JORDAN THIBODEAU:
Ryan Holiday is
a media strategist
and prominent writer
on strategy and business.
After dropping out
of college at 19
to apprentice under
Robert Greene, author
of "The 48 Hours of Power".
He served as
director of marketing
at American Apparel
for many years.
He has written,
"Trust Me, I'm Lying--
Confessions of a Media
Manipulator," "Growth Hacker
Marketing," "The Obstacle is the
Way," and "Ego is the Enemy."
So please join me in
welcoming Ryan Holiday.
All right, Ryan.
So for my first question--
it's a good interrogation--
so what is the ego
and how can it get in
the way of our success?
RYAN HOLIDAY: I'm not talking
about the Freudian ego, which
is probably sort of above
my pay grade to talk about.
I'm talking about sort
of the colloquial ego.
I guess I'm talking about
the Trumpian ego, right?
When you think you're
better than everyone else
and you think you
have all the answers.
When your sense of your
own skills or values
far outstrip the reality of
your situation, I would say.
There's a line from
Bill Walsh-- he's
saying ego is when
competence becomes arrogance.
So I think it's that line
where you're not just
competent in what you're doing.
You think that you are
God's gift to humanity.
And I'm not saying that everyone
is an egomaniac and only
egomaniacs need to sort of
think about the role of the ego.
I'm saying that we all
make decisions out of ego
at various points in our lives.
These are usually big mistakes.
These cause problems for us.
So what I think happens is if
because of your sense of self
identity you detach from
reality in some way,
it makes whatever it is
that you're doing harder
than it needs to be, right?
If you're an artist and
you sort of detach yourself
from reality, you're
not going to be
able to relate to your audience.
If you're a business
person and you're
not able to see the flaws
in what you're doing
and are not able to
listen to your customers,
your products are going to
get worse, so on and so forth.
So I think realism--
a sense of the world
that you live in--
is really critical to most
of the things that we do.
And I think ego gets
in the way of that.
JORDAN THIBODEAU: So how do
we become aware of our ego?
RYAN HOLIDAY: It's interesting.
I think most people are good at
diagnosing ego in other people.
We're really good at
judging other people
and saying, why is he doing
this or why is she doing that?
Like, they have no idea what
other people think of them.
But we don't really apply
that sort of sense of rigor
to ourselves.
So the book is about
thinking about why you're
doing what you're doing, right?
Victor Franco has this line--
between stimulus and response,
there's a choice, right?
Or there's a pause.
And if you can pause
there and you can reflect,
you can decide whether
you want to respond
or how you want to respond.
What I'm sort of talking about
is stepping back and evaluating
what our motivations are
in a given situation, why
we're doing things, why we are
attracted to certain things.
And just making sure that
we're doing those things
for the right reasons
rather than because we
want to impress other people.
Because we think it says
something about us as a person.
And sort of just getting rid
of some of those more selfish
motivations from
what we're doing.
JORDAN THIBODEAU:
In your book, you
have a quote that says,
"Ego loves the idea
that something is fair or not."
You mentioned the
persecution complex.
What is that and how can we
protect ourselves from it?
RYAN HOLIDAY: Well, so one
of the themes in my writing
is stoic philosophy, which
is an ancient philosophy.
It was popular with
the Greeks and Romans.
And one of the most
famous practitioners,
Marcus Aurelius, who's
the old guy in "Gladiator"
that Joaquin Phoenix's
character kills.
Philosophy is a loaded
word for a lot of people.
Tim Ferriss-- he calls
it an operating system--
I think that's a better
way of thinking about it.
It's really a set of
exercises and sort
of tweaks to your
perspective that
allows you to function better.
And one of the things
that the stoics talk about
is the story we tell ourselves
about the things that happen,
right?
So if I called you
an asshole right now,
you would have to think
about whether I was joking
or whether I was
being serious, right?
And if you thought I was joking,
it wouldn't hurt your feelings
and if you thought
I was being serious,
you would interpret
it as an attack.
And so that interpretation--
how we determine what
an event is or means--
that's something
we control, right?
And so they're saying
events are objective.
Marcus Aurelius says,
there is no good or bad--
there's only perception.
There's only what we
think about things.
So to answer your question,
I think what happens is--
and this is kind
of related to ego--
I think it's more of just a
general problem that we have--
we look at a situation
that we're in
or we look at a situation then
another person is in-- maybe
it's someone we're competing
with or we're jealous of--
and we go, is that fair?
Should they have that
while I only have this?
Is it fair that I got fired?
Is it fair that this went
wrong or that went wrong?
And the reality is there
is no fair or unfair.
There just is.
And spending a lot of
time labeling things,
in my experience, often
prevents us from--
one, prevents us
from solving things
but it adds an
extra burden on top
of just dealing with whatever
this thing is in front of you.
So I think once you
see the stoics do
a lot is sort of strip the
interpretation out of things
and look at what they are.
I think what ego often does is
it does the opposite of that.
It adds a bit of our own
identity to a given situation.
It looks at how this makes us
look in front of other people.
It's concerned more with
appearances than reality.
JORDAN THIBODEAU: Another
quote that stuck out to me
is you said, "We
tend to overwork
as a means of self
escape, as a way of trying
to justify our existence."
And this is a quote
from Josef Pieper.
How does that also
tie into our ego?
RYAN HOLIDAY: There's
some article--
I forgot where it was.
I read it this
morning on the plane.
And they were talking about--
the stereotype of millennials
is that we're lazy.
But actually, a significant
portion of millennials
are workaholics.
The term they're starting
to use now is work martyrs.
And basically, it
means like you think
you're so important to whatever
it is that you're doing
or whatever your job is that,
literally, the world would
end if you didn't do it.
And I've felt that
myself many times.
And this is, of
course, absurd, right?
Someone sent me
an email yesterday
and they had a
line in it I like.
They were saying, if you
were really indispensable,
then you can never be promoted.
So it's not great
to be indispensable.
You're not Atlas.
The world is not sitting
on your shoulders.
