Video summary
In this discussion, Ryan Holiday reflects on recent live shows and a challenging speaking engagement in Kentucky where he was forced to deliver his talk without slides due to last-minute logistical failures. He uses these anecdotes to illustrate that life rarely adheres to one's plans or rules; when external circumstances force an individual to adapt—such as performing with no notes or navigating technical difficulties—they often discover they are more resilient than anticipated. Holiday contrasts this artificial self-imposed challenge with real-life unpredictability, noting that while the band played Iron Maiden’s "2 Minutes to Midnight" before he could present his slides, the core lesson remains: relying on a specific way for things to go creates vulnerability, whereas being effective regardless of conditions fosters true resilience and adaptability. The conversation shifts significantly when Holiday recounts an incident at the U.S. Naval Academy involving Pleb Summer lectures on the cardinal virtues—courage, discipline, justice, and wisdom. He was instructed by academy leadership not to discuss a specific topic regarding the removal of books from the library as part of executive orders addressing DEI themes. Although he felt duty-bound to address the censorship of works like Maya Angelou’s memoirs and other titles dealing with minorities who served in the troops or died in the Holocaust, complying would have compromised his ability to teach courage and ethics to future officers entrusted with nuclear weapons. Holiday argues that true leadership requires independent thinkers capable of questioning orders rather than blindly following them, a principle exemplified by Admiral James Stockdale, a graduate of the academy known for practicing Stoicism while enduring torture in North Vietnam. Holiday explores the nature of wisdom as an elusive virtue distinct from raw intelligence or "compute power," defining it instead as a loop of learning, applying knowledge through experience, and repeating that cycle. He warns against seeking shortcuts to wisdom, such as relying on gurus or artificial intelligence without possessing the foundational understanding to verify their outputs. Using stories like Seneca’s wealthy Roman who pretended to be knowledgeable by whispering answers from literate slaves at dinner parties until a wrestler challenged him physically, Holiday emphasizes that true wisdom requires personal accumulation of knowledge and experience rather than mere appearance. He also highlights John Wheeler's concept that as the island of knowledge grows, so does the shoreline of ignorance, suggesting that genuine wisdom involves humility and an awareness of how much more there is to learn. The dialogue identifies several pitfalls where smart people become stupid, primarily centering on ego, a lack of empathy, and unaddressed childhood issues. Holiday cites Socrates' observation that no one errs intentionally; rather, people act based on their own limited perspectives or incentives, which requires the "negative capability" to hold contradictory ideas simultaneously without immediate judgment. He uses Temple Grandin’s work with cattle—where she realized a hose looked like a snake in black and white—to illustrate how empathy allows leaders to understand others' viewpoints before making decisions that could lead to disaster. Furthermore, he discusses the dangers of cognitive dissonance where success breeds overconfidence, causing individuals to ignore valid feedback or repeat past mistakes under new circumstances, effectively "multiplying by zero" in their personal lives despite high professional achievements. Ultimately, Holiday concludes that wisdom is not a static state but an active practice involving emotional work and self-awareness to prevent catastrophic failures later in life. He draws parallels between managing calories versus expending them on exercise and the necessity of repairing ruptures in relationships before they become irreparable debts. The discussion underscores that while intelligence can be innate, wisdom must be cultivated through confronting discomfort, engaging with opposing ideas, and avoiding the trap of thinking one's own view is universally correct. By recognizing patterns in history where great figures fell due to hubris or a lack of empathy, individuals can learn from low-stakes experiences rather than waiting for life-altering catastrophes to teach them necessary lessons about humility, adaptability, and the enduring nature of suffering as expressed by the phrase "this too shall pass."
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How did the live shows go? The last time
we were talking, oh,
>> we were discussing upcoming live shows.
>> Yeah, I think it was I was doing two in
Australia and you gave me this advice.
You were like, well, you told me that
you done it with no notes. And uh
usually like when you do talks at events
like they they don't want you to just go
up and give a speech. They want like a
presentation, but these were this was
different. So yeah, I had to figure out
how to do it with no no notes, which was
um it was like it I it's good to pick
arbitrary challenges and take something
that you're good at that you've done a
lot of times and just figure out a way
to do it the hard way.
>> Yeah. What's new?
>> Yeah. And so I had to sort of reinvent
it from scratch. It was challenging but
good. It's it's actually funny in Mark's
relitations. He talks about practicing
holding the res with your non-dominant
hand. Mhm.
>> And so just like what what's the way
that you're comfortable doing it? What's
the way you normally do it? And then how
do you force yourself to do it not the
way that you like to do it?
>> And to force yourself to do it in front
of the way you're not comfortable doing
it in front of 2,000 people audience
>> is a is a you know, it's a whole thing.
>> Difficulty plus. Yeah.
>> Yeah. I've always thought about doing a
a podcast episode with a guest that
somebody had organized for me. Yes.
>> And sat down opposite me and I didn't
know who it was. Yes. And I had to try
and do an episode without breaking the
fourth wall that I didn't know who they
were and see if I could excavate what
the [ __ ] is going on here. Who is this
psychologist,
athlete, coach, trainer, like what the
[ __ ] are I? And uh and do it without
like destroying the episode. I always
thought that would be like a fun
challenge.
>> Well, and and the reason you challenge
yourself artificially is that life
doesn't really care about your plans.
>> Doesn't play by your rules. So, I I had
a talk I was supposed to do in Kentucky
like a couple weeks ago. And so, I was
supposed to fly in uh I had all day and
then I would do the talk at night. And
then, you know, I get to the airport at
9:00 and it's like 30 minutes delayed,
30 minutes delayed, 30 minutes. It's
starting to get crazy and some
incredibly complicated, very expensive
travel adjustments later. I land and I'm
in the car. Like, it I'm already late.
So, they've pushed it. They've they've
been stalling. Everyone's there.
everyone's there and I'm the last
speaker and uh I'm I'm you know I'm
texting them and and I go okay like I
just landed uh I'm I'm 12 minutes away I
will be there uh I will run up and go
and and they they go okay that's awesome
we're waiting for you where are your
slides and I go what do you mean like I
I know for a fact they came in yesterday
um so you should definitely have them
but I'm like here they are again I'm
like texting here here's the link to the
here's the dropout links to the slides
And they're like, "Okay, awesome." And
then uh so, you know, they I get there.
>> 7 minutes to go.
>> Yeah. Seven. They I open the door, the
car, and I'm, you know, running
upstairs. I'm carrying my suitcase up up
to the thing. I'm getting there and and
then as they're ming me up, they go,
"And you don't have slides, right?" It's
like, "Is no one talking to each other?"
But like like now I know for a fact that
you've had the slides for at least seven
minutes, you know? Uh so so uh and and
there's like a band on stage performing
uh uh that's stalling because it's like
a
loop and the guy goes okay so um
>> uh the band's going to play the first 20
seconds of 2 Minutes to Midnight by Iron
Maiden and then you're up and I go
>> okay so we got that like we had a live
band performing uh like a song that I
like but no slides and then the guy's
like I'll try to figure out the slides
and I go in the next 20 seconds. What
are you talking about? I was like this
is, you know, this is done, man. Uh I I
was like, I'll just, you know, but I
walk and so I start to talk and I'm, you
know, now I've got, you know, 45 minutes
of time to fill with no slides
>> and you can't just do the talk you were
going to give without slides because
it's you can't be like normally there'd
be a slide
>> every other minute.
>> Yeah. Exactly. And so I'm like, what am
I going to talk about for 45 minutes?
I'm starting and then the guy's like
trying to talk to me via the screen, you
know? He's like slides comfort. He's
like slides slides incoming should be
about 10 minutes, you know, and it's
like this this is too late, man. Um but
but uh you know, I was able to just give
some version of the talk that I've now
given several times.
>> But maybe some new [ __ ] came out.
>> Yeah, of course. But but but the
interesting thing is like you think to
me the lesson in these things is always
like you think you need it to go a
certain way. you think you want it to go
a certain way and then when you were
forced to do it the way that you
didn't want to do it, not only do you
find something out about yourself, but
but you you actually find that the thing
you were preparing not to for it not to
happen actually isn't that bad and it
might be better in some ways. So, you
know, but like you
>> technical difficulties are a part of any
industry in life. And so if you if you
if you if you need it to go a certain
way, you're very vulnerable. If you're
good with it going effectively anyway,
>> Mhm.
>> then you'll be all right.
>> Yeah. What happened with that naval
academy
>> speech? There's a slightly different
technical difficulties. So, you know,
normally you send your like, so for the
last four years, I've been speaking
every year to the incoming class of the
Naval Academy. It's called Pleb Summer.
Um, so these are like the brightest kids
in the country, future naval officers.
So, they're going to run submarines and
fly F-16s and command aircraft carriers.
I mean, uh, future presidents, future
admirals, future heads of the CIA,
>> top gunship. These are the these are the
best you know most promising people in
the world actually because the naval
academy sometimes has like students from
other countries on these sort of guest
programs. So uh every season every year
for the last four years I've been doing
this series of lectures on the cardinal
virtues courage discipline justice
wisdom. So I've done courage done
discipline I've done justice and then I
was supposed to do wisdom this year. And
um so you send your slides in before not
for approval but for technical reasons
like you don't you don't show up with
your computer
>> because you know they don't have the
plug. You send them in advance. Uh so I
sent them in you know the night before
um as I had for every subsequent talk
and have had previously received zero
notes because that's not what we were
doing. And then I get a call, you know,
I get up, I go for a run, I'm walking
through the talk and I get a call from
someone at the academy and they go,
"Hey, so there's this thing in the talk
that we would like you not to talk
about." And of course, I knew exactly
what they were referring to because I
had spent a lot of time thinking about
what I was going to talk about. Um, and
one of the things I felt sort of duty
bound to address was they had just
removed several hundred titles from the
Naval Academy library. Um, as part of
this order from the president that was
supposedly about addressing,
you know, DEI and wokeness or whatever,
they had removed books that talked about
those themes from the library. Okay? So,
you could say you have a problem with
the policies, right? and the president
is allowed to decide, you know, how the
academy is going to be run.
>> But you can't remove books from an elite
university because you don't like what's
in the books. That's a very different
thing.
>> Well, there's an interesting point
there. Was it uh Megan Phelps Roper that
did the witch trials of JK Rowling? So,
this was the inverse of that situation
that was uh one book or one series of
books, Harry Potter. Yeah. uh originally
in the 90s and 2000s by right-wing
fundamentalist Christians. They
campaigned to have them banned from
schools because they were worried that
it was rich witchcraft. And then two
decades later,
>> the left-wing progressive people are
trying to get it banned because they
think that JK Rowling is a transphobe.
And what you're talking about here is
this is the other way round. This is
rightwing in the modern world trying to
get rid of books that they don't like.
Well, and and and this is why we don't
ban books because it's stupid and uh it
it it's incredibly inconsistent, right?
