Finding Mastery with Dr. Michael Gervais - Why Smart People Make Bad Decisions | Ryan Holiday
Episode Date: January 28, 2026What does it mean to live wisely in a loud, distracted, and often reactive world?Ryan Holiday—bestselling author and modern Stoic philosopher—returns to explore how wisdom actually works�...�� not as a theory or a prize of age, but as a daily practice of reflection, humility, and courage.Ryan breaks down why wisdom takes work, how Stoic philosophy applies to modern parenting and leadership, and why the ability to think deeply and act deliberately might be the rarest skill in today’s world. This conversation goes beyond ideas — it’s about living wisely when life feels anything but quiet.You’ll learn:How to treat wisdom as a practice, not an identityWhy wisdom demands both courage and humilityThe key to raising thoughtful kids in a noisy worldHow to find calm and clarity in times of distraction and divisionWhy discernment is the superpower for the age of AI and misinformation__________________________________________________Links & ResourcesSubscribe to our Youtube Channel for more conversations at the intersection of high performance, leadership, and wellbeing: https://www.youtube.com/c/FindingMasteryGet exclusive discounts and support our amazing sponsors! Go to: https://findingmastery.com/sponsors/Subscribe to the Finding Mastery newsletter for weekly high performance insights: https://www.findingmastery.com/newsletter Download Dr. Mike's Morning Mindset Routine: findingmastery.com/morningmindset Follow on YouTube, Instagram, LinkedIn, and XSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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In a few short days, the brightest lights in American football will be on.
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Subscribe to Finding Mastery, wherever you get your podcast, and join us February 4th through
the eighth for game inside the games.
Wisdom is not one thing but several things.
Obviously, intelligence, it's insight, it's experience, it's understanding, it's creativity,
it's perspective, it's all these things and more, but it is not something you are born with.
What does it mean to live wisely in a loud, distracted, and often reactive world?
To me, what wisdom is, is like knowing what's what.
You got to know what is and isn't, what matters, what doesn't matter.
The reason I think wisdom matters is that all the other virtues are in some ways born from it or
informed by it.
Welcome back or welcome to the Finding Mastery podcast where we dive into the minds of the
world's greatest thinkers and doers.
I am your host, Dr. Michael Jervais, by trade and training a high-performance psychologist.
The idea behind these conversations is simple.
It's to sit with the extraordinarily and to learn, to really learn how they work from the
inside out.
Today's conversation is with Ryan Holiday, bestselling author and one of the most thoughtful
modern interpreters of stoic philosophy. Ryan doesn't treat wisdom as an abstract idea or a badge
that you earn. He treats it as a daily practice. Life is constantly teaching you and you are constantly
being exposed to all sorts of information and ideas and in some cases like real truths about the
human experience and what are we doing with the information? Are we actually translating that into
some kind of practical understanding and wisdom? That to me is what it's all about. Ryan breaks down
the four dimensions of wisdom and why parenting may be the hardest job you'll ever do without a manual.
The idea that you're just like, well, this worked for my parents and I'm not totally screwed up.
I hate that sort of uncuriosity or certainty of like, well, it didn't screw me up.
It's like, it's a screwed up person about to screw up another person.
As you listen, consider what might change if you treated wisdom not as something that you have,
but something that you practice again and again.
With that, let's jump into this week's conversation with Ryan Holiday.
I love the chance to be able to sit down with you.
And for those that haven't listened to the multiple conversations we've had before,
for me,
this is like,
it's,
I'm on a learning curve with you.
And I really appreciate the path that you've traveled ahead to bring back some of the sweetest berries
and sometimes the sourst berries that you can find to say,
hey, listen,
this is what I've been paying attention to.
So thank you again for doing the hard work and then come celebrate here with us.
Well, I'm excited. I came prepared to be mentally exhausted, which is what I remember the first time I came down here and saw you. I was like, did I just do like a two and a half hour therapy session? Like, was that an interview or did I? Did I just get examined? I don't know. I remember. What was that like? I remember we were going. Yeah. Like that was, I think maybe our first conversation. It was. I think I was still just working out a lot of stuff. You were probably just asking me totally interview questions. And I was like,
Like there's a famous Mitch Hedberg joke where he talks about.
He went to a radio interview and they said, so who are you?
And then he didn't know if he meant, he didn't know if it meant that he came to the wrong studio
or if it was an existential question.
And it's like you never know.
Some of the hardest questions I get are, so tell me what you do.
I'm like, wow.
Oh, yeah.
I can give you like the two liner or like, do you really want to know because this could go,
this could unravel quickly and I.
Or do they just ask?
actually they haven't done one smidge of research and they just want you to go like,
I'm a writer, you know?
And they're like, oh, yeah, that's right.
Okay.
Yeah, yeah.
Like, are they just trying to briefly introduce the audience or they want to go real deep?
That's always the question.
So you've got a great style about you is that you're super matter of fact.
And I imagine you might answer like, okay, are we going the short version or have you done
your homework?
I think it would just depend on how, uh, how like tired I was or how, how, how, like,
ready I was to do the thing.
You know, like sometimes, and I think
you see this in like people who do a lot of, you're
like, you see this in athletes.
It's they have the thing
they know they can say
to wrap this thing up and not have to,
you know, it's like, we went out there, we played our best
and, you know, praise God.
And, you know, next question.
You know.
Go team.
Yeah, exactly.
And actually, when I've talked to athletes,
especially when I've worked on books with them,
actually getting them past that is like a lot of work because there's this kind of like
it's almost like they've gotten used to not having to go further than the cliches.
But there's clearly like a very, usually most of them are kind of like philosophers of what they do
and they've had to think very deeply about it, especially if they've been successful at it for a long time.
But they're used to just like, you know, we did our best.
Yeah, there's different venues for that because when you always,
open up, you know, somebody who's committed to mastery, right? And you open that up, they've got
lots of ways of thinking about it. And they're really, my experience, broad strokes are always dangerous,
but they're really good by saying, I don't know. Like I'm confused by this, I'm confused by
that. But this definitely works. Like there's an openness to learning that is noted. But the marketing
mind stuff is, as soon as the microphones, they're taught, say something nice about your
competitor, say something nice about your teammates.
and take the blame.
Yeah.
You know, if it didn't go well.
Yeah.
Yeah.
Never take the glory or the light.
Yes.
You know, kind of point at others to be able to deflect and praise.
Yeah.
And that works for a soundbite, but there's not actually anything there.
And it's not really what's going on.
And yeah, then they're like doing a book or they're, right?
And you're like, this isn't that, that can carry you for 20 seconds.
Yeah.
But not an hour conversation or, you know, 300 pages.
There has to be like a real.
thing there. And then sometimes I think you realize
this is something that it's like mostly what I do is think about stuff
and articulate. That's like that's my
that's where I perform. That's my thing that I've
sought mastery in. And you go oh like you
verbal you are not verbally
expressing this stuff verbally is not what lights you up.
It's you're you have a physical.
physical gift and a genius. And you could, and just like what you're not doing is spending a lot of
time thinking about how to explain it. You're talking about the athlete in that case. But for you,
in your case, you spend a lot of time on thinking and expressing ideas. That's literally what I do.
That's your job. Yeah. So when, you know, how they get, athletes get ready for performance.
And most, not all, are pretty surgical on a process to be able to switch on. And, you know, how they get, athletes,
on their very best to give themselves the best chance.
You know, it's always a work in progress.
But how do you ready yourself for a conversation like this?
Oh, for a conversation?
Like if I'm going to do a talk or I'm going to sit down, I usually...
No, for like a podcast.
Yeah, no, I'm just saying, like if I'm going to do something, I usually, I'll usually work out
first.
Like today, I was doing a couple.
So I was like, I got to get up early.