I think what happens is that--
maybe you didn't have
a ton of confidence
as a kid or you didn't feel like
your parents appreciated you--
you can start to mistake
accomplishments in work
or throwing yourself in
work as a sort of a way
to buttress your identity.
It can make you
feel good instead
of just intrinsically feeling
good as a human being, which
is what your right is to do.
I sense this in my
own life, right?
Relationships are complicated,
but work is easy, right?
I can be fighting
with my wife and I
can get up and leave the room
and sit down on my computer
and it's not fighting
with me, right?
There's no complications there.
It's just simple
and straightforward.
And so I think
oftentimes, instead
of dealing with difficult
things that we face in life
or dealing with
ambiguity or uncertainty,
we want to immerse ourselves
in work or tasks or activities.
And it's a way of feeling
good about ourselves.
But it's ultimately sort of
running from our problem.
JORDAN THIBODEAU:
Why do people feel
they have graduated in
certain fields of expertise,
causing them not
to learn anymore?
And how do we remain
always a student?
RYAN HOLIDAY: The book
is split into three parts
and the first
section of the book
has a section called,
Become a Student.
So it's sort of taking up the
beginner's mindset, right?
There's a quote from Epictetus,
the stoic philosopher.
He says, "One cannot learn that
which they think they already
know."
Right?
And I think this is true.
If you go--
especially when you're
young-- if you think
you know everything
because you went to this
college or that college
or you started this
company or that company,
you're not going to
learn anything, right?
You can't learn what you
believe you already know.
And you can't learn if you
think that you're the smartest
person in the room.
So I think that's one problem.
That's how ego manifests
itself early on in our careers.
But then what happens is we
start to become successful.
We accomplish something--
and you see this a lot
with CEOs and politicians--
you get to a point
where you are the
best at what you do.
And learning can stop
there too, right?
You're no longer challenged in
the way that you were before.
You might know more
than other people.
And so that atrophies.
And there is going
to be someone else--
maybe it's 5 years in
the future or 10 years
in the future-- someone else
isn't atrophying in the way
that you are.
And they're eventually
going to catch you.
And so I think you have to
maintain that student mindset,
right?
There's a quote
from Emerson I have
in the book who says, "Every
man I meet is in some way
my superior and in
that I learn of him."
Basically, he's
saying that you have
to go around and look for the
things that you're not good at.
And you have to improve.
Socrates was considered
wise because he
knew what he didn't know.
So it's that idea.
John Wheeler, the
physicist-- he's saying,
"As our island of
knowledge grows,
so too does the shore
of our ignorance."
And I think what you
realize is that if you
think you know everything,
you've stopped learning.
That's one.
But the second part is actually,
the more that you learn,
the more you are exposed to
things you haven't learned.
You have that hunger.
If you have that drive to
constantly be exploring that--
exploring the fringes of
what you're butting up into--
that's a recipe for not
just continual improvement,
but also, it suppresses
the ego, right?
It prevents you
from thinking you're
better than other people,
because instead of thinking
about all the
things that you know
versus what they
don't know, you're
thinking about all
the things that you
don't know compared
to some other person
that you're modeling
yourself against.
JORDAN THIBODEAU: Interesting.
One story that
stuck out to me was
your story about Jackie Robinson
and what he went through.
Could you elaborate on that?
RYAN HOLIDAY: Yeah.
Obviously, I've not
experienced anything remotely--
and most of us in this room
have not experienced anything
remotely like the discrimination
that someone like Jackie
Robinson would
have gone through--
but it's interesting when you
look at his life, especially
his early years.
No one would have
predicted that he
would have been the guy
that integrated Major League
Baseball.
Not because Jackie Robinson
didn't feel strongly
about equality and civil rights
and wasn't a talented athlete.
It was that he felt too strongly
about these things, right?
He got into fights all the time.
He got arrested.
In multiple instances,
police officers
pulled guns on Jackie Robinson
because he was resisting arrest
or he was fighting.
He would get into trouble.
And I think any of
us reasonably would
react that way to sort
of blatant discrimination
and racism.
And he was in the Army.
He got kicked out of
the Army, basically,
because he refused to go
to the back of a bus, which
he shouldn't have had to do,
but someone was insisting.
And then the way he handled
that was so over the top
that he ended up
getting a discharge.
So anyway, he is not who
you would have predicted,
because when Branch Rickey, who
was the manager of the Dodgers,
was looking for someone--
he wanted for a long time
to integrate Major League
Baseball.
He wanted to hire
a black player.
And he had a few
different players in mind.
And he has this famous
meeting with Jackie Robinson.
And he's asking him, what
would you do in this situation?
What would you do
in that situation?
A waiter does this.
You get refused
access to a hotel.
Someone throws a pitch at you.
What do you do?
And he was testing
Jackie Robinson.
He said, I'm looking for a
player who has the guts not
to fight back, because he
knew that racist players would
be attempting to goad him
into responding in such a way
that they could then use that
to kick him out of baseball.
So to me, what was so impressive
about Jackie Robinson is
that his entire time in Major
League Baseball, he never
he never got in a fight
with another player,
even though people said
horrible things to him.
They actually would
slide spike first--
which is something
you are not supposed
to do in baseball-- at him
to try to take out his legs.
They would taunt him.
He was hit with dozens and
dozens of pitches on purpose.
But he never fought back.
He sort of channeled all
that energy and that rage
into playing.
And that's what
made him so great.
And it's ultimately what
allowed other players
to follow in his footsteps--
that entire experiment could
have been set back if he
had responded differently.
And so to me, the analogy is
I think we all face examples
like that in our lives.
Again, not as severe, but
you're the youngest person
hired by a certain company.
Your wife or your husband--
their family doesn't approve.
You are going to be goaded.
People are going to
say things to you.
You're going to
be underestimated.
How are you going to
choose to respond to that?
If you are ruled
by your emotions,
if you're ruled by
your passion, if you're
ruled by this sense of
justice in the short term
and you insist on getting
your satisfaction in respect
to every one of
those situations,
you're not going to
make it very far.
You have to be able
to bite your tongue.
You have to be able
to think long term.
You have to have some sort of
sense of mission and purpose
that allows you to transcend
the petty concerns in a given
situation.