Like the Bible is a very banned book. Uh
so so they're they're removing it um
because these books have these
objectionable themes, but of course mine
comp is still in the pres is still in
the uh academy library. And you know, so
here you are removing a book that's
talking about like minorities that died
in the Holocaust or minorities that
served in the troop. Like when when you
when you have J chat GPT pull up a list
of books that it thinks might be
objectionable and then you just rip them
out of a library, you're in very
dangerous territory. And so I was going
to speak about this in in uh because it
pertains to something I've been writing
and talking about there which is that um
Admiral James Stockdale is one of the
most famous graduates of the academy,
one of the most famous modern
practitioners of Stoke philosophy. After
he graduates from the academy, the Navy
sends him to Stanford where he gets a a
postgrad degree and he studies quite a
bit of philosophy there. and his
favorite course while he's at Stanford,
this is in ' 62 or ' 63, is he takes a
course on Marxist thought and they only
read the primary Marxist texts. So, not
like commentary on Marx, not
neo-Marxism, but like Marx himself and
Lenon and they read and they they spend
an entire semester talking about what
the Marx Marxists thought. And you might
go, what does a Navy fighter pilot need
to learn about Marx? Well, when he ends
up in a Marxist prison camp in North
Vietnam, is subjected to years of
brainwashing and torture and propaganda.
It actually comes in extremely handy.
And he would talk about how he was able
to go back and forth with his captures
and that in many cases he knew Marxism
better than they did and that this was a
defense mechanism, right? And it's
actually funny as the Stoics talk about
this too, which of course I was going to
talk about in the talk. The Stoics
Senica talks about reading like a spy in
the enemy's camp. The idea is you want
to stop.
>> Oh, no. No. I just heard the song. Good.
Good. Um, so the the idea is that you
you want to know what your opponents
think. And in this case, we're not even
talking about opponents because we're
talking about, you know, the memoirs of
Maya Angelou that are getting removed
from the the the library of a again a
university on par with Harvard or Yale
or West Point. So I was going to talk
about why this is this is why we can't
be afraid of ideas and in fact we have
to engage with ideas that we disagree
with and dislike. Um
well you can imagine the people that are
removing well once the leadership of the
academy had put themselves in the
position of not challenging the order
and you know sort of removing the books
without protest. They're now in a tricky
situation of like can we allow criticism
of this decision? Right? This is what
happens when you and of course Stockdale
talks about this too. He talks about
when you start to make compromises with
extortionists. You have to make more and
more compromises and then pretty soon
you're not just removing one or two
books because it's controversial, but
then you're revoking invitations to
speak from people who are criticizing
that idea. Um, and it escalates. So, so
they they um they asked me to remove it.
And it's like I can't I I felt and I
don't know if I could have made this
decision early on in my life, but uh I
talked to these kids who are going to
again in the future be entrusted with
nuclear weapons and immensely powerful
bits of machinery and budgets of the
billions and billions of dollars
>> that I can't give them a lecture about
courage. I can't give them a lecture
about discipline. I can't give them a
lecture about ethics and doing the right
thing. And then when someone says, "Hey,
if you want to keep talking here, we'd
like you not to speak about the things
that we're trying to sweep under the
rug." And so I said, you know, I can't
do that. And so, of course, the
invitation was revoked and then so was
the subsequent invitation. Um, the
interesting thing about it to me was I I
said, you know, I think you think this
will
avoid controversy, but it's only going
to do the opposite. Not only is it going
to do the opposite because like this is
a public event like not this is a a a
publicized event that is now ended you
know 10 minutes before it's supposed to
go on but you know part of the like I
was speaking the I was speaking at was
brought there by this center on campus
called the Stockdale Center for Ethical
Leadership. So the irony of like let's
remove books that we find to be
objectionable and then let's not talk
about it and then let's pressure a
person from the center of ethical
leadership. You know the the ironyies
are stacking up here. But like there is
this there is this presumption that
people in the military are just like big
tough strong
you know uh robots that you send in to
do but that's that's what gets countries
and the world into trouble like the the
crown jewel of the American military uh
and the western militaries for centuries
has been the ability of their leaders to
think to uh challenge orders and to
question, right? This isn't to say that
it's anarchy, but like you need
independent thinkers or everyone's
thinking the same thing and thus not
thinking at all. And so like you are
going to want these young men and women
at some point when they're entrusted
with leadership and power to make
difficult unpopular decisions that are,
you know, maybe not always in their the
interests of their careers and what this
leadership is showing them in this
moment is
uh we might say that but we don't mean
it.
>> Right? Like like imagine you become a
multi-star admiral of the Naval Academy,
one of the you know crown and then
you're not just a party to removing
books from the library but then you are
like what I guess this this is a theme
of that I've been writing about for
these last couple years is like what is
the point of power influence success a
platform if you don't use it?
>> Mhm. And so it was a it was it was a
strange surreal experience that's only
sort of gotten worse. Like the West
Point just revoked an invitation uh and
an award they were going to give to Tom
to Tom Hanks this week um because of his
political views. So we are in this full
sway of like the pendulum of cancel
culture snowflakeism has gone from like
this way to this way.
>> Mhm. And it's the same thing that's
happening just in the opposite
direction.
>> Yeah. And it's equally stupid in both
directions and it doesn't help anyone.
Um, and then you know it was funny
because people kept going like well what
about this book and what about this
book? You know this is a bad and I go I
don't know the names of basically any of
the books. Like I don't give a [ __ ] what
the names of the books are. I'm actually
sure most of the books are bad. Like the
the library has hundreds of thousands of
titles. it would make sense that in fact
a large percentage of them are I I would
agree that most books that are published
are bad and stupid and wrong like uh
that's that's how it works but but a
free society you know uh requires the
free transmission and publication of
ideas right and so it's a it's a weird
it's a weird moment in time to be sure
>> you've been in the war zone it seems
>> well no as I maybe maybe an intellectual
war zone. The I think what's ironic
about it is these are people who are
going to at someday be sent into a real
war zone
>> and we're nervous that they're going to
read Maya Angelou or even the most like
offensive, stupid, wrong, you know, ass
backwards book and just be like
>> immediately.
Yeah. Their mind melts like actually
this is when we would want to find that
out, you know.
>> H okay. So read these read these stupid
books. See if your mind is changed and
if so out you go.
>> Yes. Exactly.
>> You say wisdom is the most elusive of
the virtues.
>> It's the hardest to define. I think
courage is something we know it when we
see it. You know, discipline pretty
straightforward. I think the thing about
wisdom is that um
it it's it's not just elusive in terms
of its ineffibility. Like it's hard to
define. um you know it's it's
experience, it's knowledge, it's
intelligence, it's creativity, it's
insight, uh it's perspective, it's it's
all these things, right? But the
interesting thing about wisdom is that
it's one of those ones that if you think
you have it, you almost certainly don't.
And the second you think you have it, uh
you find that there is more left for you
to learn. So there's something elusive
about it in the sense that the horizon
is elusive, right? Like you approach it
and you feel like you're not making
progress. You look behind you and you
clearly have made a lot of progress.
Look at all the things that you've read.
Look at all the things that you've
learned. Look at how much smarter you
are than you were before and look how
far away the people who were standing
with you when you began are. But but
there remains an infinite amount
>> still to know. And so there is something
>> inherently humbling about it. the the
physicist John Wheeler said, you know,
as the island of knowledge grows, so
does the shoreline of ignorance. I think
that's that is the paradox of wisdom
that the the more you learn, not just
are you humbled, uh, in that most, you
know, really smart people are actually
quite humble. Um, but but the more you
learn, the more you learn about all the
things that you still want to learn
about. M what do most people get wrong
when they think about wisdom where it
comes from?
>> Well,
you know, like there's some, you know,
um is it is it is it like book smarts or
street smarts? Like is it school or is
it life? As if it's this binary thing.
And of course, it's a combination of all
of the above. It's like you want a base
of of knowledge. Ideally, uh you want to
learn from all of the experiences, all
the the the great ideas that humanity
has come up with over thousands of
years. And then you have to go out and
experience things and then what that
does is it informs what you've learned
and then the things that you continue to
learn inform the experiences you're
having. So the subtitle of the book is
like learn, apply, repeat. And that's
the idea is that is that it's this loop
of always be learning, always be
exposing yourself to things and then
always
be going out and applying and trying the
ideas. So, you know, if you're just sort
of reading up in your your tower, so to
speak, uh you might be getting smarter,
but I wouldn't say you're getting wiser.
Um and then there there is something
fundamentally stupid though about trying
to learn all these lessons yourself,
right? like um you go uh I think I think
it was Otto von Bismar you know he said
uh any fool can learn by experience I
prefer to learn from the experiences of
others. So
why why would you want to figure
something out when someone has been in
your exact position before and not just
uh learned from it but like written
about it and then other people have
written about them and and so you think
about like this position you're trying
this this thing you're going for this uh
thing you're attempting like some of the
smartest people who have ever lived have
have spent years of their life thinking
about just that thing and then and then
there is the ego in us that goes like
well I'll wing it you know or or I I I
know better and and so the reason that
humility is this key to wisdom is not
just like you can't learn that which you
think you already know but but it it it
it keeps you hungry to learn more and
more.
>> I have this idea about unteable lessons.
Yeah.
>> And it's a unique category where no
matter how many songs and movies and
stories from your grandparents and
warnings,
>> you cannot expedite the process of
understanding this thing through
somebody else's story tale. You can only
learn these things. Money won't make you
happy. Fame won't fill your selfworth.
That girl's not lovable. She's just hot
and difficult to get. You should see
your parents more. You should work less
hard. you know, these things that are
cliche. And the reason that they're
cliche is that they seem to be
so reliably groundbreaking to everybody
when they arrive there. So, it almost
becomes its own. It's like a
self-defeating prophecy
>> that everybody says it, which means
everybody thinks that they know it,
which means everybody discounts it as
like, oh, that's just like a wives tale.
That's not like you shouldn't put your
hand on a hot stove. That's these
people. They've just accepted it as as
part of the source code of reality. But
I watch me dance through this minefield
and I'll do pirouetses and I'll spin
around. The rules won't apply to me. But
the funny thing about that is I think
one of the reasons those lessons are so
cliche and then why
uh you talk about them so much is partly
because
okay so you take something like money
won't make you happy or fa fame is empty
or you know you're not going to fill
that hole in your soul by achieving and
doing. Um, that's, you know, a theme in
literature and art and and of course
social psychology also. And and
there's probably some evolutionary
reasons why that's a hard lesson to
learn, right? This is what propels
humanity forward.
>> But some of us learn that lesson sooner
than others, right? Some people have to
go as far as Alexander, like literally
to the end of the worlds to learn it.
And then other people experience it
during their college graduation.
>> What was Alexander's realization around
that point?
>> Well, I'm just saying Alexander gets all
the way to the end of the world and and
his men are like, "How much longer are
we going to do this?" And he says, you
know, "Let it be said that you turned
around here and, you know, didn't
conquer the rest of the world with
Alexander." And then he subsequently
dies and he dies this brutal painful
death where some some of the theories
are like he he was like sort of in this
like conscious coma where he's like
frozen but like he it was a it was a
let's say it was an end where he might
have had a few moments to contemplate
whether it had all been worth it, right?
>> And so my my point is you can learn it
at the very far end of the extremes or
you can hear it at the first inkling of
it. Like I I I've said before, like I
feel like life is always trying to tell
us something and eventually it will tell
us in a way that we can hear it and so
>> the whispers just get louder.
>> Yeah. Do you want to hear it? Do you
want to hear it when when life is
whispering this to you or do you want
life to have to pin you down and scream
it in your face? You know, like in
sobriety circles they talk about like,
you know, hitting rock bottom while you
still have two cars in the garage. Like,
do you have to hit rock bottom when
you've blown up your entire life and
lost everything and everyone or can you
take this DUI as a sign? Right.