It was raining.
It was dark.
I was like, if I don't run, then.
I won't be regulated through what will be a fundamentally
disregulating day.
So it's usually some kind of physical thing.
And then I like to make some kind of contribution to my work.
So I didn't have that much time this morning.
So it was like, let's let me, there was this thing I had to edit.
So I sat down and I edited like a piece that I was working on.
So I was like, okay, I checked off these like two boxes.
and then I can come to whatever I have to do,
both from a place of calm,
but also like not, like there's this thing I have to do later.
Yeah.
You know?
So that's mostly kind of how I think about it.
I used to not mind that feeling.
I felt like it would create the right type of internal tension
for me to do good work later.
But then as I've gotten a bit older,
I want to start winding down.
Yeah.
And so I would way rather, let's just say, work out in the morning
or do deep thinking in the morning,
as opposed to kind of put it off towards the end of the day
because I do want to, I'm competing full time
to get my sleep right.
Yeah.
There's a Tony Morrison thing where she was saying,
you know, the most important thing that writers or creators need to know
is like, when are you at your best?
And like, when do you do your best work?
And then you have to sort of design your day around it.
The famous story is that she was raising two young kids as a single mother
and she was an editor at Random House during the day.
So she was like, I have to do all my writing.
before I hear the word mom.
And so she would get up early and do it.
And she said there was something about the sunrising and whatever.
But like what I have known, found out as I get older,
is that I just do shit work after about noon.
So like anything generative, like I'm dead after about noon.
And so I have to front load the day with the writing stuff then.
Yeah.
So it's like if I'm like, hey, well, I'll do all these things.
and then I'll get to that later, I might as well just not do it.
So it's a segue.
Let's talk about wisdom takes work.
Sure.
And the simple question is why wisdom?
Why go after wisdom?
Which I think is a noble choice.
Well, I was doing this series on the cardinal virtues.
So I did courage, discipline, justice, wisdom.
So I didn't choose the virtues.
I chose to write about the virtues, but I didn't choose what they were.
Obviously, these are the fundamental principles of so.
philosophy. So in some sense, I chose wisdom because this was, it was part of this larger swing
that I was taking. I've never done any interrelated projects before. And I was creatively interested
just in the idea of like, how do you do? In the way that it's like, hey, I wrote a movie,
and now I'm going to write a multi-season television show. Like, what does that look like as a
challenge? So I was interested in that. And then, you know, there was some discretion about
of course, what order they go in. And I felt like courage made sense to be first and wisdom made
sense to be last in that it struck me as the most difficult and the one that is kind of the
penultimate of the virtues. So there was that. And then, of course, I obviously have some
discretion as to what wisdom is. Like the Stoics tell us.
us that's what they are. And there's not like, you know, one particularly clear passage from any
of them where they go, and then let me define terms. So we can only kind of deduce what it means.
So obviously that's where sort of creatively and philosophically my challenge was. It's like
what is courage, what is discipline or temperance as it was rendered it. And you know, it's interesting,
for instance, like many of the ancients and then their subsequent translators would would
call it prudence. That was the word they would use for wisdom. Okay, so right there, we're saying
that wisdom is not one thing, but several things, right? And I think that's kind of where I came down
is, you know, it's obviously intelligence, it's obviously insight, it's experience, it's understanding,
it's creativity, it's perspective, it's prudence, it's all these things and more, right? There is
something fundamentally ineffable about wisdom. And I would say ineffable as well as
elusive. Like, if you're like, here's my three-sentence definition of wisdom, it's probably
not only is it wrong, but it is illustrative of your lack of grasp of wisdom to think that it
could be so easily contained. So I think where I ended up coming down is, is on this idea that
wisdom is many things. Super helpful, by the way. Yeah, yeah. It's many things, but it is not
something you are born with. Yeah. It is something you acquire. And,
And yet, there's an unlimited amount of it to acquire.
And so I think the reason I came down with the idea of like it takes work is that wisdom
is really a method as opposed to a thing that you possess.
It's like all the virtues, it's more of a verb than a noun.
So in the same way, like, you know, it's something that you're doing as opposed to something
you have.
It's not a state that you are in.
It is a process that you are following.
And, you know, obviously this goes back to Socrates, right?
Why is Socrates considered wise?
It's not because of what he knows.
The Oracle at Delphi is implying that he knows that he's not the wisest person
and therefore possesses some modicum of wisdom.
And so it's actually in the humility or in the mindset that one orients themselves
towards being able to get wiser as opposed to
get wise.
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And it was really refreshing when it opened up the first chapter in your book.
and it was almost the first paragraph.
And you're like, yeah, probably not going to define this thing in a satisfying way.
But I will tell you what it's not.
Yes.
You know, which is cool.
That's a good counterbalance.
And I was refreshed that you didn't come up with.
Refreshed and at the same time like I was hoping for.
Sure, me too.
You know, like some sort of three-sentence pithy, you know, all-encompassing.
that being said is there's two variables that I'm really interested in the wisdom process.
I do think that people obtain wisdom.
I do agree that there's a path towards the deep understanding, if you will, is another kind of phrase.
Yes.
But I do think like at some point, it's for me, I love for you to bounce off this.
It's more than just the path to acquire or to understand deeply because I know wise people.
Yeah.
Yeah.
And when I'm around those people, I'm like, oh, it's different.
But they almost certainly do not consider themselves to be wise people.
No master calls themselves a master.
Right.
And as soon as they would, the others that are true masters of craft or self, they would say,
oh, you just exited out of the center.
Because what they are committed to is a mindset or an approach that makes them conducive to expressing or articulating some, you know, wise insight or understanding or whatever in the moment.
But it's it's not only not an in-state for them.
They are themselves not in any kind of in-state.
Right.
It's not an in-state.
Yeah.
Yeah.
There's a physicist, John Wheeler.
He said, as our island of knowledge grows, so does the shoreline of ignorance.
And so what happens is the more you learn, you're bumping into all these things that not only did you not know, but you didn't even know we're a part of it.
Like, you know, there's level, the famous John McKeith book about levels of the game. You're at a level. And then you're not even aware that there's another level until you bump up against, like you play someone who's at that level. Or you glimpse it for a second. And then you go, oh, not only did I.
I not know how to do that. I did not know that was a thing you could do. I asked it, it was a Russian
world-class wrestler, and they've got quite a system that he came through at least. Yeah. And it looked
like physical poetry when he would move. And I asked him, I said, like, what is it like for you?
Yeah. And he said, well, I don't know how to explain it, but it's like I understand the alphabet.
that. And I can put it to use. I think he's talking about his body and his technical craft. And I can put it to
use in a lot of different ways. And I said, how do you, how do you, how did I put it? It was something about
getting better growing. He says, oh, that's easy. Like I see a mountain and I climb it. And I get to the
top of that mountain. I see another mountain. So I climbed down, realizing that I didn't know very much. And then
I climb back up that next one. And when I get to the higher one, I realize there's another one.
Yes. And so he's just pointing to like, to your point, the process. Now, I would,
would not call him a wise person. He was a master of craft, not a master of self. Well, that's something
I did want to talk about in the book, because there are people who are very smart, who are also
quite stupid. And part one of the book is more or less about sort of the sort of basic, like,
how do you become a student of life, of a craft, of a thing, the sort of methodology for acquiring
wisdom? And then the second part of the book is really about,
about how you avoid most of the pitfalls that can destroy you.
And in many ways, what happens in the sort of second phase is much of what you picked up
in the first phase is now being used against you.
So like your sense of what you know is now really dangerous because you think you know something.
And so there are these like sort of traps that you people fall into and it's sort of a story as old as time.
But I'm just, I'm interested in like wisdom is on the one hand the acquisition of knowledge and insight and understanding and experiences.
