The STOIC SECRETS That Will Change Your Life FOR GOOD (Nobody Shares This!) | Ryan Holiday
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Ryan Holiday reflects on his career trajectory, noting how the very traits and strategies that propelled him to success eventually became obstacles if not managed carefully. He describes himself as someone who initially said "yes" to every opportunity, believing he could outwork anyone until it was humanly impossible; however, upon reaching a certain level of achievement, this relentless expansion turned into his worst enemy. Drawing on Stoic philosophy and insights from sports psychology, specifically an analogy about baseball players learning bat discipline after leaving the island of poverty, Holiday argues that once you arrive at success, one must learn to say "no" to protect their time and focus. He emphasizes that while early aggression is necessary for survival, sustained greatness requires specialization and the ability to prioritize what truly matters rather than trying to do everything simultaneously. The arrival of his son has profoundly shifted his approach to life, teaching him three critical lessons: protecting one's limited time from encroachment, understanding that "being" present is as valuable as action, and appreciating simple joys over constant intensity. Holiday explains how he previously stole time from himself and even his wife without much consequence, but fatherhood made the stakes higher because a child suffers if their parent defers costs into the future. He contrasts this with the Stoic view of physical property versus personal space, noting that we guard our bodies more than our schedules until forced to do otherwise by family responsibilities. This shift has helped him realize that happiness and great insights often come from stillness rather than constant motion, challenging his previous belief that action was the ultimate goal. Holiday delves into the mechanics of decision-making and feedback loops, illustrating how he uses a mental "filter" derived from Stoic principles to navigate criticism without letting ego interfere. He recounts an incident where he turned down significant money because accepting it would have meant working on something unfulfilling just for financial gain, realizing that buying freedom with money often leads to selling one's time and autonomy instead. To maintain objectivity, he employs Adam Smith's "indifferent spectator" test, imagining how a neutral observer would judge his actions to ensure they align with truth rather than ego or impulse. He also discusses the importance of seeking unsolicited feedback on books despite being an author, viewing negative reviews not as personal attacks but as data points that help refine work and avoid repeating mistakes, effectively using self-flagellation as a tool for improvement rather than dwelling in shame. Ultimately, Holiday defines success through three lenses: creative freedom to produce what compels him, the lifestyle flexibility to live without unnecessary constraints like unwanted travel, and continuous improvement where each new project surpasses the last regardless of sales figures. He warns against the entrepreneurial trap of believing "if I build it they will come," describing creation as only half a marathon followed by an equally demanding marketing sprint that many creatives neglect due to ego or misunderstanding their role. His philosophy centers on getting out of one's own way, recognizing that while certainty feels good and can drive progress, true mastery involves humility, the willingness to learn from failure, and the disciplined practice of reflecting daily—much like reviewing game film—to ensure actions align with long-term goals rather than immediate emotional reactions or financial temptations.
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Once you've arrived, the thing that got
you there is now in some ways your worst
enemy. And so that's something that I
have always struggled with is like I've
always been the person that just said
yes to everything. Early on in my
career, you know, it was like I can do
all of it at the same time. I don't care
if you think it's humanly impossible, I
will outwork you. I will I will make it
possible.
Yeah. So, where I want to start with
you, you talk a lot about people only
write the book that you couldn't not
write. Um it's got to be something that
really compels you and I love that and I
totally agree.
Sure.
What drives you?
I think what what drives me is is trying
to figure out the things that I wish
that I was taught
uh that I wish were part of what you're
supposed to learn in elementary school
and middle school and high school, you
know, um
philosophy was supposed to be
historically this. It they would call it
the guide to the good life, right? So,
it's something we've been thinking about
for a long time. But like where is this
guide? You know, like like I No one gave
it. I read a lot of books in school.
There were a lot of, you know, things
that they made us look at and nowhere
did I ever get this guide. And so I
think I I'm always sort of searching for
for the answer to that question, you
know, like how does one live? How is one
supposed to live? What do you do in the
morning? What do you do at night? You
know, how do you find happiness? You
know, the answers to these questions and
and so I'm looking for that personally
and then I think professionally my job
is to then share the answers to those
questions as I've as I find them.
That's really interesting. So,
especially now that you're on the
bandwagon of fatherhood,
Yes.
uh which I'm very curious to hear more
of your take on that. But like would you
ever write like for somebody in grade
school? Like that manual?
I usually am writing to a younger
version of myself when I'm writing.
That's one of the I think you have to as
a writer you have to have some idea who
your audience is. Like you have to be
able to envision that person and speak
to them. And so one of the people that
I'm always trying to speak to is me,
whether it's 5 years ago or 10 years ago
or 15 years ago. I don't know if I have
enough insight into where I was at that
age that I feel like I could really
speak to to that exactly. But, I do love
really well-done uh children's books. I
mean, like if you've ever read The
Little Prince, there's tons of lessons
in there. I think right now I'm I've
still got enough to say to me just a
couple years ago before I can go back in
time quite that far.
Right. What How had like the smile that
you had in your face, I want to make
sure we show that when I asked you about
becoming a father. How is it change the
way that you think or approach life?
So, my son is 13 months, so I don't have
a ton of experience yet. Uh
but I would say I'll give you three
three lessons. I say So, number one is
it becomes much easier to say no to
things because you realize we seem to
have a a limitless capacity to steal
time from ourselves, right? You know?
Yeah.
And the Stoics talk about this all the
time, you know, like we would go You
would be
uh incensed if one of your neighbors
encroached onto your physical property.