>> That's a really a really great point
that um yes, these lessons are
unteachable, but some people need to be
taught more times than others.
>> Yes. And and and that was, you know, the
Romans talked about, you know, the the
fool is not someone who who stubs their
toe on a rock. It's the person who stubs
their toe on the same rock more than
once. And so it's how quick can you
learn the lesson? And so part of part of
why you you take in especially early on
why these classic uh myths and ideas and
the western cannon is so important is
that they contain from the Bible to the
Odyssey uh you know to Marcus Aurelius
and Aristotle and and and all the great
stories is they contain kind of the sum
total of human wisdom
>> right and some of them though you don't
learn you you hear but you don't
understand until you have the experience
experience that matches that lesson.
>> Oh, that's thing.
>> Yes. And and so you need to you need to
you you need to have the ideas to match
with the experiences that neither is is
is
sufficient on its own. I love that that
blending of the two especially because
if you don't have a a good enough
framework sort of a robust scaffolding
to hold your life's experiences on yeah
maybe you will take the right lesson but
maybe you'll take the wrong one maybe
you get gold medalist syndrome you think
ah two yes
>> two that's the issue the issue is I need
to prove that I wasn't lucky that I was
good I don't just sell the one company
for $100 million I've got to run it back
again in a different industry And then
the thing as opposed to no this is
habituation. You have learned this
before. It's the exact same gremlin just
coming at you from a slightly more
conniving angle.
>> Yes. Um and and and it's to be able to
recognize, oh, this is what so and so
was doing here. This is so and so at
this, you know, critical juncture point
like and and and there was a time when
we had enough shared story. First off,
there were just fewer stories, so
everyone could kind of recognize, oh,
this is like, you know, Odysius at the
sirens or this is Hamlet or this this is
this is, you know, George Washington at
this moment. You know, you you have
these stories that are designed to teach
these moral lessons like the greatest
biographer of all time is Plutarch. And
Plutarch says, you know, there's a
difference between biography and lives.
And he says, I write lives. And lives
are illustrated by a certain anecdote, a
little story, a a an utterance of a few
words that help you unlock the lesson or
the the fatal flaw or the the the
brilliant genius of this person. M
>> and and so when you read about these
historical figures who are often flawed
and tragic figures, the idea is you take
back from them little lessons that then
yeah, when you're winning a gold medal
or you just sold a company or you know
you're you're about to gamble it all on
this thing that you believe is you know
the key to unlocking your happiness or
your legacy or whatever. you go, "Oh,
maybe I should ask myself, am I about to
do what they did?" And how did it go for
them? And and so it's having this broad
array of case studies and stories that
were,
>> you know, not always the most
historically accurate, but they were
illustrating something about the human
experience that we need to remember.
Mhm. I was spending time with an
impressionist a couple of weeks ago and
>> like a comedian.
>> Uh yeah. Yeah. Yeah. Or would you mean a
painter?
>> No. Sorry. Yeah. Good. Good. Good. He
does impressions. Whatever that person's
called, they both called the same thing.
>> I think so.
>> Someone should change it. Um anyway, and
I was explaining I've got Matthew
McConnA coming back on the show. That
wouldn't that be exciting?
>> And uh he's like, "What was it like to
sit down with him the first time?" And I
said,
>> "All of the thing, he's very charismatic
and all the rest of it." And he does a
great MCA. Uh, and I said, "He does this
thing that you didn't do when you did
it, and he doesn't ever have, it seems
to me like he doesn't have stuff in his
mouth, but he goes like,
he's sort of like as if there's a little
bit of straw or something that he needs
and he does this with his hand." And the
dude was like, "That's the unlock." And
he explained to me that in
>> the art of doing impressions of people,
>> uh, there is a uh, an unlock. And the
unlock is this one thing, the way that
you speak, the pronunciation of the S,
the uh moving of the fingers, the hands,
the face, whatever. He says that's the
thing that people hook on to in the same
way as what you're talking about here is
that there are these portable stories as
Clay Habit calls them, these individual,
maybe even a tiny little apher,
three-word apherism, whatever. Um, and
you go, that's the thing. And both me
and you uh quote other people a good bit
because
>> original thinking is pretty tough and
also people way smarter than me and you
have already figured stuff out and it's
kind of our job to
>> essentialize that and and and make it
accessible.
>> If I could say it better I would.
>> Yeah, true. And I've tried. Um, and I
think that, you know, in many ways, for
me, the reason that I love it is that,
um, using small quotes, apherisms,
mantras, stuff like that is kind of like
a windzip file that condenses down this
big thing. My memor is not that good,
but it's not bad if I just have to
remember this small sequence, and I go,
"Ah, yeah. Uh,
>> the universe has changed and life is but
what we deem it." Oh, well, there's like
this big thing that that means that I
kind of remember a bit.
>> Yes.
>> But I can recall this. I can remember
the chorus and from that kind of the
rest of the album comes along with it,
too.
>> Yeah. And and I think
too many people have confused,
you know, history and trivia. exactly
what year this happened, exactly how the
name is pronounced, you know, exactly,
you know, uh where the troops were
aligned in this battle or that battle.
Um, you know, is is much less important
as as to the the why or the characters
or the kind of the the fundamental moral
lessons uh that that that thing has the
opportunity to to teach us. And that's
what the classics and the sort of
ancient stories have always been. Like
Catis, do you know the story of Catis?
So Catis is this Roman general who's
living in retirement. This story will
will sound familiar to you in a second.
He's this famous Roman general living in
retirement. And the Roman army is in
battle in some distant land. And
basically the whole of the Roman army is
is uh is trapped. And so Rome is uh
basically undefended. And so the the
Roman elders go to Catis who is plowing
on his farm in retirement and say we we
need you to save Rome uh and we will
make you dictator. And so he's made
dictator. He leads a a small uh you know
troop of Roman uh Roman auxiliaries uh
and you know frees the Roman army, saves
Rome uh and is now dictator and he after
17 days resigns uh the dictatorship and
returns to his farm. Right? This is the
plot of Gladiator, of course. Uh, and
it's also the model for George
Washington resigning his commission
after the Revolutionary War. Um, you
know, uh, when King George hears that
that Washington is going to return to
his farm, he goes, "If he does that,
it'll be the greatest man in the world."
Both of them understand that this is an
illusion to the example of Catis. when
when Washington resigns the presidency
after two terms, it's again Catus that
he's so this is a famous story. Um but
Catis almost certainly did not exist.
Like that is a story that goes back so
far in Roman history that there is
almost no factual basis for it that
anyone can clearly point to one way or
another. But the story has existed for
so long that the Romans certainly
thought it was true and Washington
thought it was true and King George
thought it was true. And you know when I
tell it to my seven-year-old it may as
well be true. And I think some people
have taken the role of the historian to
prove that it didn't happen to be like
here George Washington didn't chop down
the cherry tree or you know Cincinnati
didn't really exist or this didn't
happen or it was more complicated than
that. Um, and look, if you're a grad
student specializing in that thing,
perhaps that is important. But for most
people most of the time the the
significance of that is the the lesson
of sort of restraint and selflessness
that that that actually power can be
laid down and that you know the truly
great and powerful people not only do do
that but that's the gift they are giving
the future generations this continuing
this tradition the peaceful transfer of
power and so the the History is supposed
to be the sort of sacred hardearned
knowledge uh that we pass on from person
to person. And so a lot of the famous
stories, you know, maybe they're true,
maybe they're not. If if you're being
literal about them, you're missing the
point. Did you read Derek Civ's book,
Useful, Not True? No. Okay. So, I had
this idea for I swear to God, I came up
with it independently, which was uh
figuratively true. Literally false.
>> Yes.
>> Literally true. Figuratively false. Yes.
And Derek came up with something that
was not too dissimilar, which is usually
a good idea. Like it's like, hey, two
people pointed at the same thing from
different angles. Like might be
something here.
>> Um, literally true,
>> figuratively false. uh you uh
determinism might be a way to look at
this that uh perhaps there is no free
will and the entire way that we move
through the world is predetermined by
the big bang and the dominoes just
falling falling falling. However,
functionally what would you do with
that?
>> It's [ __ ] useless. It makes me
nihilistic. It makes me feel like I I I
don't have any control of my future. Uh
something which is literally false but
functionally true. Um, in the, uh,
Middle East, in sort of medieval times,
pigs are morally dirty creatures.
They're no more or less moral than any
other other creature. But in a hot
climate, their flesh contains more
pathogens on average. So, not eating
them probably a pretty good idea.
Porcupines can throw their quills. No,
they can't. They can't [ __ ] throw
their quills. But if you treat it like
it can, you stay just a little bit
further clear and you're less likely to
get stung. So this idea that
holding modern stories to the standards
of objective rationality, where does it
appear on the spreadsheet? Please show
me how this comes into land. uh I think
for a lot it was a good solvent that was
supposed to kind of wash away a lot of
[ __ ] that existed because there was
stuff that was uh literally false
functionally false and that actually
needed to [ __ ] off. You know, there's an
expression that that traditions are
often solutions to problems that we've
forgotten about. And
this idea, there's kind of been this
fetishization these days of like
thinking from first principles, right?
And it this is important
>> going to arrive at it myself.
>> Yeah. I I think for myself, I'm I'm a
first principles thinker. I I
>> not one of the sheeple. I'm autonomous.
>> Yeah. I don't care about your precedent.
And you know, a lot of precedent is hard
one, right? and and maybe even why it
was hard one or how it was hard one you
are blowing past and you are ignoring
why it was set up this way in the first
place. And so not only is it exhausting
uh and unsustainable to to truly think
you know from first principles and
everything but yeah sometimes um things
are incidentally solving one problem and
also solving another problem or things
are variables are are hopelessly tied up
with each other. So you you you go,
"Hey, we don't need this. This is
stupid."
>> And you don't understand because you
don't have 20 years or 50 years or a
thousand years of experience in this
thing that actually this is a subpar
solution or inelegant solution to a very
complicated or or multifaceted thing.
And so there the arrogance I think that
again what wisdom is is this humility of
having done hard things before and
solved hard problems before and you go
oh okay it's it's probably not going to
be solved like this and this thing that
popped into my head that should
magically resolve all of this you know
uh is is naive like do you know the
story of the Gordian knot?
>> No. So that there's this uh knot that's
tied that is impossible to untie and
person after person uh goes to to untie
it and if you if you untie it you know
you become the king of this land and I
think it's Alexander comes and and um
you know he he he solves the Gordian
knot by chopping it in half with his
sword and on yes that's technically a
solution but it's also not a solution.
You haven't actually untied the knot. Um
and and so so there is this again this
sort of uh fetishizing of like these uh
complete solutions to things that hey
the people before were not idiots
>> and in fact they had a little more uh
humility than you did and understood
that there probably was not a solution
that that pleased everyone or or checked
every box. And so that's why this is
where it is and why, by the way, things
have remained relatively stable for a
long time. I think we're seeing this now
in politics, but also life where, okay,
if you're a Silicon Valley investor and
you invest $50,000 in a company, um,
okay, the downside of you being wrong is
that you lose $50,000, but the upside is
you might make $5 billion. So that's
great in this very specific domain that
you are in where you get access to lots
of early stage companies. You have a
large broad base of capital and you can
throw you can be wrong a lot to be right
one time. Well most of life is not like
that right and politics and life
geopolitics
are not like that.
>> You don't get to be wrong that much
before there's a catastrophic outcome.