And it's also the removal of flaws and biases and traps and dead ends that like historically have.
destroyed or rendered foolish many brilliant people. Like a big, obviously ego is a huge one,
but another one is just like, like sheer overwork, right? So you kind of just snap under the pressure
and stress that you put yourself on. Or you're incredibly wise or smart and understanding and
experience and whatever, but you have these kind of lingering issues from your childhood. And so now
you're a really smart scientist who's emotionally 16 and you're not subjected to the temptations
that a 16-year-old is being subjected to, but you're asked to weigh in on, you know,
questions of global significance or like, I think scientists are fascinating because, like,
obviously they're way smarter than I am and you see this, like, I just don't know how
their brain can do what they do.
And then watching, like, the petty squabbles and fights that they get into.
and their desire for credit and attention
or the number of really brilliant scientists
who fell for like scams
and conspiracy theories and nonsense
because, you know, what part of them
not only was like traumatized or struggled early on
but like is now being subjected to pressures and environments
that require a different kind of intelligence
and maybe a savvy to navigate
the political situation inside a university, or the ability to articulate or, I don't know,
operate inside a family unit. Like all these other skills are now being required. And if you can't
cut that, what you get is resentment and bitterness and frustration, all sort of really powerful
forces that can... You bring up all of the kind of modern trappings in the second part.
Yeah. When you think about the story,
Stoics, let's go back for one moment before we go too far forward.
When you think about why the Stoics chose wisdom, it always confused me.
Really?
Yeah, because that it would be a virtue.
And I'll, I differ a little bit in kind of the, oh, I don't know, maybe the premise, which is.
Of the four virtues, you mean?
Or of wisdom itself?
No, just wisdom.
that because I think that for let's take the other four virtues is that they're always readily
available even at a young age courage is available sure you know and wisdom is not readily available
and there's time under tension required usually it happens for people that are older not necessarily
you can shorten the curve but it's not at some point it becomes available at
in a small way.
And I think we could have fun and saying,
wait, maybe the kids are the wisest.
You know, it's always, you know,
but I don't think that they, really,
they wouldn't kind of check the boxes in a way that would be satisfying.
How would you take that position?
Well, maybe what we're squabbling over here is,
is like, are we saying that wisdom is what a 90-year-old
who's seen a lot of things and done a lot of things?
and that sort of like lowercase sense of being philosophical, like the big picture, they know what
really matters. Like, if that's what we're talking about wisdom, then sure, you don't have that
when you're young. But I think what we're talking about if, like, what does wisdom mean,
or philosophy means like a love of wisdom? So it doesn't necessarily mean the possession of
wisdom, but it means a love or an attraction or interest in exploring it. So to me what wisdom is,
my sort of, I said I didn't give a definition, but I actually gave a very short definition of the book,
which is like knowing what's what.
Yeah, it's a fun way.
You got to know what is and isn't, what matters, what doesn't matter.
Now, obviously, your understanding of this is going to evolve over time as you learn and study
and experience and experiment and all that.
At the same time, the reason I think wisdom matters as this virtue and why I said it's the penultimate virtue
is that all the other virtues are in some ways born from it or informed by it.
So, like, yes, courage is readily available, of course.
Discipline, temperance, you know, readily available.
But, you know, there's that expression, like sometimes discretion is the better part of valor.
So, like, yes, the courage of the young who's willing to take any risk, bear any burden, do anything,
that is a form of courage, but as you get older and you experience more, you understand things on a
deeper and a bigger level. And it's not that that should moderate your courage, but it should
direct and shape and inform it. I think a great example of this is justice. Is justice just knowing
what is right and knowing what should be done? Maybe. But I think wisdom and where
of the virtues all inform each other is like, okay, but what can you do about it? Where can you bring
it in the world? And there is this kind of idealistic, youthful sense of justice that's very black and
white. And then there is the justice and the sense of ethics that it's not that it's situational
and that it's always willing to compromise, but it does understand that we are imperfect people
in an imperfect world. Like one of my favorite lines that's an illustrative one in Marx's
his meditations when you go, this guy's the emperor of Rome. He writes, like, remember that you don't
live in Plato's Republic. And so, you know, philosophically, what you know or what you would like
to be true is very different than somebody hands you the keys to an empire slowly, painstakingly,
brutally and violently assembled over centuries. You know, if you think that you can change it like
that and magically make it what you want to be, what you're ignoring, what your lack,
your sense of right and wrong could be totally dialed in, but what you're lacking is the
wisdom to understand why it is the way that it is, which is to say what were the compromises
and accommodations and painful acceptances that shaped and informed the thing. And so often,
like, what you see, like some of the most dangerous movements in all of history have been,
like youthful revolutionary radical groups that think they can that that humanity it just needs
some more information and some nudging and then it will become so do you see what I mean like
what wisdom I think is is something that evolves over time but it's it's it has to inform and
shape the the other virtues because otherwise they are something impractical entitled even like
petulant and dangerous.
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Yeah, I think that, like, at one level, I can fully clump them together and be like,
yeah, those are great.
Yeah.
You know, those virtues are wonderful.
You know, I understand why those would be, you know, at the high table.
I just think fundamentally that one's just a little bit different than the others.
Yeah. And so I want, however, when I think through them, you know, courage, justice,
you know, discipline that it's not like you add those up and you get to wisdom. So it doesn't work
that way. No. And it doesn't mean that if you are somebody who's on the path to acquire
or understand or inhabit, the complex made simple, the universal kind of insights about how things
work that all of a sudden you're going to have the opposite. You're going to have courage.
I think you've got to practice courage. You've got to build it. So they don't quite square,
but I like them. I'm not in any way disagreeing, but I just point out, like I've always had a
little bit of a hanging, Chad, like that one's different. That's a great. Yes. What's interesting
about it is Zeno, the founder of Stoicism, 2,500 years ago, who first lays down the virtues.
you know, Aristotle had a few more.
He picks these four.
Yeah.
Yeah, and then I think Ben Franklin had 12.
Like people are always, but he picks out four.
And he says they are distinct yet inseparable from each other.
Which is kind of the perfect way of expressing it.
It's not like, as you said, the first three add up to the fourth.
And in fact, you can put them in any order, but you really can't remove one without
fundamentally altering the others.
and you see how one has to inform and shape the other. I do think they're related in a couple ways.
As I said, they're all born from wisdom in that wisdom has to explain when and how to apply them.
At the same time, you subtract justice from any of them, and you're dealing with some real problems.
I'd also say, you know, it takes courage to bring any of the four into reality, right?
like the decision to sit down and pursue wisdom in a superficial, even foolish world takes courage,
or to decide to be yourself and do what you think is valuable, you know, takes courage.
So they all shape and inform each other.
Where would they be without the willpower or the discipline to, you know, execute on them?
It's a nice way to think about it, yeah, which is you're nodding back to, you know, 2,500 years ago,
the first insight, you know, around it. And I'm not sure if you said it, if you meant to say it,
but I want to just highlight it. Were you talking about yourself when you said to sit down
and write about courage in a foolish world? No, no, I meant to sit down and be interested in
wisdom in a foolish world. But are you talking about yourself there? Or are you talking about one of the
Stoics? Well, I mean, I did, I think I say this in the afterward that like this didn't exactly
feel like I'm hardly ranking it in the, you know, the sort of pantheon.
of courageous acts. But like the decision to sit down and write a book about wisdom, there is
something scary about that. You know, like, it's, it was scary to me, which is I guess I could
say that with certainty. I'm not asking for anyone else to pat me on the back. I'm just saying,
like, I was intimidated by the project and I did it anyway. Why is that? Why is it?