But, if one of your neighbors came over
and just talked your ear off for an
hour, you would find it rude to be like,
"Get out of here. I don't want to speak
with you." Right? Do you know what I
mean? Like So, we we protect our
physical space much more than we protect
our time, even though physical space can
be regained and time can never be
regained. And so, one of the things that
it's like e- even I've been married uh
for a while and and I've been with my
wife for a long time, I even found that
I I was comfortable stealing time from
her and from our relationship in a way
that I'm not comfortable stealing time
from a a child who I've promised as much
of my time as I can to.
Right.
Right? So, it becomes easier to say no
to in- inessential things. That's number
one. Number two, I would say is that
especially when my son was first born
was sort of learning that like parenting
is just actually just being there,
right? Like just physically in the
space. So, almost nothing else in my
life was would be like would sitting in
a chair not doing anything be doing
something, right? Right? And so, it's
it's really slowed me down in a very
good way, right? That like my job is to
sit here while he plays around on the
floor doing whatever he wants. I don't
need to be as purpose-oriented and
that's been a really good lesson for me
cuz I
That's really interesting. Why is that a
good lesson?
Because if you think that action is the
end-all be-all, you end up doing action
for the sake of doing action, right? So,
I I feel like I should always be doing
and doing and doing, but sometimes
you're just supposed to be. And
oftentimes just sort of being there and
sitting there and being still is where
really great insights come from. And
this is also where happiness comes from.
You know, it's hard to be happy and
appreciate and feel gratitude when
you're just moving all the time. It uh
my therapist said to me one time, she's
like, "You got to remember it's it's
human being not human doing, right?" And
and and the a kid is a really great
reminder of the the the the being part
because they're so always in the present
moment, right? And then I think the last
lesson is just sort of watching someone
experience sort of
just complete joy and again presentness
um is also a reminder that like things
don't need to be as I'm a very intense
person and although that intensity is
responsible for a lot of my success,
it's also responsible for my unpleasant
moments, right? It's responsible for
anguish that I feel or insecurity that I
feel and that the the need to be busy
all the time. And so, I think just
watching, you know, the simple pleasures
that he can enjoy I think lets me feel a
bit more gratitude and and appreciation
and then lets me focus on what's really
essential.
All right. Well, now let's ask a really
interesting question. At least I'm
deeply fascinated by this. So, now let's
imagine you wake up tomorrow and you
don't have kids. What of those things
would actually carry forward as
transformative elements for you?
I would say in a way they're all I would
carry forward all of them, but having
this having this person, this living
thing that you're responsible for, um
keeps those lessons top of mind because
there's real consequences for it, right?
reminder that you can't do everything
all at once, and you do have to
prioritize. There's someone who will be
upset, who will be hurt, who will suffer
for this,
rather than you just deferring those
costs into the future, which is what I
did before I had a son, and and what I
think most people allow themselves to do
all the time. You know, we know
objectively that we're going to die. We
don't have unlimited amounts of time,
but we still spend it as if we have
unlimited amounts of time because the
consequences are so deferred into the
future that we can get away with it. I
also intellectually knew all those three
things that I told you before, but it's
been good. It's been the hardest thing
that I've ever done, and and I think
it's good to challenge yourself that
way.
All right. So, abstracted from kids for
a second,
Okay.
you're you're you're a very methodical
thinker. So, what is the matrix by which
you make a decision for how to spend
your time or even what to strive
towards?
Look, I struggled with the time thing
before I had a kid. So, I'm all My
instinct is I I heard a great line from
Austin Kleon, and I I think he got it
from somewhere else. He was saying, you
know, the the job of or the mindset of
an entrepreneur or a creative person is
that you basically say yes to everything
until you can get to a position where
you can say no. But, it's really hard to
know that you've gotten to that
position, right? Especially because you
work yourself up into a state. I'll give
you another actually analogy. A friend
of mine, his name is Dr. Jonathan Fader.
He's a sports psychologist. He works
with the the New York Giants and the New
York Mets, and he was saying that in
baseball,
particularly players from like the
Dominican Republic, they have this
saying, they said, "You don't walk off
the island." So, basically, the only way
you can get out of poverty or out of
this place is by swinging, right? You
can only hit your way off the island,
right? And so, on the one hand, what
that does is it creates really
aggressive players. They swing at every
pitch they can. But, then as soon as you
make it in the major leagues, it's all
about bat discipline, right? You can't
swing at every pitch because the pitches
are better, because if you miss, it
causes problems for your team. And so,
it's this balance, right? Once you've
arrived, the thing that got you there is
now, in some ways, your worst enemy. And
so, that's something that I have always
struggled with is like, I've always been
the person that just said yes to
everything. Early on in my career, you
know, it was like, I can do all of it at
the same time. I don't care if you think
it's humanly impossible, I will outwork
you, I will I will make it possible. And
so, there was a time where
I don't think I ever ended one of the
opportunities that I had. So, I was just
adding them on top and on top, and I
never hit a wall. Like, I just never hit
it. And so, always saying yes, always
saying yes, that became who I was. And
now, as I've as I've achieved a certain
level of success, and what I've done is
gotten harder and harder, now it's all
about protecting the space that I need
to do that work. I think just the idea
of needing to make those hard choices,
knowing what's important, what's not
important, what I'm trying to
accomplish.
Not only have I struggled with that
already in my life, but then having a
kid makes the stakes of that higher, but
then it's also just a learning
experience. Hello, my friend. You know
that I believe success requires you to
see failure as the ultimate learning
tool. Success requires you to be
disciplined and gritty, and to never,
ever quit on your dreams. I say all of
that because one thing is certain, the
road to achieving your goal is not
smooth or linear. I wish it was, but
it's not. It's going to be bumpy,
sometimes scary. Some days you'll take
two steps forward and slide 10 steps
back. And that's why success also
requires you to know how to pull
yourself out of a rut and get unstuck
fast. Life is short. You can't be
messing around with your goals. You've
got to make progress every single day.