>> Yes. Yes. Um and so a lot of the systems
that we have set up and a lot of the
procedures we have this is not just in
America but all over the world talking
about the UN or the EU or all these
different institutions
they are there not to create the easiest
most well functioning efficient machine
in the world. They're there to make sure
World War II doesn't happen. They're
there to make sure that a nuclear weapon
doesn't explode. they're, you know,
they're there to prevent uh an economic
meltdown, right? They're protecting
against downside, which unlike say
investing is not you lose the capital
that you put in. The downside is you
lose everything for everyone forever.
>> And so understanding what environment
you're in and the stakes. This is also,
I think, something that some really
smart people don't have. And in fact,
they've learned a lot of bad habits from
being the master of one domain. Like
some domain expertise is transferable
and a lot of it is not. And and the
wisdom is knowing what domain expertise
is transferable and what isn't. You
write fantastic songs, wonderful
lyricist, great at melodies. Yeah. don't
care what you think about climate
change. Don't care what you think about
the Ukraine. Don't care like you're that
is not an area that your expertise can
go to. Now you can outsource that to
other people or you can become an expert
in your own right. Yeah.
>> But just because you're great at this
one thing.
>> Yes.
>> So I I agree but as with most things uh
the devil is in the details here. So for
instance
there are people from outside of an
industry. Yes. that get a new
perspective because of the fact that
they're alien to this thing because they
see something with a fresh set of eyes
that nobody else would. And the Wright
brothers kind of strike me as a pretty
canonical example of someone like this.
So I think balancing this
Chesterton's fence pilled let's be
careful with what we get rid of you know
which is a much more sort of
conservative less innovative let's move
fast break things position
>> with well you know sometimes we need
like a great man or great woman to come
and kind of do a thing and uh balancing
those two the innovation desire with the
iteration desire but but what you find
in the best of those people the Wright
brothers being a classic example of this
is there wasn't
this sense that everyone else trying to
uh tackle the flight problem and it was
a problem other people like people have
been interested in it for thousands of
years but you know like all the armies
of the world were also rushing to try to
figure this out at the same time you
know there wasn't this sense that
everyone else is a [ __ ] and we're
geniuses what the Wright brothers had
was this curiosity this sort of openness
to how am I work? You know, they spend
hours and hours just studying how birds
uh, you know, fly. They had a scrainess
to them. They were outsiders. They were
independent. But, you know, the first
thing the Wright brothers do is write to
the Smithsonian for like every book ever
published on flight. It wasn't a like
burn it all down, everyone's a [ __ ]
And in fact, they would have loved to
collaborate with the powers that be and
would have loved to be brought in uh as
part of it. So I there's this tendency
to celebrate the sort of brash, you
know, doineering
uh outsider who comes in and tears
everything apart. But I I think you tend
to find that the the most effective
reformers have a profound understanding
of why things are the way that they are.
So, so that is that's actually you know
the negative capability to go like
here's what I know and here's what I
think is true and here's what I
understand as an outsider and then here
I've done a profound deep dive as to why
it is this way like one of the most uh
profound like I'll give you two sort of
related reformers you have Abraham
Lincoln and then you have uh Thomas
Clarkson the two basically forerunners
of of the the abolitionist movement
Thomas Clarkson in the UK uh leads to
the the the eradication of the slave
trade and then slavery in England and
then then uh Abraham Lincoln ends it in
the United States. Both of them start
their campaigns against slavery. They
had this as as outsiders or as just
human beings this immediate impulse that
slavery is wrong that that it doesn't
matter that we've been doing it for
thousands of years. It doesn't matter
that you know billions of dollars are
riding on it. Doesn't matter that all
the religious teachers say it's okay.
None of that matters. They understood it
was wrong. That's your classic sort of
outsider view seeing the world from a
new perspective. But then what they both
do is they go, I got to figure this out.
Like Abraham Lincoln goes to the state
house library in Illinois and then the
library of congress when he's a
congressman and he goes and he actually
reads like what the founders said about
slavery and he realizes that the sort of
dominant view at this time that the
founders were out to preserve and
protect slavery actually wasn't true.
Thomas Clarkson his genius is
>> he realizes that slavery is actually
just like bad as a business. It's like
he studies the insurance claims that
slave uh uh traders are making on the
the human cargo that they are
transporting. He's looking at the fact
that like 20% of the sailors are dying
on each voyage. He he's actually going
and looking at what a slave ship looks
like and then he draws this famous draw
diagram that like illustrates the
vividness of of what was an abstract
problem before. So the point is um it's
not that you have to absorb the the
dominant view or the status quo but you
have to understand the logic of why it
is that way. This is where justice and
wisdom are are interrelated virtues.
Like it's not just oh I have this
opinion. I'm morally correct so
therefore the world should agree. You
have to have this curiosity to go well
well these people probably aren't wrong
on purpose. So why do they think this?
what are the underlying conditions or
incentives that are making them think
this way? You know, Lincoln, a lot of
people have tried to go, well, you know,
Lincoln is equivocating on slavery
because, you know, he was so
understanding of the South. But, no,
that's what empathy is. He says, you
know, like we are just what they would
be. We are just they are just what we
would be in their in if we were in their
condition. Meaning, he's like, if you
were raised in the South and this is
what you were taught from day one, you
would think about it this way. And so
what what you have to have the negative
capability to understand and for people
who don't know that's a thing that Keats
talked about the ability to have
mutually exclusive ideas in your head at
the same time or contradictory ideas.
You have to be able to go here's what
they think and here's why they think it.
That's not going to change what I know
to be true or that's not going to change
the fact that that's still fundamentally
incorrect. But I have the ability to
understand why it is that way. And that
is usually a prerequisite to doing
anything about it or doing anything
about it effectively. Like Elon Musk is
right. The federal government is very
inefficient. uh and and he has a lot of
domain expertise in his specific areas,
but most people predicted Doge would
fail because it would run up into these
sort of longstanding
uh obstacles and difficulties that I
think he thought he could overwhelm with
sheer force. Do you know uh Sam Caucus
from Levels? You know Levels, it's like
a a glucose monitor thing.
>> Oh yeah, Levels.
>> So he was the founder of Levels. He is
now the CIO of the Treasury Department.
Yeah, I'm interviewing him on Thursday.
We got an episode with him on Thursday.
It's the first long form
conversation anybody from Doge has been
permitted to have and it's been like
it's okay to happen. And this is one of
the kind of the fundamental questions
which is how
tied up in bureaucratic red tape [ __ ]
is the inside of the government when it
comes to trying to make things more
efficient and how much can you take the
Silicon Valley mindset of notion
templates and Slack and and if this then
that Zappia [ __ ] integrations. How
much can you Zapier integrate your way
through like vibe code? How much can you
vibe code?
>> Yeah. the government into efficiency.
Yeah. And how much of it is this oified
walnutshelved
mahogany leather [ __ ] Chesterfield
sofa [ __ ] that's getting in the way?
And I think that's going to be
>> and then and and then how much of it is
there
because that is the uh best solution to
an imperfect situation? And do you have
the humility and the openness uh and the
the uh empathy to understand that that's
uh why it is that way?
>> Does that suggest that
along with wisdom comes a um
humble compartment sort of gets brought
in for the ride as well that an amount
of humility uh grows with the more that
you are wise.
>> I think so. I think so. Um you know uh
Epictitus said one of the signs that
you're making progress in the path to
wisdom is that you get in fewer
arguments
>> and and I don't think that means that
you you know just roll over all the time
uh or that you you know you have no core
values. It's just you understand
well this is why they think what they
think. You know, as I get older, I have
I I certainly do have fewer opinions
about [ __ ] that I don't think actually
matters, right? I have I have fewer
opinions as I get older about other
people's opinions, right? Because uh
they're right. They like that, you know,
and I'm spending a lot of my energy
trying to explain why they shouldn't
like that as if it changes or means
anything. M
>> and so uh part part the stoicism was
this idea of getting to a smooth flow of
life. Right now you can get to a smooth
flow of life by uh removing yourself
from most of the contentious and
complicated parts of life. Right? Uh you
can have a smooth flow of life if you
live on an island in the middle of the
Pacific and you don't work, right? Like
you never have to worry about money.
You're not trying to do anything. You're
not trying to accomplish anything. You
don't care about anything. It's pretty
easy to live on vibes. Can you get to a
smooth flow of life in the arena, right,
as you're trying to accomplish and do
and contribute?
>> That's the same as you can do your live
talk with a fully scripted out comfort
monitor in front of you and slides
behind you.
>> Can you do it when there's no
presentation and you've just got off a
plane 12 minutes ago?
>> Well, you can have it. If if it always
goes that way, you'll be fine. But it's
not always going to go that the kind of
fragility of
>> that. Yes. And so resilience,
adaptability,
you know, being able to function and
contribute and perform is the ability to
to work in less than ideal environments
with less than ideal people.
>> Um and and that's a I think a skill you
cultivate and develop over time. Given
that we've got modern culture of
shortcuts, life hacks, how do you
convince people that uh wisdom is worth
a long uncomfortable
path? The thing is at at some point in
your life, you're going to need it,
right? You're going to come to some
vexing decision, some challenging
moment. You're going to go through
something. You're going to be in the
middle of something. And in that moment,
uh,
you're going to want to have wisdom to
draw on, right? Wisdom that needed to be
accumulated a long time ago. It will be
too late in that moment for you to do
the crash course to figure out all the
things that you need to do to develop
the meta skills you need to solve this
problem in front of you. Um, and so are
you doing the work now? To me, that's
the question. I I think one of the
things we can all agree about wisdom on
about wisdom is that it's not something
you're born with. There are certainly
people who are wiser than others,
>> but I don't think any of them came out
of the womb that way,
>> which is what distinguishes it from
something like raw intelligence. Yes.
Compute power.
>> Yeah. Wisdom is something you accumulate
over time. And so if you're going to
want to draw on it in the future, what
are the deposits you're making now? So
that that's the investment that you make
in wisdom. There's a story Senica tells
us and I think it goes to this very idea
of hacks and shortcuts and the the
fetishizing of of of like gurus and
teachers who can just tell you
everything you need to know. Watch this
video and you know it'll tell you
everything you need to know or you know
come to this seminar. Um he talks about
this this Roman who wanted to be seen as
smart. And so you know the Roman could
have
gone to classes, the Roman could have
read hundreds of books. The Roman could
have experienced things and instead this
guy uh acquires a a number of wealthy
slaves or sorry this wealthy Roman
acquires a number of very literate
slaves. Each one like an expert on a
different topic. And at dinner parties,
they would, you know, whisper in his ear
the things that he needs to know. And
so, everyone kind of thinks he's very
smart. And the guy thinks he's getting
away with it. He thinks he's figured out
this shortcut until
one of the men comes up to him and says,
you know, "Hey, this is a great party.
You're very, you know, love this
reparte." He says, "Have you ever
thought of of taking up wrestling,
competing in a wrestling competition?"
He goes, "Wrestling? I'm like an old
man. Why would I do that?" And he says,
"But look at how young your slaves are."
The point is like they can't do that for
you also. And and I think we we are
under the impression for instance that
like uh artificial intelligence is this
magical transformative thing because it
contains all this knowledge.