Well, you know, I mean, I was intimidated the first time I wrote about socialism at all. I, I'm a
college dropout who's largely self-taught. Like, I don't have the security.
or the confidence of like, oh, I have a degree in this, like, you should listen to me, right?
So there is, anytime you're doing something that's outside your comfort zone, that's what
we're talking about when we talk about courage.
But I just mean, like, the idea of, like, hey, I'm going to, I'm going to go learn about
something.
I'm going to take seriously that there is such a thing as wisdom, and I want to get as much of it
as I can. I feel like that is a courageous act in a world where most people operate on the surface
and don't ask a lot of questions. So I think there is something courageous for anyone who's like,
I'm going to go back to school or I'm going to pick up a book or I'm going to figure out why
things are the way that they are. Yeah. Yours difference between school and picking up a book and
yours is that yours is wildly popular, like, you know, scrutinized and observed.
And, you know, even so much that you had a talk that was controversial at an academy.
That did happen. Yes. Yes. I do want to come back to that. Okay. Let's stay on wisdom one more
turn here, which is you did a deep scrub of one of the most important attributes for me for a person to
be able to walk the walk and talk the walk is that they need to really understand.
understand what's what to use your language and then have the courage to be able to act accordingly.
So I love that you went after it. What do you hope that we understand from the most simple of,
you know, hopes and desires? Like, what do you hope we'll understand from reading it?
What I felt like my contribution was, was the idea that wisdom isn't, okay, so we go like,
hey, wisdom is a thing that takes a long time, and, you know, mostly older people have it.
So is it just a function of sticking at this life thing? I mean, absolutely not, because I've met a lot of
stupid old people, too. And so, like, I dislike this idea that wisdom is a natural byproduct of
being a sentient human being. It's certainly not. Somebody had introduced to me, it was in college,
and I just loved it. There's three paths. I already know.
that they're a reductionist, but it was a fun statement. There's three paths. The path
to be an old fool, a bitter old fool, or a wise person. Yeah. And I heard that early,
and I was like, wait, what's an old fool? Ah, they just constantly chased all the external
pleasures of life. Yeah. Bitter old fool, they chased them, but didn't get them. And then the
wise person is somebody that worked from the inside out, that really wanted to understand how
things, people experiences, like what's sitting underneath of it, make it universally available.
and take the complexity and make it simple. And I was like, oh, that's the path of like joy and
happiness. Totally. Purpose and meaning. That's it. And so that's why I was really pleased that you
added to the body of work there. Well, you know, I think people go, you don't like,
books are inferior or insufficient. You've got to learn by experience, right? And it's true.
Experience can teach a lot. But it's not a given that experience teaches. I mean, people are having
experiences all the time every day of their life. And wisdom is exceedingly rare. So it is certainly
experience can teach. It is necessary, but not sufficient. And so there's this great line,
Churchill often had the way of just getting to the essence of things. He was talking about
Neville Chamberlain, who, like he didn't know just as this one guy who made this one bad
decision at Munich, but like his perpetual political foe. And I think he said,
of Chamberlain, this was a man who occasionally stumbled over the truth. And when he did,
he picked himself up and dusted himself off and carried on as if nothing had happened. And so,
I would say that describes a lot of people. Like, life is constantly teaching you, and you are
constantly being exposed to all sorts of information and ideas and in some cases like real
truce about the human experience. And then most people don't even observe that anything is happening.
Are we becoming less wise? I don't look back at history and go, humanity really figured it out
back then either, right? Like, if in any, in some cases, I think collectively we're getting
wiser than we have been before, and then in other cases we're getting much stupider, I do think
there were certainly wiser people of a type that perhaps we don't see so much anymore. But I'm not
that interested in whether like the trend lines of wisdom. I'm more interested in like individually,
like in our own journeys, are you and I getting wiser? And what are we doing with the information,
whether it's from a book or a lecture or, you know, hard one experience? Are we actually translating
that into some kind of practical understanding and wisdom. That, that to me is what it's all about.
And I think anyone who's actually done the work, you realize, oh, you read about stuff or somebody
tells you something, and then you have experiences, and those experiences are shaped by what you
bring to them. And then what you bring to them is also shaped by what you take out of the
intersection. And so the subtitle of the book is learn, apply, repeat. It's this kind of infinite loop
of you hear about something, you try a thing, and then you come away with a combination of those two
things that is unique and special, and then you go learn more. And that's when we're talking,
what is the method? That's the method. Yeah, it's, I saw the subtitle and I understood. And I,
you also point to the method that I'm more aligned with, which is, it's a path of deep concentration.
Yeah. So when you deeply concentrate,
deep focus, if you will, on a thing, you end up understanding that thing.
Yes.
I don't think there's another way other than deep concentration.
You might hear somebody say something like, I don't know, fill in the blanks, whatever it might be, but it's not yours.
It's theirs.
Yes.
So you have to really grok and deep focus and concentration.
And then you start to understand something.
And then you get like this insight, like, ah.
So concentration to insight.
And then when you couple of insights together, like, oh, wait, that's how this works.
And that's how that over there work.
Wait a minute.
And you have connections between the insights.
Oh, wait.
Yeah.
So that's where you reveal wisdom.
Mm-hmm.
So.
And then also, then you create a theory or a plan and you try to do something with that.
And then some of it works and some of it doesn't.
And then there is that process of reflection again, the debrief.
That's the repeat, you said.
Well, no, I just, I think you, it's learn a,
Like, if learn, apply, reflect, repeat.
Reflect.
Right?
Is probably how I would say that the important thing that people miss, right?
It's not just like, hey, I read a lot, so I know a lot.
I do a lot, so I know a lot.
It's a combination of those two things.
But then it's this process of, well, what do I know?
What am I feeling?
How am I discussing and analyzing and reaching conclusions out of this?
Like you think about, right, coach has a plan.
trains the players and everything. They practice it. Then they do it in the game. And then what do they
do on Monday is they, or Tuesday, is they sit down and they break down the film of what happened.
And they, in some cases, it's like, look, you fail because you didn't execute the plan.
And in other cases, it's like, hey, the plan was insufficient. Here's the change we're making.
But wisdom is that process. That is the cycle that you're repeating. And so who you were at the
beginning of the season should be inferior to who you are at the end of the season, and who you are
at the beginning of your career versus who you are at the end of your career should be transformatively
different, and you're repeating miniature and macro versions of that in all aspects of your life
all the time.
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I have a first principle that life is pretty hard.
Sure.
Yeah.
It's thorny.
You know, there's lots of trap doors.
It's not designed for our happiness, our joy.
It's not even designed for our survival.
Yeah, no, right.
Our brain is like optimized for it because, you know,
know, it's dangerous out there.
And most, I think most people have a pretty lonely experience.
And I'm not talking about the loneliness of despair and the loneliness of depression.
I'm not talking about that.
But there's a uniqueness to your experience and my experience that is nearly impossible
for me to express my fullness of my experience in life.
So it's contained or trapped inside of me.
Sure.
And if I don't really examine that and have a way to,
express it externally, it is hard to connect with other people. Okay. And I'm not talking about
depression or despair, just to be clear. So with that kind of assumption, if you will,
how do you think about life in general when it comes to the path of wisdom, the dearth of wisdom,
the state that we're in, you know, based on what you've studied from the Stoics and
and kind of the modern contemporary understandings that you're...
I would agree life is extremely hard,
and it's harder for some than others,
depending on where and when and how
and what sort of hand you got dealt.
But wisdom isn't just this thing that you acquire
from your own lived experience.
That would mean we're figuring everything out
for the first time every time.
What's it called 52 dates?
Yeah.