So, I've pulled a class from Impact
Theory University called how to get
unstuck, which you can watch for free
with the link on your screen or by
clicking below. When you join me for
that free preview of that workshop from
Impact Theory University, I'm going to
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goal, and keep your momentum. All right,
click that link and let's get to work.
All right, I'll see you on the inside.
There's a concept in Perennial Seller
which truly haunts me and is is clearly
the sign of the thing that I struggle
with along these lines, which was
nothing has destroyed more great artists
than the thought that they can do two
mutually exclusive things at the same
time.
Yes.
I butchered the quote, but
Sure. No, no. Right.
you get the idea. And you've said that
of your consulting business, you feel
like all you do is untangle people's
like mess of things that are often
conflicting that they want to do. What
what is it about that problem and how do
you help people through it?
Well, I think what I what I'm saying is
that often times people go, "Okay,
here's really what I want to do, and
this is what I'm trying to accomplish."
And then they see all these other things
that other people are doing, and then
they they kind of see that as like a
grab bag, and they're like, "I don't
want a little of this, and a little of
this, and a little of this, and I want
it all at the same time." That's not
really possible, you know? You can't
play five sports at the same time. You
got to pick one, and you got to
specialize. Maybe you can do two, but
you probably can't do five, right? You
can't be a classical musician and a rock
star, you know, and this and this all at
the same time. So, it's about sort of
picking your lane and then knowing that
some
some goals are mutually exclusive. The
question I ask clients the most is like,
"What does success look like for you on
this project?" And I get them to really
describe it to me and let's say there's
more than one thing in there. I go,
"Now, if you could only pick one of
those things and the other ones didn't
happen, which one would you pick?" And
I'm trying to get them to sift through
some of that conflict so we can really
hone in on what we're trying to do. And
often times, like where ego comes in is
like we've got the things that impress
other people and then the real
meaningful impact that we're trying to
have. And often times, I'm not saying
that the the status things aren't nice
and they're not they they're not
impressive and they're not cool, but
we've got to make sure that they're not
coming at the expense of those other
things.
Right. I love that notion of, you know,
asking yourself what success looks like
for you and having that clarity. And how
important is that clarity, do you think,
for people that want to be successful?
Like, how much of this is you start with
a goal that is abundantly clear and then
you create a path?
I think one of the things that has
really helped me make some of the
decisions we were talking about earlier
is what is like an ideal day of your
life look like? Like, maybe not right
now, but like what do you want a day in
your life to look like? And so, if if
that day is like, "Look, I'm the kind of
person I love going to an office. I love
lots of responsibility. I love lots of
pressure. I thrive in that environment."
Well, then great. You know that that's
where you want to end up. For me, when I
think about like the high-powered
executive whose whose whose entire
company is resting and falling on,
I think, "How does that person have time
to do any creative long-term thinking?"
I don't think that they do. And so, I
had to realize that oh, these two paths
cuz I was on two paths. I was a a writer
and a researcher and then also I had I
was at a big company that they were
mutually exclusive, that one was coming
at the cost of the other. And I tried to
do both for a long time. I At one point
I stupidly
doubled down on the one that I didn't
want and I realized it occurred to me
one day. I was I was actually in LA.
There there was some chaos at American
Apparel and so I gotten called back in.
paying me great money and it was like,
you know, 9:00 a.m. I just gone for a
run. I'm sitting down and I was writing.
I looked at my watch and I was like, oh,
I have to be at the office. Like if if
I'm not at the office, like people are
going to be mad. They're going to wonder
what they're paying. And and then it was
like, but my dream is not going into an
office. The most important thing for me
is to have the freedom to go where my
day takes me, especially creatively. I'm
on a path that's taking me further away
from what I want my ideal day to look
like. That's not success, you know? And
so, and Tim Ferriss has talked about
this. It's, you know, some people it's
like, my
um
dream life is being on a beach in Bali.
Well, what does that actually cost?
Could you have that now? Do you have to
have a life that you don't like so that
at the end of it potentially you're
lucky enough to go there? Or could you
find a way to get that now? I'm trying
to think about this on a regular basis.
Is my life resembling what those days
are supposed to look like? And if I have
too many days in a row that don't
resemble what I want my day to look
like, I go, I'm I'm I'm having the
opposite of success. You know what I
mean?
And what do you do very tactically in
that moment? Is it journaling? What does
that look like?
So, I I do journal every morning and
every night. So, part of my journaling
is just like a detailing of events.
Like, not for history, but just so I'm
forced to recount what happened and
actually think about it. You know, the
Stoics would say prepare for the day
ahead and then you're supposed to
reflect on the day that just passed. And
so, that sort of process of preparing in
the morning and reviewing in the evening
allows me to never get too far from
where I I want to be. You know what I
mean? Like I'm never going to I'm never
going to wake up 5 years from now,
hopefully, 5 years from now and go,
"This is just really not the life that I
wanted." Because I'm I'm doing the a
regular series of check-ins.
So, going back to what you said about,
you know, for a brief moment I actually
doubled down in the thing that I didn't
want.
Yeah.
Which I totally get and understand in a
way that I can't even convey to you.
Why do you think people have a hard time
identifying what they really want? And
like what can people do to not find
themselves in that situation?
This is a very first world problem, but
I would say one of the hardest things to
do
in the world is to turn down money.
Right? So, like I was in a conference
room and someone said, you know, "Look,
we need you to come back. Look, we know
you have this writing thing."