>> Um but but you still have to know what
questions to ask it. You still have to
be able to separate the good answers
from the hallucinated nonsensical
answers, right? It can tell you,
you know, oh yeah, that quote you're
talking about, it's in this book, but
you have to know what that quote is,
right? You have to know some
vaguely know what it is. And and you can
really only do that from the work. It
can help you solve some problems, but if
you can't recognize a good solution from
a bad solution or [ __ ] from from
from a real insight, it's not going to
do much for you. And I I I think people
think that people are always looking for
some magical thing that will exempt them
from having to do this really hard thing
>> and it almost never works.
>> Do you know that story about chauffeur
knowledge? Is this Richard Fineman maybe
or somebody else's famous physicist in
the 1900s and he was going around giving
the same lecture and over and over again
and his chauffeur uh was there at every
single lecture that he gave. Yeah. And
after a while, the chauffeur basically
knew the lecture off by heart. And he
said, "Hey, wouldn't it be funny if one
day we swapped and you went up and I'll
dress as the chauffeur and you'll come
in?" And this guy goes up and he gives
the lecture and it's perfect. The exact
same way that the guy that was supposed
to do it and somebody at the end asks a
question and says, "Excuse me, I I just
need to ask you." He says, "That is a
question that's far too difficult for
me. You're going to have to ask my
chauffeur." And turns to the chauffeur
that's the real guy.
>> Yeah. To know by heart is not to know.
Well, Naval Naval came on the show at
the start of the year and
>> just this lovely idea which is there's a
big difference between appearing wise
and being wise and the temptation to
wrote memorize things that give the
allure the illusion of wisdom like this
looks like being wise because it is an
insight that someone far smarter than me
came up with
>> uh the difference between being able to
put that out and that's not necessarily
a bad thing. Is that right? Okay, I I
understand and have retained the
concept. That's a very good first start
because without understanding it and
retaining it, write down, write down,
write down, uh you don't know it at all.
So, great first step. But what does it
mean to be able to explain it three
different ways? What does it mean to be
able to apply it in your life? What does
it mean to see that insight when you're
gripped by emotion?
>> Yes. Yeah.
to even recognize that there was a
kernel of insight or truth in the idea
is no is not nothing.
>> Uh but then yeah to really know it is
the next thing and this is where the
interplay between reading and study and
exposing yourself to ideas and then
having experiences is so important. And
it's also why it's a loop because
there are some things, you know, maybe
narrative non-fiction or whatever, um,
travel book or something. You read it
once and you're like, I get I get the
argument. I get I get what I'm supposed
to take from this. And then many of the
great texts, uh, literature, philosophy,
uh, plays, stories, poems, etc., You
have to read, have experiences, read
again, have experiences because um every
vantage point that you look at it from.
Uh particularly with the passage of time
allows you to unlock something new in
it. McConnA says when he's reading a
script that he reads it when he's tired,
when he's happy, when he's hung over,
and each time that he reads it because
you don't have the luxury of taking five
or 25 years to go back to [ __ ] crime
and punishment or whatever. Uh short
period. Okay. So, how can I change my
state so that that different perspective
that I'm coming in from, that different
vantage point, I get access to?
>> Yeah, that that makes a lot of sense.
The there are books that you there are
books you know people go oh I read that
and it there are books that are designed
for you to be reading it's not a thing
you have done it is a thing you are
doing
>> and
this was easier to do in the ancient
world because there were just fewer
texts you know there was fewer you know
you you might read the Odyssey 500 times
in the course of your life or hear it
exposed cuz there's not any other you
know major works to draw on. We have
this uh you know, we have all of human
history. We have thousands of years of
extra history and knowledge and art and
stories that that some of the ancients
didn't have. That's our our blessing and
our curse.
>> Well, I think that's a a a really
interesting challenge that we're facing.
A lot of the time, people may have
thought they knew who they were and in
the modern world have sort of lost
themselves. I I I had geographically
triangulated who I am and why I'm here
at this point.
>> And then they go through a period of
protracted challenge. Uh they lose a
thing, a person, a belief in themselves.
And now this sort of paradox of choice,
lots of options open in front of me,
plus this unmuring from who they thought
they were before,
>> uh, arrives them at a port that they
have no idea where the ships sailed to.
So, what do you think a wise stoic would
say about somebody who's lost themselves
in life?
>> Yeah, it's it when you when you lose
everything, there's something very
freeing about that. when all your
assumptions have been challenged or
turned over and there's something
profoundly destabilizing about it
because you don't you don't have
anything. So, I think you go
maybe one of the things you do is you go
back to those things that were formative
to you at one point. And I I've been
thinking a lot now about like what I'm
rereading, what I'm re-watching, what
I'm re-examining, because now that I am
different, now that I am in different
places, what I what I what strikes me
about them is so different. Uh, but
there is something
nostalgic and beautiful about going back
to something where you're like, well, I
knew who I was when I read The A Great
Gatsby for the first time because I was
17 and I know exactly what class I was
in and what I thought was important and
I can I can look here and see
>> what I marked. Like Joan Ddian has this
famous essay about journaling and she
says, you know, why did I record a
thought that I had at a train station in
Pennsylvania? Why did I write down this
thing that I overheard someone say in a
restaurant? Why did I write down this or
that? Why did I tell this story? And
she'd been journaling since she was 5
years old. Her mother gave her she told
her uh she told her mother she was bored
one day. And Joan Ddian's mother said,
"Well, here's a notebook. Why don't you
write a story and then you can have
something to read?" And so she'd been
taking notes for for her whole life. And
in this famous essay on notebook, she
says, "Well, why did I why why do I do
this? Is it a professional like rolodex?
is this like someday I'll find a story
to put this quote in. And then she said,
"No, that's that's it's got to be more
than that." She says, "Um, the purpose
of journaling is to keep on nodding
terms with who I used to be." She's
like, "That's what it is. It's to
remember to who it's it's to remember
who I used to be."
>> And there's something very powerful
about journaling. Like I have this
journal that I do every day where um it
has five lines on it. And you know, so
every 5 years I do a new one, but you
write like where you were on that day,
what you were doing, what you were
thinking about 5 years ago or that that
day and then you do it the next year and
the next year and the next year. And the
first year it's kind of cool and the
second year it's kind of cool. But by 3,
four and five, it's very powerful
because you're like, oh, you know, in
September of 2022, this is what I was
thinking about. And that feels very
urgent and important or that feels like
silly and weird. And and so her her
point was that that what journaling
allows us to do is not just write down
and record something, but it's almost
like um it's like taking a picture on
your phone and both cameras are working.
Like it's taking the picture of what
you're looking at and it's taking the
picture of you as you're looking at it.
And it it depends on which of those is
actually the more important image to
capture, right? M
>> and I what I think journaling as a
practice is very helpful to prevent some
of those dark nights of the soul. I
don't know who I am. I don't know what
any of this means. I don't know what
happened because you do know what
happened. You've been
monitoring it and tracking it
incrementally as you go. I wonder
whether the meta lesson as well is
nothing as is as important as you think
it is
>> apart from when you're thinking about it
like like that moment when you are
caught up in the rumination cycle the
worry the despair
>> the depression the anxiety the concern
uh and and although people unfortunately
don't tend to journal when this is
happening the elation the bravado the
overconfidence
>> yeah the ephemererality of all of it
like uh this is from Buddha Uh but but
this the story is you know uh the wisest
philosopher in the world was asked to
find a phrase that's true in any and
every situation and always has been and
always will be true
>> and what the answer that comes back is
and this too shall pass and and you know
that can be uh true of grief that can be
true of you know an incredible triumph
it can be true of despair it can be true
of happiness torture, all of it lasts uh
longer, lasts longer than you think it
does. And eventually it all does end
like it ends one way or another. The
Stoics say like like you're the Stoics
say like when you're feeling like
profound pain or like sickness or
whatever, you can say confidently to
yourself um this is going to end either
because it's going to kill you or it's
going to go away, right? and and um
sometimes it's only zooming out and
getting a little perspective on your own
life that you realize this is true and
then zooming out and looking at things
historically that you realize oh this
has always been true for every person
who has ever lived. I was reading
Unbroken
about Zampirini and uh I'd never read
that. So uh my favorite stories are kind
of solo or group people against the
odds. Endurance by Alfred Lansing uh
Forgotten Highlander by Alistister Urk.
Uh and Unbroken, Laura Hillbrand by
about Louis Zampirini. And uh I said
this to you last time, no one's done a
good Stockdale book yet, have they? I'm
in the works.
>> No way.
>> Mhm.
>> Let's [ __ ] go, dude.
>> I'm uh I'm maybe three chapters in. I
I've been
>> That's going to be the next one.
>> That's uh So, wisdom is this and then
that's that's the next one. I I
>> so perfect.
>> His story is [ __ ] incredible. Like so
much better than you would think it is.
Like I think people think Can we nerd
out about Stockdale?
>> Yeah. Yeah.
>> Okay. So, for people who don't know,
Stockdale shot down over North Vietnam.
and he spends basically seven years in
what's called the Hanoi Hilton where
he's tortured, spends the vast majority
of that time in solitary confinement.
Um, horrendously tortured. Okay. So, the
key to understand like it's not it's
it's actually a much more powerful story
than even Unbroken because um,
Zampirini, I think I'm saying that
right, is is your ordinary prisoner of
war, right? He is an enemy combatant
held against his will. Right?
>> So Stockdale is in effectively a
re-education prison. Right? Like that
the job is to to take these people to
break them and to turn them into
propaganda assets. Okay. But the thing
you need to know about Stockdale is
Stockdale is in the air the night of the
Gulf of Tonken incident. So Stockdale is
there at the beginning of the Vietnam
War, which has begun under effectively
false pretenses. So when he is shot down
uh several months later and he's he's
parachuting into this camp and he says
to himself, you know, I'm entering the
world of Epictitus, he's not just going
to be held captive and not seen his
family for, you know, however long. He
possesses
the most terrible secret that you could
possibly possess other than perhaps
knowing the nuclear codes or the you
know like there isn't a secret that his
capttors would have been more motivated
to know than to know that he was in the
air and watched them effectively. He
says we were shooting at ghosts that
there was nothing there that because the
the the North Vietnamese know that they
cannot win militarily. They have to win
in the court of global public opinion.
So imagine they were to come in
possession of a pilot who was there who
who saw his country do something wrong
and imagine they could flip this person.
So breaking isn't like, oh, hey, let me
tell you like how a US aircraft carrier
works or let me tell you like the secret
vulnerable spots on the F-16. He
possesses the most significant secret of
and and um
uh you know piece of information. So
like he has a very special sort of
artillery shell hidden inside of his
brain. Yeah. And that can be deployed by
people who would really like that
specific weapon. or just imagine the
moral weight of what he is dealing with.
So he's not it's not like he's um you
know flying over Nazi Germany and he
gets shot down and he's being held by
the worst people of all time. Uh he's
fighting he is he is he is not uh
fighting
it's a it's it's it's a morally
complicated world.
>> He doesn't have he doesn't have pure
virtue to stand on top of.
>> Yes. And he and so he has to bear the
weight of this. It's a flimsy position
to hold.
>> Yes. And so what is he what is he
holding on to? He's holding on to this
idea that he is his brother's keeper.