Seneca said, you know, the whole point of philosophy is that it allows you to annex into your life
all of the wisdom and ideas of the past. And so it seems silly that you, like, obviously you come
out of the womb knowing nothing and having access to nothing. You're just like this. You might as well
be the first person ever born as far as you understand it. But then very clearly and quickly,
you realize, oh, there's other people. They went through the same.
thing. They know a bit more than me because they're further along the path. And then you realize,
oh, there's some people who've really got this life thing figured out. I want to, like, learn from them.
Maybe that's your parents. Maybe it's not. And then you go, oh, but also every person who has ever
lived, what did they learn? And what collectively is society is a species have we figured out.
and you realize that's where the transference of wisdom comes in.
And stoicism is founded around this very idea.
Zeno, the founder, he is this merchant.
He's traveling around the Mediterranean,
and he stops at the Temple of Apollo in Delphi,
which I was just at, and you come in from the sea
and you wind your way up to the top of this very tall mountain,
and you wash your hands at the sacred spring,
and you make your way up the sacred way,
through these shining temples that every Greek city state
had put up in honor of a victory or the gods,
you make your way of the temple of Apollo,
and you would light this incense,
and then the oracle would come out
probably high off these vapors that came from the ground
and give you this kind of mysterious enigma or riddle
that you were supposed to sort of use to answer your question.
And the Oracle of Delphi tells him that wisdom comes,
you begin to have conversations with the dead. And he doesn't know what this means. And so he takes it
back with him. And it's not until he washes up penniless in Athens in the Agora, which again,
you can walk through to this day. And he hears a bookseller reading out loud, a scroll of a story
from Socrates. And it's in this moment that he realizes that that is talking with the debt, that books
are a way to talk with the dead. And indeed, we sometimes call the great texts of
the ancient world, like the great conversation, because you're talking to Plato and Socrates
and Aristotle and Zeno and Marks, Ruelas, and Seneca, and Homer and all the great thinkers of
the past, that it's a conversation. But mostly what it is is it's a transference of wisdom.
Like, these stories were supposed to be entertaining, yes, and provocative sometimes, but mostly
they were supposed to be like, here's what we figured out. We learned this or that.
what about this? You know, here's a question. And that's, that's what wisdom is. It is starting from
everything up until now and then adding to it. And it's this kind of perpetual journey that we're on.
It's cool. It's the ultimate passing the baton. Yes. And the idea is if you should leave it a
little bit better than you found it. What are you adding to the store of knowledge?
in our modern world to me my my account is that wisdom is at an all time in my life low it feels like
probably you know and this is there's a bias here listen i've only lived a half a decade sure i have not
lived the you know 250 000 300 000 years of whatever so that being said um why do i say that is
the bias is that there was a much simpler time before something
cell phones. And there was a bit of a, I thought about this when I was reading your book about,
like, what are you yearning for? Because when I read the ancients or anyone before me that has
helped, that I think will or has held up for the ages, there is just this feeling and there's
this kind of thing that washes over me, God, it's so wonderful to like, to really learn what
they learned and to be a student of that, to try to understand the context of what they're
dispelling their information from. And it pulls me back to a much simpler time, which was like
before the cell phone for me was this demarcation. And I know that, you know, we're going to, of course,
there's a question of AI in here somewhere, but what are you, what is it that you're yearning for?
Because that's what happens to me when I go back and read, you know, the ancients.
Well, I mean, look, you can tend to think of, you know, the time of Socrates as this golden age where people walked around in Togas and, you know, just talked about ideas.
But also, you know, Socrates lives through a great power conflict, like akin to America being in a 40-year war with China.
And he fights in the war.
his city loses the war, you know, and then Athens is ruled not by a tyrant, but for a time known as the 30 tyrants. And then he's put to death by his fellow countrymen. So for like asking too many questions, basically, right? So like humans have always been humans and always done things like this. And it is kind of not refreshing because it's a little sad, but like some of the oldest bits of culture we have, like there's this.
from like 4,000 years ago or something, and it's like complaining about kids these days.
You know, like every generation is worried about the previous generation and worried about
the current state of things. I mean, is there something kind of anti-wisdom about social
media and our phones? Yes, I think so. It's not the most conducive to consideration and empathy
and patience and big picture and collaboration.
It's bad. I would certainly stipulate that. Is there something I'm yearning for going back towards
no? And I, to answer your question, and I think it brings it together, there's a great line from
Blaise Pascal. He says, you know, all of humanity's problems stem from our inability to sit
quietly in a room alone. And so I would say I would like to do that, you know? Am I really able to
do that? No, not even close. Is that partly because of my phone? Sure.
But is that because that was a problem 500 years ago also,
and it's a fundamentally human thing.
And I think it's fundamentally a youthful thing that you tend to find as,
like one of the things I admire about the older people that I know is their ability to just sit there.
You know, they're just,
they're just operating at a slower pace.
And it's not because they're physically not capable of a faster pace so much,
or mentally not.
they're just, they just realize how silly some of the rushing is.
One of the wisdom teachers that I'm fond of,
I asked her what she's working on and she said,
returning to innocence.
Ooh.
Yeah.
And it just,
what do you mean?
She says,
well,
I just want to return to that innocent part of me that I've lost.
I love that because one,
and I talked about this in the justice books,
one of my least favorite expressions is this one that is,
if you're not liberal when you're young, you have no heart.
And if you're not conservative when you're older, you have no brain.
Again, this is lowercase L and lowercase C, not exactly one party or another.
But I hate the implication that you're supposed to become more cynical and hard-hearted as you get older.
Right, yeah.
That you're supposed to be less interested in other people and trying to fix things.
Like, what I really admire, and I can think of a few people specifically,
but I really, really admire the old people that I know that are still very social justice-oriented
and very empathetic and kind.
They're worried about, they're not worried about protecting their things.
They're worried about, they're like, I'm already good.
I'm worried about young people, and again, not like the young people suck,
but like they're worried about the sake of younger people.
Speaking of younger people, parenting is, you know, I know that you're one and I'm one and so many of our community are. It's a tough one. It's the hardest thing you've ever done and you've never done it before and you're only going to do it a few times.
That's right. Yeah. I have one son and I think a lot like, oh, if I had a second go, I'd be, I would be better, you know? But anyways, what would you point?
parents to understand a little bit better based on, you know, your research on wisdom.
Well, first up, that it's something you should try to learn about and get better at.
Like, just like, oh, I, the idea that you, look, I do, I do understand at some level,
this is like a biological thing and your instincts are pretty good.
But the idea that you're just like, well, this worked for my parents and I'm not totally
screwed up. I hate that sort of uncuriosity or certainty of like, well, it didn't screw me up.
It's like, that's a screwed up person about to screw up another person, you know?
That's right. So like having a curiosity and an openness and in fact feel a compulsion to try to
break various cycles to do it differently, to do it better. That isn't to say you turn it
into a second job that you're trying to win at because it's not something you win at,
but it is, how are you treating this as similarly to how you would treat anything that you
are trying, which is like you're trying to do it well because the stakes are high. Yeah, that's right.
And that there is a lot of, I mean, this is the thing we've been doing the longest, and we have a lot
of lessons about what works and a lot of lessons about what really profoundly doesn't work. And
how to think about that.
Like, one of the reasons I wrote The Daily Dad is, like,
I thought it's weird that you're supposed to,
like, when you, your spouse or you get pregnant,
and they're like, read these books.
And then they're like, like, you're supposed to,
you're supposed to do, like, nine months of reading,
and then you're just like, good, you know?
And I really hated that even when I was reading those books,
it's like, it's like telling me about how I'm supposed to do something
15 years from now, like I'm going to remember any of it.
In fact, it has to be this kind of ongoing conversation in the way that you might belong to a professional group or an association or you might attend a conference.
Like how many parents would ever go to a conference about parenting or would even, yeah, like are actively looking for and trying to acquire wisdom to make them better at this thing that they're doing?