This is when you're quitting.
Yeah, or I had already basically left. I
was I was like sort of remote and and
and didn't have a day-to-day role. And
they said, "Look, we we need you to come
back. You know, this is going to be a
tough, you know, series of months, but
we think you can make a contribution. We
need you to come back." And I said,
"Well, look, you know, I've got all this
stuff." And they they said, "Well, what
would it cost to get you to come back?"
And I threw out what I thought was a
high number and they said, "Done."
And so, in that moment I was like,
"Well, that's a lot of money. If it
would it would be irresponsible to say
no to this, right?" And so, I was
telling myself one that I could do it
all at the same time. And then two, that
like, you know, I I wanted this money.
Like, you know, and and it would it
would seem dumb to say no to it. I do
with lots of successful like
entrepreneurs and and athletes. And one
of the things they're always talking
about, they're like, "Oh, I just I love
books. I love writing. I would love to
be able to do that." And so, one of the
things that struck me in that period
where I was unhappy was it was like, "I
get to do this thing that other people
tell me they wish they could do. And
here I am taking a bunch of money to do
the thing that they say they don't like
doing, you know? This is This doesn't
make any sense at all. And so I had to
back myself out of that situation. I you
know, I left some money on the table as
a result. And it was it
wasn't a fun experience, but it was it
was just I think in that moment I wasn't
thinking, "What do I want my life to
look like? What's the most important
thing to me?" I was thinking, "How many
zeros are in this check, right?" And
that
is not a great uh way to make decisions
in your life. Because what do people do
with their money? They buy freedom,
right? But oftentimes they give up
freedom to get money. And so that it was
like, "Oh, I could just skip those steps
and stay where I am and be very happy."
That was so interesting, man. So, yes, I
think that that's a an eternal thing
that people do with their their work
They're giving up their freedom in order
to buy some sort of future freedom,
which may or may not ever come, by the
way.
Right.
Um
Cuz what if what if you do that then you
get hit by a bus?
Yeah, or the money never comes.
Sure. Sure.
Which is maybe even more likely, right?
It just always slipping into the future,
the eternal future. So, my question is
though, and there's there's two things
really. So, one, how did you deal with
whatever the reverse of buyer's remorse
is, right? Where you give the money
back, and then that next time that you
want to do something and realize I can't
cuz I don't have the money, but oh if I
just stuck it out. And then yeah, we'll
we'll start there.
It's not like
uh I was choosing between, you know, the
poorhouse and, you know, paying for my
groceries or something, right? Like this
was this was extra. One of the
pivotal conversations in my life was
with Tim Ferriss when I was starting my
company. And he said, "You know, Ryan,
what do you do with your money?" And um
I was like, "What do you mean?" He's
like, "What do you What do you spend
your money on?"
And I was like, "Nothing. Like I just I
I like
I just put it in a bank account and then
I try to manage it responsibly. I live
pretty reasonably and and
I I I try to save my money and whatever.
So he's like, "Okay, so why are you
going out and trying to get more and
more if you don't need it?" And and that
was really helpful to me. So now
uh
when I'm thinking about clients,
uh like
what my test is at Brasscheck is we go
like, "Okay, is this work we're going to
be proud of or is this giving us money
that we need to do something we will be
proud of?" That test is really really
important. A lot of times people are
saying yes to money not because, "Hey,
if I do this then I can pour it into the
movie project that everything depends
on." It's like, "I need this so I can
lease a nicer car."
Right. One one concept I'm assuming it
comes from Stoic philosophy and I can't
remember if I read it in Perennial
Seller or
or both perhaps, but what would a person
more humble than me learn from this
moment?
Yes. That's something I think is
incredibly powerful. Walk people through
what that means, what you're trying to
get to, and what the result is of
approaching things like that. Well, I
think there's this cool exercise
uh from Adam Smith, who was the
economist. He he he wrote The Wealth of
Nations, but he also wrote a book called
The Theory of Moral Sentiments, which is
this sort of brilliant book about
philosophy and kind of like why we do
the the right thing basically. And one
of the things he he was talking about is
you is like you should judge all your
actions. He should you should subject
it, he said, to the indifferent
spectator test, which is like what if
there was a a totally impartial person
who you didn't know who's just standing
there watching you.
What would they think of this? You know,
what how would they judge what's
happening? And that's a way to sort of
step out from your own logic, your own
impulses, your own natural feelings, and
sort of judge, you know, if you're not
religious, you're not like, "What would
Jesus do? You're like, what would some
random guy think of this? And if if it
doesn't pass his test, it's probably not
a good thing to do, right? And so, I
think that's that's the test I go is
like, what would a person who isn't so
caught up in this, who whose identity
isn't on the line, how would they react
to this rude remark? Or how would they
react to this lowball offer? They would
not be nearly so caught up in it. It
wouldn't threaten them the way that I'm
feeling that right now. So, I'm going to
borrow a little bit of their
objectivity, and I'm going to try to I'm
going to incorporate it into my reaction
here. Now, in the way that therapy is
about questioning our thoughts,
philosophy is giving us the tools to in
the heat of the moment, you know, Victor
Frankl would talk about how, you know,
there's this between stimulus and
response, there's like a a moment, and
that's where we get to choose who we're
going to be. And I think philosophy is
about that moment, really.
How often do you think about that moment
for you very specifically? Like, do you
have a codified set of So, I think of my
mind is a a Pachinko ball machine, if
you know what those look like, where you
drop the ball on the top, it bounces
around over a lot of things. And those
things that it's bouncing on is my um
the code that I live by, right? My
belief system. So, I take something
negative uh or, you know, there's
nothing good or bad, but thinking makes
it so. So, it's like and I put it
through all of that so that I get a a
resulting outcome that is useful, which
is how I think of it. Do you spend a lot
of time building something like that?