And that if he betrays his country, who
he's really betraying is the other 200
or so prisoners and then all the other
drafties and officers. He's betraying is
he's not worried about protecting Lynden
Johnson, right? He's worried about the
person in the cell next to him. And so
the the the the mental gymnastics and
the moral injury and weight that this
guy has is unfathomable if you think
about
>> Yeah. Whereas when you look when you
look at Alistister Urkart from the
Forgotten Highlander,
disentry for four years straight, forced
march, bridge over the river Quai, etc.,
etc., locked in a tin box, knocked off
his feet by the bomb blast from
Nagasaki. Hardcore [ __ ] That's like the
equivalent of just climbing Mount
Everest, which is just you versus the
elements, you versus the the
>> battle of attrition that's on this sort
of one plane of existence. What you're
saying that Stockdale had was this like
astral
>> Yes.
>> karmic challenge that he's also fighting
with.
>> Yeah. And and so far I've been
fascinated by his childhood. And then
when he's at the Naval Academy, and this
is what I've been nurturing out about.
So when he's at the Naval Academy,
when he's a senior, the first uh the the
man, his name is Wes Brown, who would go
on to be the first black graduate of the
Naval Academy, is also there. So he's
the Jackie Robinson effectively of the
Navy.
>> And so as Stockdale is this young
student who's just trying to get ahead,
he's watching this other guy go through
this, you know, horrendous ordeal. like
they he had to have like basically
guards on him because they were worried
other midshipman might kill him. Uh and
he there was a a sustained campaign to
give this guy West Brown Demerit so he'd
get kicked out of the academy so they
wouldn't have to graduate him and then
he wouldn't become a naval officer.
There only been like 10 naval officers
in history, black officers in history
before this happened. So he's watching
another person go through effectively
what he has to go through 20 years
later. A sustained campaign to break you
as a person and crush your soul. Right?
That's what the the the
capttors in the prison are not just
trying to go, hey, if we don't give them
food and water,
>> you know, will they turn on their
country? They're trying to break them as
human beings.
um you know uh they're torturing them,
they're playing mind games on and his
famous thing Stockdale is
uh
tortured for days on end. And then they
basically in a moment they switch and
they go, "Okay, uh it's too much. We we
pushed you too far. We're sorry. Why
don't you go uh to the bathroom, clean
yourself up, you can go back to
yourself."
And he realizes that they would never
give him anything for free. They would
never be nice to him for any reason. And
so he realizes, oh, there must be a
reason they want to clean me up. And he
realizes they're about to to parade him
in front of the cameras. They want him
to give a videotaped statement. Maybe
they maybe he's even sensing in this
moment that they know what he knows.
>> And so at this moment, he walks into the
bathroom. He says he knew he had about a
minute in there. And he begins to beat
his face to a bloody pulp uh with the
stool. And then he cuts he shatters the
mirror and he he basically scalps
himself like he cuts he gives himself
what he calls a reverse mohawk. He just
takes this jagged head and he cuts it
off the back of his head. He basically
makes himself um uh
>> unspeakable. Yeah. He's bleeding
everywhere and and it's like they come
in and they think he's trying to kill
himself and he hasn't. He's just
>> just maimed himself. So he is
unfilmable.
>> Not pressy.
>> Yeah. and and they go, you know, you
know, what are we supposed to do? We
were supposed to take you downtown. And
and he goes, you tell the major that the
commander won't be going downtown. And
and so he has this, you know, sort of
this like
this determination and this grit and
this in intensity
>> that takes on a whole different color
when you realize what he's holding and
what he's been through. and that that he
realizes that
yeah it it's about his connection to
these other people which I think is
interesting what I'm you find these
threads you go oh this is something that
you believe at 38 or however he's in his
late 30s when he's in this camp now he's
a commander that he fundamentally didn't
believe when he was 20 at the Naval
Academy he doesn't participate in the
hazing of this of this guy Wes Brown but
like famously Jimmy Carter who's like
from the deep south is in their class
and Jimmy Carter runs cross country with
them and Jimmy Carter is famously like
this supporter a guy who grows up in
like the segregated South is there
helping and encouraging this guy and and
Stockdale's like sort of too busy doing
his own thing
>> and so I'm I'm fascinated how does this
person go from like selfish in the way
that when we're young we're all I'm into
me and my thing and what I'm trying to
do I don't do you love I don't have time
for this other stuff you know like that
if not if I am not for me who is
>> mh
>> and then he becomes by the end if I am
only for me who am I and that's the arc
of stock that's
>> I cannot wait for you to do that
>> I I'm loving it
>> that's it that's sick and I guess
conspiracy tracking a story but it's
over like a tighter timeline right but a
lot of investigation what's going on but
this is like archive [ __ ] this is
>> well yeah to to go to what we started
with like uh the reason I'm doing the
book is because I have never done a book
like this and I wanted I love those kind
of books. So like the book could come
out and sell zero copies. The book could
come out and everyone could say that I
>> I suck and I failed at it. But I have
learned a lot. Like I have I have gotten
better at what I actually do in
struggling to do this thing which is not
what I normally do. I I want to bring up
a video of yours that I remember seeing.
I want to say,
did you video yourself getting the call
from your publisher about the New York
Times list of the last book or the one
before?
>> I think I've done it a couple times. I
know when the call's coming in, on the
camera.
>> Yeah, there there's there's this video
maybe maybe your kids in the room or
maybe not. Anyway, and you're you're
there and you're talking to them and
they say, "Ryan, just congratulations
bestseller. You came in at number
whatever the fuck." and uh you
say thank you very much that's good and
then basically but now I must get back
to writing the next book and I remember
I remember watching that and you know
we've met this is episode like seven
first time we come on the show was like
[ __ ] six seven years ago or something
yeah forever ago like when I was still
in
>> Oh this is sick I thought you were
saying I was on sick I
>> um so I've got like a you know good
understanding of sort of
>> I think where you're at I wanted to ask
you about that because
>> that at least from the outside looks a
little bit like somebody who is
struggling to take a moment to celebrate
their accomplishments because not and I
wouldn't I wouldn't say that it's as
uh
philosophically shallow as I'm just
moving on to the next thing. Yeah, I
don't think it's that. But I do wonder
whether there is a Puritan work ethic
driving you to the point where this
thing that happened that's great that by
all accounts I probably should put the
[ __ ] book down, get some cake and
allow my like put the put a couple of
banners up. I know they're [ __ ] Like
light some candles and and have a little
thing, have a little celebration. Is
that because I'm I'm very interested.
One of the criticisms typically of
stoicism is sort of a a a lack of
celebration of the good. This sort of um
indifference to emotion that is good in
times of strife, but kind of like having
sex with a condom on in times of, you
know, times of good. It's like a
prophylactic against everything,
unfortunately, including the
celebrations.
>> Um did you consider taking the condom
off at some point?
>> I there's a couple things there. I think
talking about wisdom, one of the things
you'll sometimes uh you can hear from
older people is like take the [ __ ]
compliment, you know, like like some
you're you're being like, "Oh, no, it
was nothing or I don't care." And
they're like, "No, no, I appreciated it.
You should take the compliment." And
that I think that's something that that
everyone should work on with if
someone's saying they like something, if
someone's saying good job, be gracious
with it because you think you're being
self- aacing, but actually you're
rejecting.
>> It's a middle finger to them.
>> Yes. Exactly. And and I I I think that's
something I' I've tried to work on. Some
people see that they go, "Okay, like so
you you hit number one, which I've been
lucky enough to do a couple times, and
and then you're just like right back to
work. Where's the joy? Where's the fun?"
Um, and my answer is is that the joy and
the fun is not in throwing a party for
hitting number one.
>> I like doing it. Like I like I like
writing books. It's like where I am
right now in the book that I am writing
is my absolute favorite place to be.
Like I I I'm not in the early phases of
like what is this? Is this anything? I'm
in the the the thick of like every day
there's like a challenging uh
invigorating uh problem to solve and
then I'm making progress on it and it's
coming together and I'm learning and I'm
growing and I'm I'm doing what I like am
meant to do.
So, um, one of the hardest parts of the
schedule that I am on is that usually my
my last project is coming out when I'm
in the my favorite part of the next
>> which is why you're so fired up about
Stockdale when we should be talking
about [ __ ] wisdom.
>> Yeah. Like I I didn't really do I I
maybe got like 45 minutes of writing
done today because I had a doctor's
appointment and then I'm here and then I
pick up my So like I'm actually not
doing the thing that I like to do. Um,
not that I don't like this. This is
amazing. But like I like doing the
thing. That's and and I I I think early
in my career I like all people I I I was
somewhat extrinsically motivated all
like I wanted to hit the best bestseller
list. I wanted you to say it was
amazing. I wanted recognition. I wanted
all that. And I I still do like those
things and I'm not shrugging them off as
nothing. It's just um I just feel like
the reward for succeeding should not be
taking away from like I'll tell you like
my first the first time I hit uh the New
York Times best uh Stillness is the K
Stillness is the key debuted number one
in 2019 and I remember I woke up I was
in LA on book tour and um I could I you
know my alarm goes off my phone and one
of my rules I don't check my phone the
first thing that I do when I wake up is
I I try to but That's difficult on the
road, right? Because
>> Yeah, exactly.
>> Your phone is the alarm.
>> And so, so it's like, you know, you pick
up your phone and you're like, "Some
stuff has happened, you know, like I can
tell some stuff has happened." And and
and I remember going um as I was staying
at the Los Angeles Athletic Club, which
is one of my favorite places to swim.
And I I go, "Okay, like this is either
good news or it's bad news about the
book cuz it's coming from New York,
right?" So, I'm on the West Coast.
>> Uh you're 3 hours behind.
>> Yeah. So, I I woke up and I was like,
"I'm going to go for a swim. I'm gonna
swim my exercise. I'm gonna do the thing
I love to do here.
>> And the news is the news. It's like, you
know, the cat in the box, right? It's
like I'm either a bestseller or I'm I'm
not.
>> Um I should get to enjoy the swim either
way.
>> And so I went I had this great swim and
then I checked in and I I you know was a
call from my agent and my publisher and
my wife and it was great. But like even
if it had been
>> Where the [ __ ] have you been? Uh I was I
I I was swimming uh front stroke.
>> In a way, the good news is just as much
a catastrophe as the bad news, right?
Like the the the good news if if I get
the good news and then I go swimming,
I'm just thinking about that the whole
time. Like pre presence is the gift.
Just being in the moment, enjoying the
thing is what you like.
>> I am going to interject that. I abhore
open loops. Okay.
>> [ __ ]
>> I am allergic.
>> You couldn't leave that.
>> I am allergic. Well,
>> I'm working on it and I know I know that
it's a I know that it's a a challenge of
mine that not knowing what's going on
with this thing to me is the sort of
[ __ ] that keeps me awake. The sort of
[ __ ] that wakes me up at 4 in the
morning. It's the sort of thing that
causes me to be thinking about that when
I should be thinking about whatever
else. Um,
I would struggle with that. And yet I
would say as well, I've seen other
videos like random [ __ ] that just pops
up from you that there was this video
where you complaining about trash.
Someone left loads of trash like near
the driveway to your ranch or something.
There was another one about fence posts
that might have even been like 5 years
ago. I do remember seeing some of these
different way markers and it's not a
representative.
>> It's what you've recorded and chosen to
put online that the algorithm's chosen
to give to me that I can remember.
There's a lot of filming here, but
>> I do get a sense of of like regulation.
>> Yeah.
>> From from seeing from seeing your stuff.
