledge project is produced by the team at fernom 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 dot blog you can learn more about the show and find past episodes at fs dot
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