Yeah. Yeah. You know, we're not robots,
so we can't like, okay, I'm not going to
react. This is like an intuitive, almost
an unconscious process, right? And and
so, you're sort of you're trying to
you're trying to put all this
information in there. Uh you're trying
to to to sort of put in those those
little points that the thing is bouncing
around on on the way down as a way of
sort of slowing down the process. I
think most people, your average person
who who doesn't work on themselves,
who's not reading, who doesn't care
about any of this, they're just they're
they're the time between stimulus and
response is like nothing.
Right.
And the the more you work on it, the
more you practice, the more you're able
to question your own thoughts.
So, what is that? Slowing it down?
that practice process look like? Like,
how do you practice that?
That's a good question. I mean, it it'd
be like how do they practice uh swinging
a bat in baseball? I mean, they just
swing it a lot and they they watch film
of themselves, so they're stepping back
and evaluating things after they happen.
They're looking for cues. They're
they're they've got other people around
them who are giving them feedback. I
think it's about a sort of cultivating
an awareness and a process of continual
reflection on the data that your life is
creating all the time.
Do you think most people do that,
though?
No, of course not. That's why it's such
a huge competitive edge to start working
on that. Do you know what I mean?
Yeah.
And and the earlier you start working on
it, the sooner you're going to start to
see results, but the more those results
are going to compound over time. There's
nothing in let's say Stoic philosophy
where we're saying that, you know, the
the idea that there's no good or bad,
there's just the interpretation that we
have on things. So, I first learned that
when I was 19 years old. I'm sitting in
my apartment in college and I read this
book and some person 2,000 years ago
said that to me. So, I had that was the
first time I encountered it
intellectually. A week later, uh that
would have only a minuscule impact on my
life, but every every time I've thought
about it, every time I've studied it,
every time I've tried to reflect on how
in retrospect I could have done that
better, I've accumulated
slightly more know- more knowledge, more
appreciation, more set more sense of
that, the truth of that, and and the
I've gotten better and better at it. I I
might be only 20% better at it now, but
I'm hoping that at 70 that that return
will compound not unlike my retirement
savings, right? Like you're
thinking about this and working on it
and writing about it and talking to
other people about it and and trying to
evaluate your own behavior and then it's
just this process of of reflection and
miniscule improvement as you go. And
you're not trying to get to perfection
right now. You're just trying to get a
little bit better than you were
yesterday or an hour ago.
Do you read Ray Dalio's principles?
I have not read it, but I've heard
amazing things about it. I I know his I
know I know a bunch of the principles,
but his practice is similar, right? He's
like, "We're recording all our meetings.
We're getting feedback from people in
the office about how you're doing." One
of my favorite stories about that Pete
Carroll, the coach of the Seattle
Seahawks, one of the best coaches in the
NFL, he was talking about how, you know,
coaches are constantly filming their
players and they're forcing the players
to break
to break down game film. They're
ruthless. Like it's like you could have
a great game and then the next day
you're you're back in the practice
facility and, you know, the receivers
coach is telling you
what a horrible game you had and all the
opportunities that you blown. And and so
obviously that's that's what makes these
guys so great. And coach Carroll was
saying like, "I realize I don't do that
to the coaches." Like the coaches never
experience that. And so he started
filming his coaches and he would he
would force them at the beginning of the
season to look back at all the times
that they blew it, right? That they lost
their temper or that they missed
something. And and so I try to do that
in my own life. I mean, one of the ways
that I, you know, authors aren't
supposed to read their own reviews for
instance. One of the reasons that I read
most of the Amazon reviews, let's say,
on my books is that I want to get
feedback from people. So I'm not reading
them to feel like I'm awesome or to to
sort of whip myself, but I I want to see
what people are responding to and I want
to get unsolicited feedback on the
writing. I have a a filter that I put
that information through, but I'm
looking for as much feedback as I can
about the things that I do so that I can
incorporate that data and and get
better.
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Uh, so this this is like my life's
obsession, this moment right here. So,
one, I want to know what that filter is
and we'll get to that in a second, but
so
you're you're incredibly successful,
right? You've got your own company, it's
doing well, working with the biggest
companies ever, you're a multiple-time
best-selling author, and you have
perennial sellers in the mix as well,
which is sell sell sell sell sell. Why
the hell do you subject yourself to the
self-flagellation of an Amazon review.
Like what what is that about?
Well, I it's not self-flagellation. So
you have to make that distinction.
How do you prime yourself mentally for
it not to become self-flagellation?
I can't change what happened. So I'm
looking for this feedback for tips and
information that can help me improve so
that that person who let's say they
didn't like what I did, so that I can
not let that happen again. They'd say,
you know, Ryan, uh I really like this
book but I can't let my son read it
because he uses the F-word a lot. And so
it's like, okay, so some people don't
like cursing. And then I noticed as I
went through the the positive reviews,
no one ever said, I really like how Ryan
curses a lot. So this was a this wasn't
something that was important to me,
right? And here it was having a negative
impact on some of the readers. And then
let's say a marginal to no impact, no
positive impact to the readers who were
enjoying it. So to me that's a pretty
easy data point to go like, okay, in
some cases I think I need to drop an
F-bomb here to catch people's attention,
right? And I can see that when I talk if
the audience is
you know, sort of drifting a little bit,
I can call I can use it, you know. Um
but there's no reason for me to do this
in my And so in in The Daily Stoic there
the there's no curse words. And that was
an improvement I think that I made the
book better and I got that by going
through this process.