And there is something uh sort of
wonderful in the purity and the almost
complimentarily the boneheadedness, the
stubbornness, some might say, right? the
the the the yeah uh
single-mindedness of of some of these
approaches that
>> sure some days I'm only going to get 45
minutes in, but for the most part like
this is I am a writer. I am a thinker. I
am a musician and this is the main thing
and the main thing is for me to keep
that the main thing and I do find that
you know as a supported from the
sidelines of that stuff. It is good to
see somebody who I think at least from
the outside appears to be trying to find
that balance between I want to enjoy my
life. I I want to care for my family. I
don't want to sacrifice everything in
pursuit of the goal. But given that I
don't want to sacrifice everything and I
want to make a dent in the world, I have
to constrain the aperture of [ __ ] that I
do down to a really really really small
number of things. That's interesting. I
Yeah, there's a lot there. I I would say
regulation is the key to life, right?
Getting emotionally regulated. That's
what stoicism is. People think stoicism
is the eradication of emotions. It is
the regulation of de of emotions. It's
not having none. It's I'm feeling anger.
I am feeling frustration. I am feeling
envy. I am feeling worry. I'm feeling
anxiety. And I don't have to impulsively
act on that information. Right? And so
how do you find how do you build the
practice of like this is what I'm
feeling but this is what I'm going to do
right um a exercise a physical practice
is a great metaphor a training ground
for this because you're able to go like
I am feeling tired I am feeling not into
it I am feeling cold I am feeling
whatever and you're you're saying to
yourself but that doesn't [ __ ] matter
here's what you're going to do right and
so how do you practice
deciding who's in charge that's I think
really important and and it it's it's
something I think I've gotten better at
over time and you you you you work on
throughout your life. I think I know
that what I control is and what I enjoy
is the doing of the thing and I try to
think less about the things that are not
related to the doing of the thing. And
so, um writing is what I like. It's what
I enjoy. It's what I'm best at. That's
what I want to be doing. And then
publishing is the stuff that comes out
the other side. It's the it's the
byproduct of the discipline and
whatever. And so um that's that's kind
of how I think about it. Your point
about these open loops that I I think
that's a capacity you like again just
it's it's
>> it's a capacity you develop and increase
like hey I'm deciding I'm not going to
think about this until tomorrow or I am
going to be here for this school
performance. I'm gonna uh I'm gonna sit
here for this, you know, however long
this plane is delayed. I'm gonna I they
told me I'm not gonna get an answer back
on this medical test for two weeks.
>> I'm not going to waste two weeks feeling
shitty. And so, how how do you how do
you go I decide what I'm going to think
about? And to me that's a very stoic
practice like and it I think you you you
do it in the
in you you develop it intentionally over
often insignificant things so that in
the significant things you can you can
do it.
>> That's a good point. I mean the
the ability to learn how to get out of
quicksand is probably something that
both of us could work out in an
afternoon and we could practice it. If
you're trying to learn that while you're
in quicksand, that's going to be
significantly more difficult.
>> Also, quicksand doesn't exist, but it
basically a trope from westerns in the
50s.
>> I've been sighed by [ __ ] American TV.
>> Well, I mean, it it's one of those
things you're like, I got to be aware of
quicksand. It's like, have you ever
experienc You've been all over the
world. Have you ever seen Quicksand?
>> I haven't seen Quicksand, but I, you
know, I wasn't in America in the 50s, so
maybe that's it. I But yes, exactly. Do
you think intelligence then is overrated
when compared with equinimity?
>> Well, I think intelligence poised with
equinimity is a very powerful thing. And
there's a lot of intelligent people who
don't have it
>> and it prevents them from being as smart
as they can be. You know, Marcus
Aurelius's stepfather, the emperor
before him, Antonyinus, his last his his
final dying word is equinimatas or
equinimity. That's what he's trying to
pass to his uh to his son. It it's like
the most powerful thing that a leader, a
parent, a human being can have, right?
Is the ability to sort of be even to be
regulated. Again, this is easy to do
when the world is simple and things are
calm and nice, but that's not how it is,
right? So it's like like when you have
children especially like they can't be
regulated if you're not real regulated.
You see this if you have a dog, right?
You're like the dog is crazy because
you're crazy. The dog is responding to
your energy. And what is it can it can
sometimes be helpful to have something
as unbiased as that's why people love
ecquin therapy, right? Because you have
this creature which is really [ __ ]
sensitive. It it gets a little woo.
There's some stuff that I went to ecquin
therapy.
>> Uh the the lady that was there that was
really lovely was telling me about how
the horse heart has a magneettosphere
and it's able and I'm like this I'm
we're getting into some astral realm
[ __ ] here. But I do not deny prey animal
twitchy as [ __ ] If you have bad energy
it'll hurt you. You you you go oh okay.
And and then you yeah some of these
things can seem very woo and then you go
okay but I came into this this way and
now it's acting this way. There's
clearly been some kind of
>> litally false functionally true.
>> Yes. Yes.
>> Or maybe [ __ ] literally true,
functionally true. I
>> Yes. It it it exists. It doesn't It
obviously isn't real, but it's obviously
real.
>> You know what's another good example of
that is like a hot streak. Like
statistically, obviously it makes no
sense, but there is something about
being in in the zone, right? Um but
yeah, you you you go, "Oh, okay. It's
it's about how well can you how how good
are you at going from disregulated to
regulated. That's what stoicism is.
>> Well, I think a wonderful game for uh
couples to play uh is something like
when we get out of connection, the game
is how quickly can we get back into it.
Yes. And like what a wonderful goal for
you both cuz it's the dopamine. It's
this sort of cohesive we're working
together thing. It's a challenge. It's
not you against each other. It's you
against the problem.
>> Yeah. The third thing that is your
relationship and how quickly can we both
get back into that? Well, I'm going to
do the thing that I know brings you back
in and you're going to do the thing and
I that's something it feels like some
[ __ ] that Matthew's probably said. He
probably has at some point.
>> Have you had Dr. Becky on?
>> Dr. Becky?
>> Dr. Becky Kennedy?
>> No.
>> She's I know you don't have kids, but
it's the She's like the parenting guru
of our time. One of the the [ __ ]
greatest. She's like, don't try to be a
perfect parent.
try to get better at repair because
you're going to screw up. You're going
to get disregulated. You're going to get
it's about how quickly you can come back
and fix it.
>> [ __ ] director Becky stole my idea.
>> So, it's it's it's about that talking
about the intelligence equinimity thing.
And I I think you know a lot of very
intelligent people struggle to be
aquinamous. Yes.
>> And I I don't know whether a lot of
aquinomous people struggle to be
intelligent, but I think that one of the
things that people who have got sort of
deep in a piece
at least in my experience sometimes
struggle with is that sort of outward
drive to make a dent in the world and
that's fine because like you are your
own unit and who the [ __ ] is anyone to
say you're peaceful and largely content
>> but have you not considered making
yourself feel unworthy so that you can
go and you know write bestselling books
anyway um I guess another like an
interesting question with regards to the
wisdom thing is what are the mistakes
that otherwise smart people make
most often that stops them from becoming
wise. Basically, what is the
disadvantage that a person who is very
clever has of uh achieving wisdom? Are
there are there certain hurdles that
they need to overcome?
>> Well, I think we could say that there's
a number of things that really smart
people do that make them stupid, right?
Uh ego is obviously one of the the
things that makes us very dumb, right?
because it it it filters everything
through the lens of what we want to be
true or how we see ourselves, what our
identity is and not how things actually
are. So, ego obviously makes us uh
pretty stupid. Um obviously bad
information makes uh uh smart people
stupid. Um and of course ego contributes
to this. If you if you uh you know
crafted information diet that's about
confirming what you already think or
what you want to be true because you're
so fragile and it challenges your ego,
you're obviously going to get very
stupid. Um, I think we could say that,
um, you know, again, they seem to all
center around ego, but you know, stop
becoming complacent, ceasing to learn if
you're a know-it-all, right? You've
learned everything that it's possible
for you to know, right? Um,
>> that line that you've got about you
can't learn learn something you think
you already know.
>> Yes, that's that's Epictitus. Uh but I
think another way we get very stupid is
uh you you see people acting stupidly um
out out of a lack of empathy. Like Elon
said, you know, empathy is going to be
the death of western civilization.
Empathy is like the key to the greatest
uh achievements of western civilization
and and humanity. The ability to
strategically understand what is going
on over there. What do they think?
thought going back to Socrates. Socrates
said, you know, no one is wrong on
purpose, right? Going, oh, they've
thought themselves into this position.
They don't think they're being stupid.
They think they're being right. Um, you
know, Temple Grandon famously
watches this video. She gets called in
by these um by these uh cattle ranchers
who are trying to vaccinate their cows
against these different illnesses. And
they they put them through this shoot.
The cows are freaking out. They didn't
want to go in the shoot. They weren't
even being like killed or hurt. They
just didn't want to go in the shoot. and
they're, you know, forcing them and
forcing them and forcing them and she
with a black and white camera gets in
and takes pictures and the black and
white camera approximates how the cow is
seeing the world. She realizes that a
lot of these things um are seem scary to
a cat. Like a hose on the ground looks
like a snake in black and white. Or she
goes, "When you get down on the cattle
shoot, uh, this this chain that's
rattling against the gate sounds
incredibly loud and then it makes one
cow scared, which makes another c and
then that energy." So, so the ability to
get down and think about why someone
else is thinking about what is there's
this German word, which means like the
world view of someone else. What is it
like to be a bat? What's it like, you
know, what's it like to be my
eight-year-old? Because it's not the
same as how I can. So I'm going like do
this, you have to do this. But that's
from my view of 30, you know, more
decades on this planet than than him.
And go yeah, what is it actually? How
are you thinking about this? What do you
not understand? What have you not had
time to experience?
>> So empathy to me is is the key not just
to like being a good person. It's key to
the virtue of justice. But like when you
look at most of the the enormous
blunders of history, you know, Iraq,
Vietnam, fundamentally, it's this sense
of like, well, here's what we think
should happen. Here's how we think it's
going to go. And then this um this
inability to conceive of the other
people in the equation as being rational
or reasonable or even uh uh significant
actors, right?
engraved on the temple of Apollo where
the the the oracle of delicat said you
know uh one of the one of the epigs
famously uh we know one of the famous
ones is know thyself but the other one
is offer a guarantee and disaster
threatens right so you think you know
how it's going to be you think you know
how it should be this is often exactly
what precedes like the biggest blunders
of history the lack of empathy to go
what do they think what do they want
what are they going to do if we do this,
right? And so I think there's there's a
number of kind of blind spots or um uh
impediments to our intelligence or
wisdom. And and so really um
being wise is the removal of some of
those things like Socrates, you know,
someone is sent to that same oracle to
ask why Socrates is so wise because he
doesn't think that he's wise. And it
comes back, you know, he's the wisest
man in Athens and as Socrates thinks
about it, he realizes cuz he doesn't
think that he's the wisest person that
he is in fact wisdom. So it's like what
are the if if we go hey I want to be
wiser I want to be smarter it's stepping
back and going well where am I being
stupid like what are what are the things
that are making me stupid that that are
impeding my judgment impeding my ability
to discern to see what's really here and
how do I strip those away that's how we
get wiser do you know the idea from
mathematics of never multiply by zero
>> no
>> okay so um take as big of a number as
you want uh 2,343,000
times it by 5* by 52 times by 17 million
times by 0ero
>> you get zero right so you never multiply
by zero and it's basically an argument
that you can continue playing the game
as long as you're not kicked out to the
reason that using too much leverage when
you're trading is a bad idea that going
bankrupt is a bad idea you can spend all
of the time that you want looking after
your health you eat a grass-fed diet you
avoid seed oils and red 40 but one day
you decide to not wear your seat belt in
the car
>> yes sure
>> zero yes
>> uh you spend Your teenager is working
very hard at your education. You make it
to university. You're just about to
start on this brand new adventure. And
you have unprotected sex and get
somebody pregnant.