Not many.
Yeah, and that's really sad.
It is said, yeah.
But we go to professional conferences all the time.
Yeah.
Yeah.
And yet you go, but I do it all for my family.
You know, or like, they're my number one priority.
And it's like, is that what your calendar says?
Is that what, if I could look at like a breakdown of your thoughts?
Is that where most of your thinking was?
Or is most of your thinking at like, how do I make more money?
How do I get this person to like me?
You know, I even think about something I struggle with, even with stoicism, it's like, look, I'm pretty good at not being rude to people in line. I'm pretty patient with the people that work for me. I try to just be a good person in the world. And then I get home and I'm like, I'm out. You know, like, how many of us are saving and actively working? Like, how many of us are our best self at home or our best behaved self at home? Right? Because
You tend to give the leftovers to your family.
And then you pat yourself on the back and go,
I do it all for them.
They're my number one thing.
That's my most important job.
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Yeah, as you say it, I see myself in that.
Like, it's the ultimate kind of trickery.
Yeah.
you know, like to feel good about myself as I'm leaving home to go travel again.
Yeah.
You know, and I say, you know, it's the strike while the iron's hot is something you'll hear me say,
which is, I believe that.
Yeah, sure, of course.
Yeah, why not?
You know, family's number one, but I'm away so much.
Totally.
And, you know, I do think it requires an excellent partner in somebody who knows how to take care of
the things that you're not able.
to take care of.
Yes.
And it's,
but it does need to go both ways.
I need to take care of the things that my wife can't take care of.
Sure.
Or,
you know,
doesn't want to and,
and vice versa.
And then I feel like you got,
you got a little bit of a team.
Call it a family.
But it's,
what are some basic practices that you think would be important?
Obviously,
sort of always be learning.
And then,
um,
how are you in the same way that if you were on a football team or you just had a sales
meeting, you would do your best. You'd try to do the thing. And then afterwards, you'd be like,
all right, well, why did that go horribly? Or like, why did that go well? Yeah. And I think those
moments before bed, you're both exhausted. And like, are you watching TV or are you going,
so why was that so rough? Or what did you need? Or what, you know, like, the conversations of like,
how are we getting better at this?
And then how are you getting feedback from like person that really matters,
which is them, the kid, you know?
Like, and usually your kid, you know, your kids aren't giving you progress reports.
But they are saying things, you know, from time to time that really tell you a lot.
Well, you had a great insight.
Your kids are not going to do what you tell them.
I'm paraphrasing.
They're not going to do what you say, but they're watching you.
Sure.
And behaving accordingly.
Yeah.
We're like, look, this is a way.
it's real practice. You want your kids to love learning, right? You want them to take school seriously
and to learn. Whatever have they seen you learning? Or would they define adulthood as a person who does
not have to go to school anymore? You know, I think the framing I have often for my son is that
I think it helps me a lot is when he watches me, is he thinking adulthood is awesome.
Yeah.
Parenting is great.
Being in a relationship is the thing.
You know, is he like, yeah, like I'm looking forward to that phase too.
Sure.
Or is he going, forget it.
I'm not doing it that way.
You know, right?
Probably both.
Yeah.
But I just, it's like, are they seeing you do the things that you want them to do?
And wisdom is a great, like, what are they seeing you struggle with?
What are they seeing you trying to learn?
Who are they seeing you being taught by?
How is curiosity and learning and a lifelong,
commitment to those things, something you actively model, which again goes to the point of
wisdom is a verb and not a noun. Yeah, that's very cool. When we think about AI, kind of a new thing that
humans are trying to sort out, and it's the timing of wisdom meets AI is awesome. And how,
meaning the launching of your book with kind of the beginnings of the throes of AI. Who knows
what it's going to look like in five years. How are you thinking about AI? I can't imagine a technology
that would require more wisdom than this, right? I think people think it's this replacement.
It's this, look, it's the sum total of human knowledge. It can solve these complex problems.
It can answer anything, sort of. But without a broad liberal arts education or a sense of how things work,
what bullshit is or isn't, what separates a good answer from a bad answer, what matters, what doesn't
matter. This thing's going to eat you alive, man. I'm terrified. Like, I know a few things about
psychology. Yeah. And so I'm playing with it and I'm asking questions and I'm like, well, that's wrong.
Confidently wrong. Like, yeah, confidently wrong. Or, well, that's really incomplete.
Yes.
You know, so my my guidance to folks is like, do not give too much credence to what is coming back
because from somebody who spent their whole professional life understanding the science and
the applied science of psychology, it's not good.
No, look, it is, it is a commercial product.
So it wants to make you happy in the way that it wants.
but but it's it is it is not going to say I don't know that's beyond my capacities I'm bad at that
it might say oh I can't do this thing because I'm limited by copyright but it's never going to say
that's a complex thing that a computer is bad at at being able to give a good answer to and
therefore I'm not going to try or therefore any attempt to answer would cause more confusion
than it doesn't then it would it would reduce blah blah blah and so the
the numbers, the number of times I get confidently incorrect answers or just laughably bad answers.
But again, how do I know that? It's because I know how this question that I'm answering,
I might not know the answer to the question that I'm asking, but I know how the answer should be found,
or I know the ballpark in which it should exist. And that is the result of my experience and
understanding and insights. Like, AI can help you find a quote.
but if you don't know what the quote is that you are looking for or what it's about or what it's
supposed to be expressing, you might as well just be spinning a roulette wheel.
You have to have this, I can have it help me break down something or locate something or
add a little color to something, but it really can't do the main work of thinking of being a person.
In fact, that's a more important skill than ever.
Yeah, and I'm not anti-AI.
I think that there's a great utility in it.
We have to figure out what it is and how to use it.
Yes.
And until then, the Dunning Kruger effect is actually running the show.
Well, and I've spent a lot of time with my kids, like, sort of teaching them how to use it.
Because the different-
How old are your kids?
Nine and six.
Okay, cool.
So, like, you know, like, let's come, you want to color?
Let's have it create something cool to color.
Or, oh, you want to know?
more about something like this. Well, let's ask it this question. My son's obsessed with The Odyssey.
And so he asked me this question that I didn't know the answer to. So I was like, well,
well, let's ask chat Chb-T and it's answering. And then we're discussing whether that's right or not,
or whether we agree with that answer or not. But like what they call prompt engineering,
it requires no small amount of intelligence and wisdom. Like a good question versus a
bad question determines whether you'll get a good answer or a bad answer. And understanding how to do that
is going to be a skill. So I see it as a tool like any other. And if you're instinctively rejecting
a tool, you're, you know, that's anti-wisdom. And if you think the tool can replace having to
do the thing, also anti-wisdom. Yeah, that's cool. Right? Like, you need, like, tools can make you
better at what you do, but you have to understand how to use the tool.
There's five sources of power in the Buddhist approach, one of them discernment.
Yes.
And, you know, it feels like a superpower to have the kind of wherewithal to discern.
Does this make sense?
Does it not make sense?
Yes.
And the only way to really have discernment is to have lots of reference points.
Yes.
And to have some sort of internal reference.
point as well. Does this fuel seem right to all of this interesting life experiences, external
reference points that I've had? And it's AI, one of the things that's robbing is some discernment.
So I'm saying we need to flex, and I think you would too. We need to flex even more into the
building of discernment. You need to have the discernment to be able to effectively use the tool
and also to effectively protect yourself against the tool. We're going to enter a world of
AI slop, just unendless amounts of nonsense and equivocation and personalized sort of information
designed to make you think this or that. And if you don't have the ability to know like a good
argument from a bad argument, I think you're just, you're going to get into it. And look,
people were already, we wouldn't be in the mess we're in currently, politically, socially,
run down the list of all the way as society is struggling, if people were really good at that.