You get shit on a lot when
you try to do big things.
And you have to be comfortable
with that and OK with that,
and you have to be able
to persevere through it.
So that's the story.
JORDAN THIBODEAU: Yeah.
That was a great story.
And one of my mentors--
his name was Frank--
and he went on to become one
of the first African-American
directors of a
prominent tech company.
And he had a history--
he actually marched with
Dr. Martin Luther King
during the Civil
Rights movement.
And he got brought in through
the tech company's diversity
program.
And there was another
African-American before him
who was just as
qualified, educated.
But he went through brutal
racism through the company.
And because the way he responded
to it, he was pigeonholed.
And that person became a
mentor to Frank and basically
gave him the same advice
that Jackie received,
which allowed scores of
other African-Americans
to follow him and actually
earn other positions
in corporate America or
nonprofit work, which
weren't accessible
to minorities before.
So what are the
positive aspects of ego?
I mean, we talk about
arrogance, but could there
be a positive aspect
when people, let's say,
lack self-confidence
in a situation?
RYAN HOLIDAY: Well,
one of the things
I've spent a lot of
time thinking about
is that exact question, right?
You don't write
a book saying ego
is bad without maybe spending
a couple of seconds thinking
about, they have
some positive traits.
The way that I define it as
sort of delusion and arrogance
and superiority and this
sort of group of traits--
I would say, no, I
don't think there's
any reason that you
want to introduce
those things into your life.
Now, is confidence important?
Absolutely.
But I want to make the
distinction between confidence
and ego.
I talk about this
a lot in the book.
The distinction is that
confidence is earned.
Confidence is based on fact,
on experience, on information.
And ego is based on--
if confidence is
what is real, ego
is what we wish
to be true, right?
Aristotle has this concept
of the golden mean, right?
And so he's saying that
every virtue is basically
the midway point between
two vices, two extremes.
So he's saying courage is
halfway between recklessness
and cowardice.
It's right there in the middle.
Or generosity is
halfway between--
again, sort of giving your
money away and being tight
fisted, right?
And so I think I
would put confidence
in the middle between ego--
sort of self-absorbed
superiority--
and then on the
other, ironically, I
think a lot of people who
are crippled by self-doubt
just spend too much time
thinking about themselves.
They think they know everything.
They think they know why
you're screwing them over,
and why this will never work,
and all of these things.
So I consider confidence
and humility in some ways
to be synonyms, right?
Humility, it literally
means lowliness.
But the definition
we have of humility
is someone who sort of knows
their strengths and weaknesses.
They accurately see themselves.
They don't think they're
better than anyone else.
They're sort of
inwardly focused.
To me, confidence is similar.
Confidence is knowing what
you're capable of, right?
It's saying, hey, I know
I can do this because I've
done similar things before.
Or I know that I'm
a quick learner,
I know that I'm
not going to quit.
Those are things
to be confident in.
Just going in and thinking,
hey, this is going to be easy,
I'm the greatest there ever was.
Or not even bothering to
stop and think about what
would happen if it turned out
to be harder than you expected
or whatever.
That's where ego is
problematic, right?
JORDAN THIBODEAU: And I
think a lot of startups
in Silicon Valley-- and
you're going against the odds
as a startup company.
So you have to puff yourself up.
RYAN HOLIDAY: Well,
you think you do.
You think that you do.
But this is typically a bad
starting point in my opinion,
right?
So obviously, yes-- you
are going into something
where the odds are
overwhelmingly against you.
But lying to yourself
does not change those odds
in any fundamental way.
I think what's actually
courageous and brave is to say,
hey, I'm doing this thing.
I know that it's risky.
I know that it's hard.
But I'm confident
in my own abilities
that if it is
possible, I can do it.
Marcus Aurelius says this line.
He's saying, if it's humanly
possible and you're human,
then you can do it, right?
And so that to me
is not delusional.
But going in and
thinking, of course,
I'm starting the next Facebook.
And in two years, I'm
going to sell it--
having this sort sense of
certainty about something that
you cannot be certain about
that is predicated on numerous
contingencies that are
outside your control--
I don't see how
that's productive.
JORDAN THIBODEAU:
And in thinking
you're the next Facebook,
you're missing a lot of steps
in the process, right?
RYAN HOLIDAY: Yeah.
I mean, look, you sit
down to write a book.
If you tell yourself
you are writing
the great American novel,
that might help you
with your nerves a
little bit, but it
doesn't help you write the next
great American novel, you know?
Kanye West is not a great rapper
because he has a huge ego.
He's a great rapper because
he's a great rapper, right?
Because he put in the work.
He learned how to do this and
he spent hundreds and hundreds
of hours doing it.
So to me, it's all extraneous.
That's not why people
are good at what they do.
Sure, in the way
that, let's say,
a drug might mask an inner
pain for a short amount of time
before it escalates
into an addiction,
I think you can see a similar
thing with ego, right?
If you're starting a
company, writing a book,
moving across the country
to become an actor--
these are scary things.
And you can numb
yourself of that pain
through ego and
narcissism, I guess,
but that's all it's doing.
It's not making
the pain go away.
It's just numbing it slightly.
And often, I find that it
pops up in other places.
JORDAN THIBODEAU: Right.
What are three things we
can do to check our ego?
RYAN HOLIDAY: Well,
I think just thinking
about it is the thing that
most people don't do, right?
They're not asking,
why am I doing this?
Why is this so important to me?
Why do I feel like
I need to be right?
They're not asking
that question,
and I urge people to do that.
I think the thing we were
talking about earlier
about always focusing
on what you don't know,
focusing on what there's
left to learn-- to me,
what I love about writing
is that it's an inherently
humbling thing to do, right?
Every day, I wake up and it's
not as good as I want it to be,
and it never will be as
good as it is in my head.
So that suppresses
the ego attack.
Attaching yourself to some
larger pursuit of mastery,
I think, knocks down
the ego a little bit.
And the big thing for me
is sort of disconnecting
and experiencing something
greater than yourself.
I think that's
another part of it.