>> Not quite zero, but [ __ ] big big
change.
>> Avoid the the major stupid things.
>> Correct. Avoid the major stupid things.
And um that idea of okay
in the world of business and in the
world of sort of objective outward
metrics of success I probably should
double down on my strengths because my
highest point of contribution is where
all the gains acrue to the very very top
right power law. So move yourself up. Oh
you're 99.5 get to 99.6 that's really
great. It's a huge big change. However
when it comes to life like the
shortcomings are what's going to kill
you. There's a a great idea from
Visakhan Verasami and he says he calls
it uh the divorce paradox which is uh
why do people who are seemingly the best
friends in public uh so reliably end up
breaking the marriage apart? And it's
because we don't realize that the bad
times and the way you deal with bad
times are a much better predictor
>> of long-term marriage success than how
much you enjoy the good ones. Nobody I
would I would estimate most marriages
don't end because of too few peak
experiences.
>> Sure. Many will from too many and two
too much rupture without repair
effectively. Like that is what
>> pulls you down into negative equity
within a relationship and you can
reinvest that back in. But really the
it's like calories, right? Why is it
that you control your diet more than you
control your expenditure when it comes
to exercise? because it's way easier to
eat 400 calories than it is to expend
them. And I think marriage as the
non-married guy in the room is uh
similar to that. That the amount of work
you need to do in terms of good things
to offset that [ __ ] [ __ ] argument you
just had last night is an awful lot. So,
hey, control your calories. Like, make
sure you get good at at repair after
rupture in the same way as ensure that
you don't multiply by zero in your
personal life. I was just thinking of a
couple more things that smart people do
that make them stupid. One is like you
don't deal with your childhood issues,
right? So you you are very smart, you
are very successful, you are very
powerful, but there is a part of you
that's uh an 11year-old. There's a part
of you that's an angry teenager and that
person is is not who you trust with
these high stakes.
>> Have you done um much sort of emotional
work? Uh what's that look like? Yeah,
the the inner child work I think is
really key. When you find it when you
find that kind of very young, very
impulsive, very impetuous, very
sensitive part of yourself, that's
usually something that you haven't dealt
with. That's kind of a state of arrested
development inside you. Like that, you
know, there's the there's the uh they
say there's the adapted child, right?
The child that has to the thing the
decisions the assumptions you make about
the world because your environment was
not perfect growing up, right? Those are
coping mechanisms that made sense when
you were 13 and your parents were
splitting apart or you know you were
unattractive nerd who was bullied or you
know you you you lost a bunch of people
that you you you make these you were
abused. You went through these things.
So you made certain assumptions or
adaptations to to survive that. And
maybe that's not good now that you're
the leader of a company of a thousand
people or that you're you know making
films in Hollywood. you you can't afford
to be that 13-year-old, right? So, I I I
think you sometimes you see people, you
know, like this is the classic midlife
crisis, like you're blowing up your life
because there's some part of you that's
like trying to get back to some earlier
part of you, right? And so, I think you
can see people who have sort of very
smart, very rational in most aspects of
their life, but they're making sort of
very impetuous,
>> irresponsible decisions because they're
they've left something unressed. The
other the other thing I think we see
people do that makes them stupid is like
and this goes to the idea of information
uh diets, but I think I I've as I've
gotten older, I've just seen more and
more smart people that I know just kind
of lose it like lose like go crazy,
right? Like like your your inputs are
very important and also taking care of
this vessel
>> is important and so you know I think
sleep deprivation is cumulative. The
drugs you take are cumulative. The
stress you put on yourself is
cumulative. Your the lonely nights is
cumulative, right? The the hours that
you work is cumulative. And you know,
you
you get to a place where something
snaps, right? Uh John Stewart Mills, one
of the smartest people who ever lived.
He has this crazy education and he snaps
at like 20 years old. Um you know, you
can only wind the rubber band so tight.
>> And and I think you see that So people
people make really bad decisions and
it's it's this it's like this trauma
that they're not addressing and then
it's producing new trauma in the present
moment.
>> There's something that sort of fall is
especially in someone who's really
really smart. It feels
extra catastrophic pitiful. Um there's
this sense of, oh wow, it happened to
them.
>> Mhm.
>> Therefore,
how am I a mere mortal protected from
this thing?
>> Well, they're actually more vulnerable
to it than you are. Because imagine
you've gotten really used to trusting
your instincts. You've gotten really
used to being right.
>> You've gotten really used to making
contrarian bets. Like a friend of mine
said, you know, having a making a
contrarian bet that you turn out to be
like massively right about can be a
brain destroying experience.
>> Oh, that's so great because you've just
learned that everyone else is an idiot
and you're really smart. And that that
even though everyone is pointing out
this problem and that problem and what
about this and what about this, you are
you are learning the wrong lesson from
that which is like not like oh this is
the one in a thousand times. You're like
no no no this is every time. And so
often that's why people who build like
transformative companies or artists who
are had this reputation for being
transgressive and you know they get
themselves into trouble later because
>> they drink their own Kool-Aid. They're
just playing that same thing again and
it's different circumstances.
>> I think we all have this sense that our
view of the world is the right one,
right? We're all biased toward that and
if there is a time where your view of
the world seems to be uh contrary to
most or all other people and you get to
stand at top this big pedestal and say,
>> "Fuck you all. I was right."
>> Yes. Uh the allure to think run it back
like we're doing it again.
>> Yes.
>> Is so strong.
>> It's and and this goes to what we're
talking about though is like okay so
that's a historical fact, right? Like
there are so many great historical
examples of that same thing happening.
So you want to learn you want to see
that so you can recognize the pattern in
your own life which is almost certainly
not going to be as catastrophic or as
significant. Right? So when I went to my
publisher in 2011 and was or 2012 and I
was like hey I'd like to write a you
know about stoic philosophy they were
like what you know and and that was not
a thing they were excited about. Now, I
ended up being obviously very right
about that, but I try to actively think
about why they thought it was a bad idea
and in what ways they were right
>> and in what ways I was correct, but only
accidentally. So, you know what I mean?
Like, I wasn't this far-seeing genius
who predicted all of this was going to
happen. I had an idea for one thing that
I wanted to do.
>> So, question on that. how and I I I put
myself in the camp of someone who uh
doesn't have the courage of his
convictions as much as I think I should.
>> I think uh not fantastic at listening to
my instinct, not fantastic at listening
to my gut, very sort of top down, not
bottom up, very sort of existing above
the neck.
>> Um for me, I get the sense that it would
probably be a good thing for me to maybe
go, I think I'm right on this and I I'm
going to commit to that. Um what is your
what give me the the the contrarian
perspective on this?
>> What you want to do is go okay I'm
having this feel like I'm I'm doing this
and I'm getting this push back or people
are questioning it for this reason or it
seems you know like a impossible task
for this reason and then is the part of
me that's resisting that uh ego or is it
like no I have secret knowledge here. Is
it that I've really done the work? I've
really thought about this and I have an
answer for that. Right? I think about
this when I get edits back on my book. I
don't like getting edits, right? Is my
objection to the idea of am I feeling
this as the 15-year-old who doesn't like
to be told what to do or and some of
those notes that is what's happening and
I need to put I need to talk to that kid
and go this person is trying to help
you. You should listen to them. And then
there's the part of me that that knows
what I'm trying to do and knows what I'm
trying to say and has really thought
about this and I have an answer to why
that's not a correct bit of feedback.
and distinguishing between the impulsive
emotional resistance and the sort of
rational uh courage of your convictions
is a different is these are very
different things and I think that's
really important and so
>> it's probably better that you're not uh
you know
>> blowing [ __ ] up on a whim
>> miss yeah this sort of missionary uh you
know profit thing of like that's that's
what's going that might serve you well
until eventually it blows you up
>> higher likelihood of multiplying by zero
Yeah, by doing that.
>> And so, so I go I try to think about,
okay, I wanted to write these books
about stoicism, this book about
stoicism, and it turned out I was right.
What are the good lessons to learn from
that? And what are the lessons, the lies
that I want to make sure I'm not taking
from that?
>> And then, you know, like this bookstore
that I opened, you know, like it was a
stupid idea. It was crazy. It shouldn't
have worked. It did work. Now, why did
it work? It was because I I thought
about why it would work and I minimized
the downside and I I
>> turned it into a [ __ ] office.
>> That's not the lesson. The lesson is not
when I feel like doing something, I
should just do it. And people, you know,
are always trying to hold me back. And
and so those are just like a couple
minor examples in my life that that I
was able to learn and recognize in the
moment because I watched, you know,
because I've read about, you know, this
Nobel Prize winner who thinks they found
a magical cure for this. I mean, like
Newton got into like alchemy. You watch
how smart people learn uh the wrong
lesson from their success. And then you
want to make sure that when you
experience success or you have these
analogous moments in your life, you're
like, "Okay, this is my opportunity in a
low stakes, lowkey way to learn the same
lesson as opposed to needing to
escalate, escalate, escalate to
eventually learn it catastrophically."
>> I love that idea of sort of a a dose
response um or there's a particular
waterline that you need to get past in
order to have this unteachable lesson.
Well, some people are more and less
teachable than others. Yes. Um, so I
guess
we mentioned there what are some of the
impediments of intelligence to wisdom?
Another interesting question would be
something like what are the prices that
a wise person pays that an unwise person
doesn't? What are the costs of being
wise?
>> Yeah. I mean self-consciousness it can
be tricky. like there is a you've never
done it before, you know, you don't know
how hard it's going to be. You don't
know what to be wary of. You don't know
what to be intimidated by. You can just
plow ahead, right? And I do think in
art, creativity, business,
self-consciousness is sometimes an
impediment. It's an it you're
overthinking, right? And so wisdom, if
wisdom paralyzes you, if wisdom makes
you think about everything from every
angle, uh, and thus deprivives you of
the energy or the enthusiasm to do the
thing, that can be a real problem. I
think the other the other
side effect of wisdom, although it's not
really wisdom, but they can be
associated with each other, is like a
sort a certain cynicism, right? Like uh
Fineman talked about how like you
shouldn't lose the wonder like you know
he says you look in through a microscope
he says you know does it make your heart
flutter it should still make your heart
flutter and there is something where the
the the byproduct of the learning and
the understanding and the experience
the years of it can make you kind of
jaded and cynical and that
that's sad and tragic and I think you
you have to it shouldn't deprive you of
hope. It shouldn't deprive you of
purpose. It shouldn't deprive you of
these really wonderful things. It just
means you have to work for them in a new
way.
>> Mhm.
>> Ryan Holiday, ladies and gentlemen.
Dude, you're great. I appreciate you. I
can't wait for
>> the Stockdale book. Uh, where should
people go? Keep up to date with the
million things that you
>> uh Daily Stoic. Daily Stoic on YouTube.
I think my name on YouTube. I don't
know. Just Google around. They'll figure
it [ __ ] yeah, Ryan. I appreciate you.
>> Thanks, man.
>> Thank you very much for tuning in. If
you enjoyed that episode, well, first
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