Like, people are really bad at knowing the difference between the onion and a real news website
to say nothing of a bad faith news website and a journalistic outlet.
I mean, look, something like 15 or 20 percent of the American population thinks that
chocolate milk comes from brown cows.
Not true.
That is a rough starting point to then, you know, do.
deal with a technology that wants to tell you what you want to hear, you know, or that requires
discernment and intelligence to be able to tap into the considerable knowledge that it, you know,
if you think chocolate milk comes from brown cows, you're going to have trouble turning on
your computer, and then you're also going to have trouble, you know, making sense of what
it's selling it. So on the kind of combination of a couple virtues, certainly,
courage and wisdom, how are you navigating the political, your ideas on the political spectrum?
If you say something, you're on the, you're on the cancel culture from 50%, and you say something else,
you're on the cancel culture for the other 50% and being provocative here for a little bit,
but like how are you navigating the political world when I feel like the job of each of us
is to call a spade a spade and to say what is obvious.
Like, I say this in the afterward of the book.
Like, I'm not saying I'm the wisest person on the world,
but I'm proud of the fact that I'm fallen for the,
like, the biggest con of our time.
I don't think, you know, like, it's obvious to me that Donald Trump is what
Donald Trump is.
And he is your classic demagogue, con man sales artist,
or a con artist salesman.
And that isn't to say that some of the things, like, this is what con people do,
a conmen do.
Like, sometimes what they're selling is good.
Sometimes it's not good.
Sometimes it's a mix of all of those things, right?
So, like, what a demagogue does is speak to real grievances.
They just sell unworkable, manipulative solutions to those grievances.
And so, you know, like, sometimes your first reaction to things is about as spot on as they get.
And when the host of The Apprentice runs for President of the United States, a person who has literally never read a book, like once in the – try to find an example of a book that Donald Trump has read.
Like, the only book he has ever spoken about having read was a book – there was a profile of him in the early 80s.
where he has like a book of Hitler's speeches on his nightstand.
Oh, my gosh.
So, like, this is a dark, I think there's a dark story that, like, some smart people I know
have managed to fool themselves about.
And then some not-so-smart people have found themselves, you know, manipulated by,
which is the story as old as time.
So, like, I don't, I don't dance around it.
I don't, I don't know exactly where we are on the timeline, but it's not a good timeline.
and it's, I think it's imperative on each of us to say that, you know, and to not sort of
hedge our bets. Do I make everything that I do about this? No. But like, if you were to describe this
to someone and remove the identifying features, they'd be like, like if you were saying this is
happening in another country, or you're just to describe the sort of characteristics of that person
and be like that. I think about, there's a story about Kennedy. So again, this is not a partisan thing.
There's a story about Kennedy. Kennedy's on all these crazy medications when he's president,
because he has Addison's disease, and then back in the 60s, they'd just be like, here's an
upper, here's a downer. He was on these, like crazy drugs. And a doctor finds, one of his doctors
finds out all the things he's taking. He's on this antipsychotic, I think, at one point. And he goes,
no person with their finger on the button should be taking anything like that. And so you go,
what characteristics, what background, what kind of temperament do you want in the person who
controls the largest nuclear arsenal in the world who holds in their hands, not just the
life and death of billions of people, but also the potential flourishing or suffering of billions of
people, you would want the opposite of what we're currently having. And I don't think that's a political
argument. I think this is an argument about just sort of what it requires to do the thing.
When you look at the virtues that you've studied and written about, do you think he has,
what is your assessment of those virtues? I mean, look, you get nearly assassinated and you get up
and you say, fight, fight, fight. Is there a modicum of courage in that or even a lot of courage in that?
sure, but, you know, the virtues can't be separated from each other. And so to just be physically
brave in one instance, after, by the way, essentially a lifetime of no such courage, I'm not that
impressed. You know what I mean? Like, it's not that, let's just say it's, it's, it doesn't
substantially change the equation. And you have to ask yourself, what role do you want to play in that?
Some people, and I know some of them personally, I know some of them personally quite well.
People have said, well, you know, I think I can get something out of this.
Or I think this will be good for me in this one targeted area.
Or, hey, you know, I've always really, really wanted to be the director of the CIA.
So I'm not going to lift, you know, this is what I got to do to be the director of the CIA.
And that's just a random example.
I don't actually know the director of the CIA.
But I mean, I know people in equivalent positions.
Yeah.
And I know what they actually think.
And so I know the tradeoff that they made to get the thing they say they wanted.
I've got lots of folks that have said to me, you know, I kind of thought I knew what I was
voting for.
Yeah.
But I didn't think it was going to be like this.
Which is hilarious because he said it would be like this.
And so this goes to our point even about chat GPT is like, if you lack the ability to hear what is being said explicitly or implicitly.
you're going to have a rough go of life. And so, you know, our endless capacity for self-deception
is one of the most incredible and terrifying things about the human condition, right? Like,
I'm saying the words out loud, but you're not hearing the words because you want to hear
X, Y, or Z. Or you're, you know, I think about all the ways that we make ourselves stupid. And I mean
that, like, when you have a grievance or you have a resentment or you have,
a singular thing you're focused on can be very hard for you not to see the other things pertaining
to that. And that's kind of what's happening or what has happened, you know. And so look,
none of this is particularly new. And there is an analog figure in almost every era of history.
I collectively I think the wisdom of the founders designed a number of checks and balances that were designed to prevent a thing like this from happening.
But it failed in this instance and it it or or it didn't fail but we failed it and now here we are and where is it going to go?
I don't know, but I'll say it certainly tests my stoicism to like navigate that day to day.
And I think the good news is the stoicism, the stoics were tested in that way too.
I mean, Seneca was in the time of Nero.
Cato saw the rise of Caesar.
You know, like, as I said, the Athens of Socrates was not a wonderful place or he would have lived a little bit longer.
Yeah, and when you think about the clarity in which you're sharing your ideas, you are not concerned about alienating people that would see it differently.
I mean, I would prefer that it didn't, you know, and I do.
understand that it could, but I think, like, what is the job? What is my job? Like, my job is to
say what I think. Yeah, that's right. And my job is not to preserve my audience for the sake of having
an audience. And this is, I mean, this obviously gets into some of the ideas in the courage book,
but, like, when you live in a world where everyone is preserving their options for a future date,
you have what's called a collective action problem. And we are in the midst of a large collective
action failure, which is at every point we could have done something about this and we didn't.
And in fact, we plunged deeper and deeper into it. And it's going to cause and has caused
untold suffering. There's a reason we had like the highest death rate of any of the developed
countries in a pandemic. It wasn't preventable, but it could have gone differently. You know,
there'll be other things like that and there have been other things like that. And like,
like, I'll be pretty fine. You'll be pretty fine. Probably. I mean, we could all die in a
horrendous, you know, nuclear incident. But like, chances are, you know, that poem about like,
first they came for, first they came for. Like, we're pretty high on the list, like, or low on the
depending on which order you're coming from.
But like for the most part,
the, it's not people like you and me
that are the most susceptible
to the kind of agenda that's on the table.
Yeah, I mean, the most vulnerable
are probably the next generation.
You know, as of today's recording,
our coral reef is now hit the tipping point.
As of today, you know,
meaning that we're on the downhill slope
of one of Mother Nature's great checks and balances.
Yeah.
No, I mean, just the nature of like,
worrying about climate change is almost a quaint
concern when you have five other five alarm fires happening right in front of you.
And that says, that says something about the pretty dramatic shift that we've had.
But anyways, I guess like, I feel like, I feel like my,
job is to say what I think is obviously true. And there's a, there's a line Stefan Zweig had about
the thinker Montaigne who's a character in the wisdom book. And he said, you know, like,
Montane shows us that our key job is to remain human in human times. Like I think like to not become
an asshole, to not be degraded by or part of the sort of mob or the viciousness or the cruelty.