That makes a lot of sense. Now Now talk
to me, you said you have like an
installed filter that you use to know
what to listen to and what not to listen
to.
Yeah, look at the feedback you're
getting and then remember what you were
trying to do. For instance, I'll I'll
get a criticism from let's call them
Stoic fundamentalists, right? People are
really sort of nerds about philosophy,
um who will say, you know, Ryan,
um
you know, Ryan doesn't add anything new.
He's just taking Stoic principles and
illustrating them with stories. Right?
So, that'll be one criticism. Or they'll
So, they'll say, "You should read the
originals. Don't read Ryan's book." Or
other people will say,
um you know, "Ryan is taking these
timeless virtuous principles and then
illustrating them with famous successful
people and, you know, that sort of
cheapens it or, you know, that's that's
uh
that's not what Stoicism is about, let's
say. Well, in both cases, I was
explicitly trying to do the thing they
were criticizing me for, right? So, I
say in the book, "If you're really
interested in Stoicism, go read the
ancient Stoic texts. I cannot do better
than them." What I was writing The
Obstacle Is the Way and Ego Is the Enemy
is for people who don't have time or
interest in ancient philosophy, but are
trying to improve their life in some
way. So, I'm trying to meet them where
they are. So, when someone says that I
didn't do this thing that I explicitly
wasn't trying to do, my filter is going,
"Okay. This person shouldn't have read
the book. This wasn't for them. I don't
need to take this personally, right?" If
you're trying to be everything for
everyone and you read feedback, you're
just going to get more lost cuz some one
person's going to say this and another
person's going to say that. But, if you
know, "Here's exactly what I was trying
to accomplish and here's what that
success looks like," then you can you
can filter this information and go,
"Okay, is this person's advice getting
me closer to where I want to get or
further from where I want to get?" And
that has been really helpful to me.
What I love about that and I really hope
people are listening to what you're
saying is you're doing it with an eye
towards getting better. To me, there's
an element and this is why I brought up
um
Principles by Ray Dalio is his thing is
all about like, "I'm just trying to get
to truth."
Yes.
And one of the things that I wish on
every human being is to one day in some
way, shape, or form understand what it's
like to be an entrepreneur in that if
the company does well,
fortune can be yours and if it does
poorly, you can lose everything.
Sure.
The amount of [ __ ] that cuts through
is crazy. Like, it's not even
necessarily that I don't want to have an
ego. I would love to have a big thriving
ego, and people are always saying like,
"How do you stay humble with the
success?" Dude, because if I don't, I'm
going to lose everything.
No, the the reality of how low the
margin for error is is like the ultimate
recipe or sort of shortcut to humility.
Like, let's say we're I'm fighting with
um
uh an editor or someone or even just a
friend who's reading one of my books
about, you know, the use of this
sentence or this paragraph or this
stylistic or you know, something in a
book. I don't have the room to be like,
"You don't know what the [ __ ] you're
talking about. Like, I'm the genius. Let
me do this, right?" Because if I'm
wrong, I don't feel so secure in uh what
I do that I feel like I can afford to
let ego make any of those decisions. I
have to let truth make those decisions.
So, you know, there's a a writing adage,
it's like when when someone says that
something's wrong, they're almost always
right. I think this is true in life.
When someone says there's something
wrong with what you're doing or, you
know, how you're carrying yourself or
what you're you know, a project or a a
product, um they're almost always right.
When they explain why it's wrong or how
to fix it, they're almost always wrong.
So, it's like when someone's saying
like, "I don't like chapter six."
They're right. They don't like chapter
six, right? When they say, "You should
get rid of chapter six or you should,
you know,
make chapter six the opposite of what it
is or get rid of this or they're
probably wrong, but you should try to
figure out why chapter six isn't working
and improve it and make sure that it's
aligned with your vision cuz maybe it's
not. Or, if it's perfectly aligned with
your vision, then you have to make the
tough call and go, "Look,
I'm not going to please this person."
All right. So, now the million-dollar
question is how the hell do you know the
difference?
First off, you you just go like
like, I'll give you an example. I I I
I've talked about this before, too, but
like one of the dangers of
entrepreneurship is or making anything
is that like people around you are going
to be like, "That's not a good idea.
Don't do it." And then you don't listen
and you do it and you end up being
right. Well, you've kind of just learned
a a very dangerous lesson, which is like
just disregard what other people say.
So, one of the reasons you tend to see
people on the way up, take a company
like Uber, they're just like blowing
past conventional wisdom
business best practices. They're doing
it their way over and over and over
again and they're going up and up and up
and that's creating a feedback loop
where it's like
the rules don't matter. We do it our
way. We do it our way. And they're being
rewarded for it over and over again. And
then at some point they cross a line and
now all of a sudden they started to do
things that are illegal, that are
unethical, that their customers aren't
going to like. But there's a delay
between doing that and being held
responsible for that and that's where
the sort of catastrophic explosion and
consequences inevitably come in. And so,
whenever you feel yourself going, "I'm
just going to blow past what everyone's
saying. They're all idiots, you know,
they don't know." That's a really bad
sign that you're probably doing
something out of ego. So, I think that
certainty is something I'm always
nervous about. Like uh so, it's become
sort of a cliché in entrepreneur circles
and you've probably read this article,
you know, the idea of like it's it's
hell yes or hell no, right? Like you're
either you're either a thousand percent
on it or you say no. But all the
difficult decisions I've ever made in my
life were like, you know, 51-49.