So it's hard to feel like you're
that important when you're
in the Redwood forest, right?
When you're surrounded
by things that
are older than you
will ever live to be,
that are taller than
you will ever be,
that could crush
you in an instant.
I think going out and
experiencing nature,
experiencing timeless things is
another way to sort of combat
the ego as well.
I think oftentimes, if you were
living and breathing your work
and that's all you're
thinking about, it does.
It becomes the most important
thing in the world to you.
And that skewing
of your priority
can hold you back as well.
JORDAN THIBODEAU: I think
something we commonly
deal with here at Google or
any other places where there's
competition and you're around a
lot of people who are bright--
I consider myself the
Forrest Gump here--
there's an exception made--
but have you ever dealt
with imposter syndrome?
RYAN HOLIDAY: Yeah.
Do you guys know what
imposter syndrome is?
I don't know.
I mean, I think
anyone who's going out
and sort of chasing that
brass ring-- when you get it,
you get it for a little bit.
You instantly feel that flip.
Do I deserve this?
What does this feel like?
Are they going to find me out?
I think you deal with that.
I think to a certain degree, the
less you think about yourself,
the less that comes up, right?
So the more you are
focused on the job
rather than how does everyone
think I'm doing about it--
what is everyone's opinion
of me is one concern.
And the other is, am I
doing the best possible job
that I can do?
I think the less you are focused
on what others are thinking
and what you are
thinking and you're
focused more in the present
moment of whatever you're
doing--
to me, that's a way to combat
that thing a little bit.
Especially with some of
the social media tools,
we kind of get the
sense that people
are paying attention to us
a lot more than they really
fucking are.
Like, nobody cares.
Nobody cares.
And nobody is watching,
you know what I mean?
JORDAN THIBODEAU: It would be a
good title for your next book.
RYAN HOLIDAY: The original title
I wanted to do for the book
when it was sort of about
a different topic was,
"Your Life is Not a Novel
and This is Not a Movie."
We think that we're in this
movie and that we're the star
and everyone's--
but everyone thinks that, right?
And so that doesn't work.
That's inherently in
conflict with each other.
So you can stop thinking that
there's this audience who's
like, observing your every
move and dissecting this--
like you're Kim
Kardashian or something--
the easier it is for you
to just focus on whatever
it is that you're doing.
So this imposter syndrome--
inherent within the logic
is somebody is trying,
is searching and trying to
find out who should be here
and who shouldn't be here.
And the reality is
no one is doing that.
JORDAN THIBODEAU: I think
Naval Ravikant for AngelList
says that everyone thinks
they are in their own movie.
RYAN HOLIDAY: Totally.
JORDAN THIBODEAU: And
he looks at situations
as if he has a challenge--
OK, maybe this person
is the part of the plot,
or this person can be
the villain or something.
Or maybe I'm the sidekick
in someone else's movie,
to take the centeredness out
of the whole entire story.
RYAN HOLIDAY: Well, I
think that attitude just
makes everything seem a lot more
important than it is, right?
You get this sense that if your
life has to correspond or feel
like a movie, you
have to exaggerate
the importance of everything.
The reality is if
your life was a movie,
it'd be a really boring one
and it'd be really long.
So maybe that's not
a great metaphor.
JORDAN THIBODEAU: Right.
That's true.
Yeah so another quote that stuck
out was from James Bashford.
He said, "It requires
a strong constitution
to withstand repeated
attacks of prosperity."
So how do companies
prevent themselves
from creating ego of
success and entitlement?
RYAN HOLIDAY: Yeah.
Well, I think we tend to be
on guard for the worst case
scenarios, and we don't
think that much about
how the good scenarios--
what changes they will bring
or how they will change us.
I think that's what he's
saying in that quote.
One of the famous lines
about Marcus Aurelius
is from Matthew Arnold, who was
a Christian scholar and writer.
And he was saying, he's
one of the few people who
was given absolute power
and he became better for it.
That's unheard of.
I mean, we even have that line--
absolute power
corrupts absolutely.
And I think you tend to see--
and I have experienced this
and I think a lot of people
have-- you experience
some semblance of success
and all of a sudden, you
have these new temptations
and these new responsibilities
and new stresses.
And they kind of make
you an asshole, right?
Because you have all
this stuff and you're
not prepared for
it and all of that.
And so I think a
company has to, I think,
internally make sure that they
are not supporting and enabling
those people who thrive
on dominating others
or think that it's
all about them.
But also, the company
has to make sure
that it's not buying
into its own hype, right?
That it realizes that they do
that analysis where it's like,
50% of the Fortune 500
companies from 1950
are not in the
Fortune 500 anymore.
Some even higher
number than that.
Your reign is very
short, even when
you're the best at what you do.
And so if companies can
embrace that and sort of
be open to the fact that
there's tons of change
and that industries
shift, then it
doesn't matter how
dominant you are
right now if you don't
think about those changes
and those shifts.
If you embrace that
disruption, it's
going to happen to
you anyway and you're
on the wrong end of it.
So I think it's also
important that companies
don't get that inner
ego that we're the best,
we're unbeatable.
And that's what happens
to sports teams.
It's why it's so hard to win two
Super Bowls in a row or two NBA
championships in a row.
Because the team
tears itself apart.
The egos ruin it.
JORDAN THIBODEAU: Gave me
a flashback of my Lakers.
Kobe and Shaq.
RYAN HOLIDAY: Sure.
JORDAN THIBODEAU: A
couple of championships
left on the table because
of politics inside.
In your chapter on Always Love,
you include the following quote
from Martin Luther
King, "Hate at any point
is a cancer that gnaws away
at the very vital center
of your life and
your existence-- it
is like an eroding
acid that eats away
the best and the objective
center of your life."
Can you talk more
about this quote?
RYAN HOLIDAY: Yeah,
I think anyone here
who's ever been screwed
over or hurt by someone--
I would ask yourself what the
emotions you felt afterwards--
were those a positive force in
your life or a negative force,
right?
So does the bitterness
or resentment or anger
that you felt for that person--
did it one, do anything
about the situation?
And two, did it alleviate the
pain that you felt at all?