That is like the primary struggle. Because if you lose that, you lose that, you know,
that, then you lose most of the other things. Was it Montaigne in your book that you, I think it was
him, but it might have been somebody else that you illustrated this story about his dad showing or
being a great teacher. Yeah. Meaning like there was, I don't know, let's go, let's go learn this together.
Yeah. Was it his dad? Yeah, he had this incredible, like very special education. But like, you know,
he lived in the time of the religious wars of the 15th and 16th century. And it was a horrible,
violent, like, awful place.
And, like, the struggle was to not be part of that.
Like, the first thing is just not, like, when the mob is stoning someone to just not
pick up the stone.
And then obviously the next part is, like, how do you save that person or how do you
participate in creating a society that doesn't do stuff like that anymore?
But, like, if just everyone individually didn't pick up their stone, that also solves
the problem.
And so, like, it starts there.
And so virtue is, especially justice.
Like, justice isn't this thing that you get.
It's the thing that you get.
It's a thing that you live by.
And it's taking your, like, most of us are not president.
Most of us are not senators.
Most of us are not.
But, like, each of us does have a certain amount of discretion or influence or
some individual decision has come down to you.
And how is, how are you going to act?
How are you going to act?
What are you going to do?
Ryan, this is awesome.
thank you for a discourse that is serious.
It's complicated.
It's thoughtful.
And you navigate the nuances really well.
So thank you for that.
And I have one question.
I said I come back to it,
but you had a talk at a Naval Academy that was, I think, canceled.
So I was supposed I had been doing a series on the Cardinal Virtues to each incoming class at the Naval Academy,
which has been, by the way, one of the honors of my life.
these are like, if there's anything that gives me hope, it's you meet that class and you're like,
these are the, none of these kids have to be here.
Like, these are the best and brightest young men and women from all over the country.
And getting in is really hard to do.
It's extraordinarily hard, but because it's so hard, they could also be at Harvard or Yale
and looking at, you know, an unlimited Wall Street, you know, career afterwards.
And they chose to be here.
And by the way, this is only the beginning of a multi-year commitment that they have to make.
And so I've been doing this series on the Cardinal Virtue. So I did courage, I did discipline,
I did justice last year. Mostly I talked about Jimmy Carter, who was one of the most famous graduates
in the Naval Academy. And so this year I was going to talk about Admiral James Stockdale,
who was also in Carter's class as an example of wisdom. And one of the stories I've been planning
to tell was about Stockdale's time at Stanford, which he went to in the middle of his career.
He's a great fighter pilot, and the Navy sends him to get a master's.
degree, and he takes a course on Marxist thought, comparative Marxist thought, where they only read
Karl Marxists. They read the Marxists, not like thinkers about Marxism, but Lenin and Marx
and in the original. And so he is like in the early days of the Cold War, or the middle of the
Cold War, he is being taught like the most controversial, you know, dangerous ideas of the literal
enemy in this college environment.
So you might go, what does a fighter pilot possibly need to learn this stuff from?
Well, when he gets shot down over Hanoi and he gets, or over North Vietnam and gets sent
to what's called the Hanoi Hilton, one of the worst prison camps in maybe the 20th century,
you know, we're talking like Auschwitzbad level of torture and just one of the worst things
that humans have subjected other humans to.
there in a North Vietnamese Marxist prison camp,
suddenly the ideas that he was taught
actually operate as a sort of a line of defense
because he's able to debate and argue
with his captors about what he's being subjected to.
And it's not just a prison camp,
but is a re-education camp.
But he already knows the stuff.
And so this is a famous story
because he talks about how this is why you can't be afraid of ideas and you have to be engaged with them.
So anyways, I was planning on talking about this regardless. And then I find out a few weeks before
that the Naval Academy at Orders of the President and the Secretary of Defense had removed about
300 books from the library on campus because they were like too woke or DEI focused or something.
It was just, it's your classic sort of authoritarian playbook of like, we tell you what you can see
and we're going to make a show of certain ideas being accessible.
And so anyways, I was going to talk about that.
I own a bookstore for Christ's sake.
I don't think book banning is good.
So I was going to mention that.
And in fact, actually, the window of my bookstore is a quote from Rage Against the Machine
that says they don't got to burn the books.
They just remove them.
Right?
We tend to think of it as like, oh, the bonfire of the vanities.
But no, they just make it a little harder to get.
So I felt I couldn't not talk about this.
And then, you know, they canceled the two.
talk about an hour before I was supposed to go. I flew to Maryland. I was prepped. I was about to walk
over there. Hey, you know, the powers that be, we'd love to have you talk, but you got to remove this
section. And I said, you know, you know, I can't do that. And they were like, okay, well, then you
can't step on campus. And I was supposed to talk to the football team later that day. I was supposed to
give another lecture later in the year. It wasn't like, we'll kill your family if you do this,
but it was the choice between access.
Like I could have removed it and no one would know.
And I could have continued my access.
I could have all, but that's not what this is about.
And certainly not what wisdom is about.
And so like that's what I mean.
We all have our individual choices.
And then you've got to make the right choice,
the part of the choice that's up to you when it comes your way.
I love that.
I'm so happy that you get to tell that story in a way where, you know,
you stood for something.
Well, thank you.
I mean, I did try to tell them, like, hey, you understand this will get more attention than if you just let me.
A thousand people will hear me say this.
Millions of people will hear me if you don't let me say it.
But, and I think quite reasonably, nobody wants to be the person that ultimately the wrath of the president comes down to.
And those people had to choose between, like this guy's supposed to throw away his pension.
that he earned for 40 years.
You let Ryan Holiday say what?
Exactly.
You let him challenge the administration on the books?
You let them embarrass the president at the or the Secretary of Defense and stage in the Naval Academy.
I get that.
I mean, that's not the choice they should make.
It's also not a choice they should have to make.
The person I'm most disappointed with is not the president or the Secretary of Defense,
but the three-star admiral who is in charge of the Naval Academy.
me whose job it is to teach these kids how to make hard, right decisions, who just threw out
all credibility when they allowed those books to be removed from the, like, that is an order
that you say, sure, but it's accompanied by my resignation.
Yeah, right.
Right.
And the irony, and I think the ultimate lesson in all this is like, do you know what happened
to her?
they fired her anyway afterwards because she's a female admiral running the naval academy
and that was always going to happen.
And so often you think I'm present, and I've made this mistake in my own life and it's
most of the embarrassing moments in my career, the things I wish I could get back,
are any time I made the expedient choice.
And I said, well, I'll lose my job if I do this.
You shouldn't want to keep a job that you could lose by doing the right thing.
That doesn't make the decision easier and it doesn't make it any more or less fair.
But like anytime I've done that, where I've got, well, they're paying me a lot.
You know, or like, oh, I don't want to have to tell them that I think what they're doing is bad or whatever.
That's the, those are the ones you wish you could get back.
Well done.
I called my mentor after I got my first job in pro sport.
That was excited, you know.
And he said, he says, you sound excited.
And I said, yeah.
I was trying to play it a little cool because he's been around a long time.
He said, call me this excited when you've been fired three times because you stood for something.
Yeah, that's great.
It was a great gem that he passed on to me.
No, what a gift that like, hey, your job is to stand for something.
Your job is not to keep your job.
That's right.
Yeah, stand for something.
Very cool, man.
Thank you.
Brother, I appreciate you.
Thank you for adding good to the world.
Thanks for having me.
Yeah.
Open invitation, of course, always.
I won't take you up on it.
Yeah.
Awesome.
Thank you so much, Ryan.
Sweet.
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