So, so it's like in some ways I'm
actually really skeptical. I I think
that there's a great point in that
article, which is like just don't do,
you know, don't do stuff just cuz you're
supposed to. But it should be tough and
if it feels easy then I want to question
that. I guess is is one of my answers.
And then look, nobody said writing a
book or being a leader or, you know,
shepherding some vision. No one said it
was going to be easy and clear and you
were going to know. These are things
that are going to keep you up at night
and that you got to roll the dice on to
a certain degree. And so, you just do it
and then, if you're wrong, you learn and
you do it better next time.
How do you keep your emotions out of the
way? Like I I have a very simple
formula, which is the thing that I want
in this world I want so desperately that
and it's not an ego thing. So, it's very
I have an ego for sure, but it's very
easy for me to set that aside.
It's not the thing that I want most.
Okay.
And so, in those times of like
emotionally I want to do this, but then
I just check it against oh, does it
actually help me get where I want to go?
No, okay, cool. Then I'm going to go
after that thing. What mechanism do you
have for dealing with that?
Well, what I I think one of the best
ways is just time, right? Abraham
Lincoln famously, whenever he was like
really mad at a subordinate, like, you
know, one of the generals in the Civil
War, he would write them like just a
really nasty letter. Like he would just
this is what you're doing wrong. This
is, you know, he he would write
everything that he wanted to say. And
then he'd put that letter in an envelope
and then put it in his drawer and then
wait, you know, a day or a week. And
then most of the time he wouldn't send
it. And so, one of the things I try to
do is I go like
do I really need to respond to this
right now? Because that tends to be
where that emotion The emotions are
typically immediate, right? Like I'd
find even the things that I'm really
upset about, I'm most upset about them
when I first find out about them. If I
give it a weekend or if I sleep on it,
I'm much less upset about them and I'm
going to be more rational and I'm going
to be more
responsible with how I reply. So, I I
just want to give it some time. I mean,
one of the tests that I have
I do this with emails a lot. Like if I'm
fighting or if I'm arguing with someone,
I'll go like, what if I just pretend I
didn't get their response? Like I'm not
even going to read it. Like I know like
I just said I just said my piece
and then they sent me a response back
like 5 minutes later.
I'm just not going to I'm just going to
delete it, right?
And then I'll let them have to resend it
to me or just let the issue drop, right?
So, I'm kind of just sticking my head in
the sand, but I'm I'm really just
creating a space for there to be less
cuz they're not going to resend the
exact same thing. They're going to Hey,
we need to talk about that thing. I'll
go, oh, what was it? And then we'll, you
know, we'll
we'll have a little bit of more
reasonable of a dialogue. When I feel
that impulse is like, I got to deal with
this right now, that's emotion and
that's probably not going to get the
best solution out of things.
What are things that wind you up, to use
a nice British phrase?
That get me pissed off?
Yeah. You know, when people mess with my
stuff. So, like if I like writing is
about what I'm trying to accomplish,
right? And so I did it the way I wanted
it to be done and I'll get really upset
like if something comes back to me even
if it's small and like a change is made
without like I'm very open to taking
criticism and feedback, but like I I
caught something, let's say, with a copy
editor recently on on a book I was
working on where like they reworked
something without they just assumed I
would be okay with it and they reworked
it and I caught it and that was very
upsetting to me, right? Because if I
hadn't caught it, something that I
didn't sign off on could have gone out
to the my readers, but you know,
I was much more upset about it at 3:00
on a Tuesday than I was the following
Thursday when I finally got to the
bottom of what happened and I worked
through it. It's just never that great
to act out. Oh, actually, I'll give you
something cuz I think about this
question a lot, too. And so, I've asked
some of the basketball coaches that I've
that I've worked with or have read my
book. I was like uh I was like, do you
ever get like a technical on purpose?
Because like a coach, you know, the
worst thing a coach could do is get so
mad about something that they give the
team the opposing team an extra point,
right? So, obviously, you don't want to
get a technical on accident like cuz
you're just ripped abroad by your
emotions. But sometimes
you should get upset to send a message
to your team, to send a message to the
refs, you know, to get the crowd going,
whatever it is. And so I'm I I was like
that I'm I'm interested if I'm going to
use my emotions, I want to be calm
internally, but projecting the emotional
response that's going to be effective in
that situation, but I don't want to be
jerked around by those emotions
unconsciously. Did that That's
advanced class [ __ ] So this is
something I don't often talk to people
about, but is is absolutely necessary, I
think, to certainly be running a company
is A, you've got to be able to control
your emotions so that you're not getting
whipped around, as you said, but B, you
have to understand that all of this,
even emotions, expressed, suppressed,
facial expressions, all of it is a
performance meant to convey something.
And once you understand that you can
leverage outrage, intensity, anger,
whatever the case may be, as a tool
Yes.
to move somebody down the road, then you
can really start to become effective.
Well, think about it this way. If you
yell at your people every time something
is wrong, they'll just be like, "Oh,
Tom's a yeller." And if I just
don't mind being yelled at, I can get
away with anything. Do you know what I
mean? That's a very That happens in
companies a lot. It's like you have to
be calcul- in some ways calculating and
controlled
and choose what you're going to get
upset about, otherwise the people that
you're projecting that to aren't going
to be able to discern a minor mistake
from a catastrophic mistake. It's very
important that you're not the the boy
who cried wolf, you know, the the one
who's who's uh
screaming about inconsequential matters,
and then when someone messes something
up, when they cross that red line,
they're not going to take it seriously,
cuz you're like, "Look, you yelled at me
yesterday cuz the the coffee was cold."