And three, did it
improve your life, right?
And usually, the answer is no.
There's a quote
from Seneca saying,
you would never think to return
a bite to a dog or a kick
to a mule.
But that's what we do, right?
Someone hurts us, so then
we want to hurt them back.
Or someone says something
judgmental about us
so we want to judge them.
I think a better reaction
is obviously, compassion.
It's to try to think about where
this person is coming from.
There's a good line--
I think it's from
Socrates-- saying
no one does wrong on purpose.
Obviously, there's
sociopaths out there
in the world and
horrible people.
But generally, think
about all the times
that you hurt other people.
When you did it, were you
consciously attempting
to hurt them, or was it
that you didn't know,
or you weren't thinking,
or you were caught up
in the moment or
whatever, right?
And so it's like, we cut
ourselves breaks all the time,
right?
That's how we live
with ourselves.
But we cut other
people very few breaks.
And not only do we
not cut them breaks,
we hold on to whatever they
did to us and it eats at us
and we carry it around with us.
And so that chapter there
is that oftentimes, the way
ego manifests itself
when we're doing great
is one problematic form.
But the way it
manifests itself when
we're going through something
tough, when we lose,
when we end up on the
wrong end of something--
we often extend
that painful period
because we hate instead
of letting it go.
Or better, just
appreciating what
happened and the
people involved.
JORDAN THIBODEAU: Right.
RYAN HOLIDAY: Easier said
than done though, of course.
JORDAN THIBODEAU: That's true.
It's like drinking the poison
and expecting someone else
to die.
RYAN HOLIDAY: Yeah.
Yeah, that's exactly right.
That's a great line.
JORDAN THIBODEAU:
So you were talking
in your book about
outcome independence
and not focusing on results.
Can you share the
story about the writer
who wrote the
"Confederacy of Dunces"?
RYAN HOLIDAY: Yeah.
Has anyone here read "A
Confederacy of Dunces"?
It's an amazing book, right?
It's maybe the funniest book--
I would say the funniest
novel ever written.
It's just so funny that they
can't turn it into a movie.
Like, they've tried.
John Belushi, Will Ferrell--
it's been like this
perennial book.
They've never been able
to turn into a movie
because it's so funny.
Buy anyway, it's amazing.
This guy-- he wrote it-- his
name is John Kennedy Toole.
He wrote this novel.
He submits it to Simon and
Schuster, and they say,
no one is going to publish this.
This book is not good.
I'm sorry.
And here he argues with
them and they say, look,
it's not going to work.
He talks to a few other
people and basically, he
resigns himself to the fact
that it will never be published
and puts it in a
drawer in his desk.
A few months later,
he commits suicide
alone in a back
road in Mississippi.
He attaches a garden hose to
the exhaust pipe of his car.
And he dies.
And it's a tragic literary loss,
although people don't know this
at the time.
His mother finds the manuscript
a few years later in the desk
drawer he left it in.
She takes it, she reads
it, she thinks it's good.
She takes it to a
literary professor
in New Orleans
who happened to be
a writer named Walker Percy,
who's also an amazing writer.
He reads it, he
immediately recognizes it
as a work of genius.
He has it published by
the University Press
there in Louisiana.
And it wins the Pulitzer Prize
for literature that year.
So obviously, nothing
changed from the submission
at Simon and Schuster to
winning the Pulitzer Prize.
I mean, he was dead.
He didn't improve it
or anything, right?
And so this is the
problem with letting
other people's
opinion of your work
determine whether it's
valuable or not, right?
Obviously, ideally, they should
have seen it for what it was.
But people are
wrong all the time.
They don't know.
Some things are
ahead of their time.
Some things are decades
ahead of their time.
Some things are
just presented wrong
or it's the wrong moment
or whatever it is, right?
So I find it to be really
sad that literature--
instead of appreciating the fact
that he made this great thing,
he attached to whether
it was published
or not and how it was
received by an audience.
About not only whether
the work was worth it,
but whether he deserved
to be alive or not, right?
Which is obviously an
extreme interpretation.
And as a writer,
I relate to that.
Because you spend all this
time, you work on this book,
and at a certain point
it leaves your hands
and there's nothing else
you can do about it.
And this is true
for a lot of work.
But if, as a
creative person, you
have decided that the arbiter
of whether it was good
or not or whether your
time was well spent or not
is how it is received
by these other people,
you've now taken your
sense of self worth
and you deferred it out.
You've placed it in
other people's control.
And those people are going to
let you down from time to time.
They're not going to
appreciate what you did.
They're going to judge it.
They're going to be afraid
of it or whatever it is.
And so that's something
you have to practice.
Warren Buffett has a line--
it's better to live your
life by an inner scorecard
than an outer scoreboard.
What is it that you measure
your own success by?
And ideally, it should be
things that are entirely
in your control, right?
Like I know I
wrote a great book.
I know that was the
best work that I'm
capable of doing
when I wrote it.
I know how much
time I put into it.
Obviously, I want it to sell.
But it's better
that I go into it
aware of the fact that
it could potentially not
and that people might hate it.
And I have to be OK with that.
And if you're not, then it's not
the right profession for you.
And so that's something
we have to work at.
JORDAN THIBODEAU: It sounds like
if you focus on the results,
you can set yourself
up becoming a victim.
Saying people never
see things my way.
RYAN HOLIDAY: And
the other tricky part
is that the goalposts move.
So if you tell yourself,
if I'm a millionaire,
I'll feel good and valuable.
And then you get
a million dollars
and doesn't feel like anything.
If you think hitting the New
York Times bestseller list--
that'll make me feel good--
or marrying this
beautiful man or woman,
or sleeping with this number of
people, or having this house,
or making it in New York City.
Robert Louis
Stevenson is saying,
it's a difficult thing
to scale arduous hilltops
and find humanity indifferent
to your achievements.
That's fucking life, right?
That's just how it goes.
Nobody cares.
JORDAN THIBODEAU: That's true.
RYAN HOLIDAY: You have to care.
JORDAN THIBODEAU:
That's really important.
I remember I told
myself growing up,
if I can get off of Section
8 housing, I'll be happy.
Then I got off
Section 8 housing--
OK, if I can start investing
in real estate, I'll be happy.
I started investing in real
estate and this circle--
RYAN HOLIDAY: They call
that conditional happiness.
The idea that you will be
happy when this thing happens.
It never ever ever is true.
JORDAN THIBODEAU: Right.
So you talked a
lot about stoicism.
For someone just
getting into stoicism,
where do you find a
natural starting point?
Marcus Aurelius seems to
be the most accessible.
But some people are
wondering if you
think there's a better
place to start learning
about stoic philosophy.
RYAN HOLIDAY: I wrote a piece
for Tim Ferriss' website
a few years ago
called Stoicism 101,
Philosophy for Entrepreneurs.
That's a pretty
good entry point.
Marcus Aurelius is
how I got into it.
I think Seneca has
an essay called
"On the Shortness of
Life" that is a really
sort of beautiful moving essay.
It's short to read.
It's a problem that we all
deal with, which is that we die
and we don't know how much
time we have on this planet.
I'd maybe start there.
I'm working on a book.
I have a book coming out later
in this year called the Daily
Stoic, which is like one page
of stoic thought every day
like from the original Greek
and Latin translations.
But I would just say pick
up one of the originals.
They are very, very readable.
They're not what you think
when you think of philosophy.
But I would say
don't read whatever
is free on the internet.
They're free on the
internet because they
are archaic old translations
that use words and phrases.
Translation is an art.
And spend the $9 to
get a translation
from Penguin or something that
is at least somewhat modern.
JORDAN THIBODEAU: Right.
In your book, you have
a quote that's from you.
It says--
RYAN HOLIDAY: It's not
a quote if it's from me.
JORDAN THIBODEAU: Oh sorry,
a statement from you.
"This is the book I wish existed
at critical turning points
my own life.
When I, like everyone
else, was called
to answer the most critical
questions a person can
ask themselves in life--
who I want to be."
So who do you want to be?
RYAN HOLIDAY: It's a
very personal question.
JORDAN THIBODEAU: Just
imagine no one's here.
Just me and you.
RYAN HOLIDAY: Yeah.
Well, what I was
saying is that I
wanted the book to be sort of
a set of things to think about.
What the smartest
people in history
have said at various
junctures in your life.
And I don't think you
just are this one thing.
Obviously, I wanted
to be a writer.
But I also want
to be a good one.
I also want to be
just a good person.
I want to be a good husband.
I want to be a good father.
I want to be any of
these things, right?
So I don't think there's
one thing that I want to be.
And I don't think
I necessarily have
an answer to that question.
But it's a question I
think you're facing,
and what you want in those
moments is not to wing it.
There's this quote
I have from Bismarck
in the book that says, "Any
fool can learn by experience.
I prefer to learn by the
experience of others,"
is what he's saying.
And that's what I try
to do in my writing is
take the experiences of
others and organize them
in a coherent way that allows
people and myself to draw from
JORDAN THIBODEAU: Gotcha.
You have mentors, relationships.
When you have a conflict,
how do you deal with it?
And what gets under your skin
and kind of throws you off
your balance?
RYAN HOLIDAY: When I have
a conflict with a mentor?
JORDAN THIBODEAU: Or
just any mentors or--
RYAN HOLIDAY: I mean,
typically I find--
I'll give you this
one trick I found.
When I worked at
a large company,
I found that there would
often be conflicts between two
people-- you're
arguing over an email--
and someone wants to get
the last word, right?
I would decide when I would
have the last word, right?
So I'd be like, I said
what I'm going to say.
There's nothing that
you can say here
that's going to
change my opinion.
Basically, I remember I was
in this argument with someone
and I said what I had to say.
I've said my piece
and then I was
going to do whatever
I was going to do.
And they responded but
my phone ate their email
and I didn't see it.
And then like two months later--
so I forgot all
about it, I moved on.
And then I found their
response a few months later
and I read it and it
made me really angry.
And so I was like, if I just
never found this email--
and we interacted with
each other inbetween
and things had gotten better.
JORDAN THIBODEAU: Sort
of drumming up the old.
RYAN HOLIDAY: Yeah.
And so I was like, I
can just do this myself.
When I'm done I'm done.
Lincoln did this.
Abraham Lincoln-- he would get
in a fight with a subordinate
or a general or someone and he'd
write them a really long letter
describing all the things
that they did wrong,
that he was mad about, and
laying out his opinion.
And then he would
put it in an envelope
and he'd leave it in his desk.
And we only know that
a lot of these letters
existed because we found them.
But he would never mail them.
And I would say the vast
majority of conflicts--
it's not that you're
avoiding them.
But it's that if
you cease to prolong
and escalate them, they
eventually resolve themselves
and go away.
JORDAN THIBODEAU: True.
So going into our
society, what do you think
are the general character
traits and trends
of our current culture?
And what you think are the most
potentially dangerous things
about these treats that
should be addressed?
RYAN HOLIDAY: That's
a good question.
I would say a lot of the trends
that we're seeing are just
the timeless things.
People are selfish.
People are rude.
People are greedy.
People are scared.
There's nothing that's happening
in this current election cycle
that you couldn't find in
any history book, right?
Other than some of the
technical tools at which it's
being distributed by.
It's like, the
more things change,
the more they stay the same.
So I think that you can focus
on these new little things that
might be changing,
or you can just sort
of look at the timeless.
People have been
what they do forever.
So I just try not to spend that
much time thinking about it,
right?
I'd rather look at myself and
I'd rather look at the things
that I need to improve
in my own life and lament
that millennials aren't driving
enough cars, or buying houses,
or whatever the things
that people get upset at.
JORDAN THIBODEAU: Right.
Things you have no power over.
RYAN HOLIDAY: Totally.
And that might be a trend
or it might not be a trend.
In Texas, where I
live, the first three
years I lived there,
they were talking
about how there was a
drought all the time.
And everywhere you go, people
talk about this drought.
It's like that in
California now.
And then in one month,
the entire drought
was erased with 30
days of straight rain.