And, you know, here you messed up
something on the calendar, or whatever
it is. that you've got to you've got to
be able to use the Those are Those are
emotions, how you articulate what you're
feeling, or your, you know,
how you're going to act in a meeting, or
how you're going to,
you know, present a plan. That's a
communication tool, and you've got to be
able to use that. You can't just be,
"Oh, I'm not feeling it, so I'm down
today, or I'm in a shitty mood, so I'm
going to be yelling today." That's not a
good way to make those tough decisions.
I think of Ego Is the Enemy and
Perennial Seller somewhat as compendiums
to each other. I don't know how you
feel.
Um
What And I guess if you don't, I'll give
you my reasons for that. If you want to
create something great,
Yeah.
you need to get your ego out of the way,
right? So, that's sort of the moral of
the story for me, right? So, the
Perennial Seller addresses how to
actually tactically create something
that's great, but you can still feel the
Ego Is the Enemy elements in it, where
it's like
Yes.
you're ultimately the one that's going
to stop you, or propel you forward.
Yes.
So, taking that concept of if you want
to create something great, this is how
you get out of your own way, what are
like the three or four things that
people need to do, think, believe,
whatever, in order to achieve greatness?
Well, I So, number one, like, what are
you actually trying to do? Cuz you can't
do 15 things at the same time. So, like,
here's what I'm making. That's the the
main Like, do you actually know, right?
Cuz sometimes people are trying to do
too much at one time. And then, who is
this for? Cuz it can't be for you, you
know? Like, obviously, everything you
work on should be fulfilling and
exciting and interesting to you, but
you're not
the customer of your product, by
definition, right? You can't buy it from
yourself. So, like,
how is this going to provide value for
the audience? That's like the most
important thing, and and that has to be
the ruthless test that you
check everything you're doing against.
Number three is like, who are the people
that are helping you check whether
you're doing that or not, right? And so,
I think you need to have that test, even
if you're self-funding an
entrepreneurial venture. Like,
the fact that, you know, you were
successful in the past, so you don't
have to get venture capital on your next
project, that's great, but it's also a
potential disadvantage because now you
don't have this external objective
feedback telling you where you can
improve, where you can fall short. So,
that means you need to work extra hard
to cultivate those people, whether it's
a board of directors, whether it's
trusted friends, whether it's a a focus
group. Like, who is interacting with
this thing and giving you feedback? I
think that's really important. And then
I would say the fourth, and the most
important one,
and this is where ego, I think, kills a
lot of projects, is people think like,
"If I build it, they will come." Right?
If I just make something so good, it
will automatically be successful. Or
they go, "I'm a maker. Like, I shouldn't
have to also be a marketer." And and to
me, the creative process, the
entrepreneurial process, is sort of two
consecutive marathons. So, you run this
marathon, you you make a book, you know,
you you have a movie in the can, you
have a a prototype of an invention,
whatever it is,
you you know, you stagger across the
finish line, and you're like, "I did
it." And like, you know, the race
proctor, they grab you, and you think
they're taking you to the metal stand.
They're like, "You know, you did it. You
won." Uh but really, they're just like
taking you through a chute to the
starting line of the second marathon,
which is now how the hell do we get this
into people's hands, right? And so, with
every book, it's like the first marathon
is making it for me, and then the second
marathon is like, "All right, now I have
to be as creative, I have to work as
hard, I have to throw as much energy
into selling this thing to everyone that
it's potentially for as humanly
possible." And so, I tend to find that
creatives are either uh with books or
movies or what whatever I'm working on,
is either they're only interested in the
marketing marathon cuz they're great
sales people and they think like oh I'll
just slap something together or they're
so creative and they so love that
process that they want to
they want to skip the second marathon.
What does success look like for you? So
we started with that, sure, you know,
that you have to have that clarity. Like
in in life, what is success?
For me, success is a couple things. I
think it's to have the creative freedom
to make the things that I feel
compelled to make and produce. Having
the sort of lifestyle and personal
freedom to set up my life how I how I
want it to be, right? So to not be oh
I've got to go to Cleveland tomorrow for
this thing that I don't want to go like
I don't I want to have that freedom. And
then um I think success is also getting
better. Like I I love books. I love
writing. I've dedicated my life to this
craft and I want to be like one of the
best people to do it. And so success is
am I moving up in my abilities? Like is
every book, regardless of sales, is it
better than the one that came before?
That's a that's also one of my
definitions of success.
All right. And before I ask my last
question, where can these guys find you?
@ryanholiday on pretty much every social
platform and then my website's
ryanholiday.net.
And then the books are everywhere books
are sold.
Nice.
Yeah.
All right. So final question. What's the
impact that you want to have on the
world?
This is part of my definition of
success, obviously, is is to have
impact. I think my impact is I I want to
write things and come up with ideas and
communicate sort of stories and
connections from history
that give people
the that that that answer that question
that we started with talking about,
which is like how do you live? You know,
what how do you get to the good life?
I'm I'm trying to make the things that I
wished that were there for me, but that
if they weren't there for me, I can make
them for other people. So, like when
someone says, you know, like this book
changed my life, or when someone says, I
don't read, but I read your book. That's
the kind of impact. So, I'm I'm trying
to have impact with people that I feel
like are maybe not well served by the
existing things in the in the market.
So, I'm trying to
You know, I'm trying to make uh books
that that that help people with life,
you know? That That's a That's a an easy
thing to say, it's a hard thing to do,
but I feel like I'm chipping away at it.
The front that people present, the way
they look, the way they talk to us,
their words,
we sort of take it face value.
And although we might think, or we might
know from reading a book or whatever,
that you can't always trust appearances
is kind of a cliché, we can't control
ourselves.
So, it makes