And so I felt kind of stupid
about how much time I thought
about this drought, right?
Because it's not a long
enough sample size, right?
How do you know if
it's a drought or not?
So I think we tend to get
concerned and wrapped up
with these things that seem
big and seem like there's
enough evidence for them.
But really, we're just
being very myopic.
JORDAN THIBODEAU: So
now at this point,
I want to give the
audience students.
Does anyone-- great.
RYAN HOLIDAY: So he's asking
philosophy to most people
seems academic and theoretical.
Stoicism as a school is unique
and how eminently practical
it is.
AUDIENCE: And it isn't easy.
RYAN HOLIDAY: Yeah.
It is and it isn't.
I would encourage you to read.
There's a book by a French
philosopher named Pierre Hadot.
It's called "Philosophy
as a Way of Life".
He's basically
saying that stoicism
in particular, but also
epicureanism and cynicism--
these were not
systemic explanations
of the universe the way
that we think they are.
Like Marcus Aurelius
was writing meditations
for his own private use.
He had no idea that you
and I would read it.
He probably thought it would
be destroyed upon his death,
right?
And you see this in
other philosophers.
Think about it this way--
"Nicomachean Ethics," which
is Aristotle's famous work,
was his lecture notes
produced by his son.
He's getting up there,
talking to a class
about a lot of things.
He's telling them what he
thinks they need to hear
on that day or this day.
It's not completely circular
definitive logical proof
for anything.
It's just what this smart
guy was thinking about.
But I think if you start
to interpret philosophy
as a way of solving
the problems of life--
Thoreau says this-- it's
to solve them practically,
not theoretically.
And Epicurus says,
"Vain is the word
of a philosopher which does
not heal the suffering of man."
That's what philosophy,
I think, historically
was supposed to be.
I think there's a decent
amount of evidence for this.
What happened as monotheism
and modern religion--
it was sort of created
somewhat around the same time--
Seneca and Christ are
alive at the same period--
we get this
distinction between--
religion is how you're
supposed to live your life
and what kind of person
you're supposed to be,
and then philosophy is
what you study in school.
But that distinction did
not exist previously.
AUDIENCE: So my
question actually
isn't about the writing.
But more along the lines of--
I was really curious
because you had
sort of a nontraditional path.
And I was wondering how
you went from the thought
to taking on something
new to taking action.
For example, leaving college,
taking a nontraditional path,
writing your first book.
How did you go from
speaking about it to action?
RYAN HOLIDAY: I think the
thing that most people make up
is that these changes--
they're epiphanies, right?
Like, oh, I woke up and I knew
that this is what I had to do.
I tend to find that these
life changing decisions are--
Have you read Thomas
Kuhn's "Structure
of Scientific Revolutions"?
Basically, it's saying we think
that scientific breakthroughs
are like Archimedes in the bath.
Like, I've got it.
In reality, it's a slow
accumulation that eventually
destroys an existing paradigm.
So you start to notice all
these anomalies and flaws.
And over time and
then eventually you
realize that the existing
explanation for a phenomenon
no longer applies and you have
to come up with a new one.
I think it's like that.
You think that this thing
was what you wanted,
and you're working at
it, and you're going.
But it's sort of accumulating.
And you can shove those feelings
down or you can sort of put
them over to the side and--
what is this?
I'm going to explore.
And it's a process.
It only looks clear
in retrospect.
Like, it looks like I
dropped out of college,
and I worked for this person,
and then I got this job,
and then I left that to do this.
And obviously, when I'm writing
my bio on the back of my book,
I only have four sentences.
I'm not-- and who
would have known?
So that certainty--
you want to make sure
you're not falling
for that certainty
and that you allow
things to develop.
And then at a certain
point, you do take risks.
You've got to think
through those risks
and make sure you're
comfortable with them.
But I think I would say
it's not from epiphanies.
It's not from any
sense of clarity.
It's actually the opposite.
It's, whatever is going on
right now is not working,
so I'm going to try
something different or new.
And that does end up
working for however long.
AUDIENCE: So what do you think
was the most important thing
you learned from Robert Greene?
RYAN HOLIDAY: I would
say practically,
it was learning how to
organize and make a book.
Like he just taught me
the craft of writing.
And then I would say as a
person, I think he taught me--
I think I'm intense and
kind of high energy.
Robert's very sort of
calm and dispassionate
and he judges things
slowly and I don't
feel like he's ever in a hurry.
And so trying and
failing-- but I learned
a lot from that example.
AUDIENCE: What was your
favorite passage from your book?
RYAN HOLIDAY: From my own book?
That is a question
I've not thought about.
There's a line in the intro.
There's lines that you
think are your best writing
and then sometimes you put
in things that are just you
thinking you're being
clever or whatever.
But there's a line in
the interim where I say,
when you finish this
book, I hope that you
will think less of yourself.
And I say I mean it in
both senses of the word.
Like you'll just be thinking
of yourself less, but also,
you won't think you're as great
as you currently think you are.
So I think that's clever.
AUDIENCE: Hi.
I read your book and I
have a question about one
of the characters
in your chapters.
Her name is Katharine Graham.
RYAN HOLIDAY: Katharine Graham--
she inherited the
Washington Post company.
She was one of the
great female CEOs.
Maybe greatest CEO
of the 20th century.
AUDIENCE: Right.
So I was putting
myself in her shoes.
She was facing a lot
of troubles and doubts
from herself, probably, because
she doesn't have experience
before.
So when do you draw the line
of pushing through, persevere,
versus, maybe this
is not for me?
I should just wash my hands
and go away and do something.
I was maybe like, Michael
Jordan trying to play piano.
It's not going to work out.
RYAN HOLIDAY: Yeah.
That's a great question.
And I don't think
there's some rule-- it's
like, here's the math equation
to know whether you should
do this or not.
There's a line from
Steven Pressfield I like.
And he's saying--
what is he saying--
remember that the counterfeiter
is wildly self-confident
and the innovator
is scared to death.
So in some ways, I think being
scared or uncertain about--
I think if she had known, hey,
even though I've basically
never worked a day
in my life, I just
inherited this
multinational corporation,
and I have no
experience, but I'm going
to be the world's greatest CEO.
I'm going to turn this
into hundreds and hundreds
of millions of dollars
of personal wealth
and people are going to
be writing books about me
50 years from now.
If she had thought that,
she would have been insane
and she probably wouldn't
have been successful.
So I think her doubts actually
fueled her being good,
because if she thought she
knew what she was doing,
she wouldn't have sought
out Warren Buffett
and learned from him.
And she wouldn't have
hired the right--
So I think that those doubts--
provided they're
not like, hey, I
don't know how to swim, I
shouldn't jump in a pool--
but provided that those
doubts are fueling
you to learn and explore
and stuff like that,
I think there can be positive.
AUDIENCE: How do you know
when a decision is ego driven?
It feels to me like
most of my decisions
are partially ego driven.
And I'm slightly
addicted or dependent
on external validation.
RYAN HOLIDAY: Sure.
AUDIENCE: So how do you know--
is it like a 51-49 scale?
RYAN HOLIDAY: Yeah, I
don't I don't know either.
Look, I'm not saying egolessness
is possible or even desirable.
But I'm saying that you should
be questioning and thinking
about these things rather
than having it sort of be
this silent thumb
on the scale skewing
your decisions or
your priorities.
Just because your
ego is lined up
with something that doesn't mean
that it's the wrong decision,
right?
You wanted to start some
company to prove people wrong--
that's not a great motivation.
That doesn't say anything
about whether the ideas are
good or bad, right?
So I think what
you're trying to do
is ultimately strip
ego out of the equation
as much as possible.
It's a process you get
better at it as you go.
But generally, the
fewer emotional, knee
jerk, insecure decisions
you make, the better.
I don't think it adds
much to the decision.
So if you can make
the right decision
for sort of pure
objective reasons,
obviously, that's better
than the egotistical reasons.
AUDIENCE: What's
the most crazy thing
that you've done
to market this book
and what's the craziest, most
controversial thing you've
seen in the last year
in terms of marketing?
RYAN HOLIDAY: Craziest thing?
I mean, I got the title
tattooed on my arm.
What?
AUDIENCE: Can we see?
RYAN HOLIDAY: It's on this arm.
I don't like that books
aren't fact checked.
Even traditionally published
books aren't fact checked.
So I'm driven crazy by the fact.
There's this popular book
called "Eat That Frog"
by this guy named Brian Tracy,
which is based on a Mark Twain
quote about how you should
eat a frog every morning.
Basically, do the most
difficult thing first.
Except Mark Twain
didn't fucking say that.
So it pisses me off that
someone could write a book
and-- you know.
So I wanted to write an article
about fact checking books.
So I just paid someone
to fact check my own book
so that I could write
an article about it.
I didn't do anything
crazy for this book,
partly because there's a
certain ego in marketing.
And I wanted what I did for the
book to be true to the book.
So I didn't do
anything crazy like I
have for some of my other books,
but I might in the future.
AUDIENCE: I dig your writing.
I was curious with--
Robert Greene was your
mentor and he wrote books
like "The 48 Laws of Power."
And so that seems to
be a certain mindset.
And I wonder if you absorb that
way of looking at the world,
then maybe that will tend you
towards thinking of things
in an ego centered way.
So I'm curious how
you'd respond to that.
RYAN HOLIDAY: Sure.
I mean I do think it's important
that you don't psychoanalyze
an author and their book, right?
So Robert Greene says
that his books are amoral.
He's not saying.
This is how you should be.
He's saying these are
the rules of power--
choose the ones you want
or don't want, right?
So having known him and
having worked with him,
I've seen that he is
not a ruthless, cunning,
exploitative, evil
person, right?
So I think understanding
how power works historically
and seeing the levers by
which people come to power
is neither good or bad.
It's just fact.
And then you decide, based
on your own moral compass,
how and whether you want to
follow in their footsteps
at all.
So, you know,
Robert Green writes,
"Let others do all the work,
and take all the credit," right?
Well I was his
research assistant
and people know about it.
So obviously, he was actually
very generous with the credit
that he gave me and has
been a great supporter.
And so I think
knowing how things
tend to work sociologically
or historically--
it doesn't mean you
have to live by them.
AUDIENCE: Thanks, Ryan.
RYAN HOLIDAY: Thank you.
AUDIENCE: Obviously, you
are clearly well-read.
What is your strategy for
being a better reader?
RYAN HOLIDAY: OK, so I'll
say a couple of things.
I'll just vomit out some
thoughts on reading.
Speed reading is not a thing.
Stop chasing it, right?
It's supposed to
take a long time.
There's no way around it, right?
You don't think about how to
speed up sex or eating, right?
These are things
you savor and enjoy.
I would say that I made a
decision early on in my life--
it's like, hey, I read
this thing in a book
and then I applied it at work.
So why am I pretending
that reading
is what I do at home
in my private time,
and then work is when I sit at
a computer and read it all day?
So the idea that reading
is part of my job,
I'm going to make time--
if I decide at 2:00 PM to spend
two and a half hours reading,
I don't consider that
me messing around.
That's work.
And it's not simply just
taking in information.
You have to do something.
You have to have some process
for synthesizing and organizing
and storing this information.
Otherwise, you're just
relying on memorizing it.
And I'm not a great memorizer.
So I organize it
all by note cards.
Some people use Evernote.
I think you also
have to organize
this information in some way.
And then I just
genuinely love reading.
It's my favorite thing.
And I would say the other thing
is I don't schedule reading.
I know some people are
like, I read 50 pages a day.
That might work for you.
I'm more of like a binge reader.
So I might read
four books in a week
and then not read
a book in a week,
depending on how I have time.
And I use travel.
I don't watch movies
on an airplane.
I read books, you know?
AUDIENCE: Thank you.
JORDAN THIBODEAU: Great.
Well Ryan, thank
you for everything.
RYAN HOLIDAY: Thank
you for having me.
JORDAN THIBODEAU: Let's give
him a round of applause.
[APPLAUSE]
