Video summary
The narrator embarks on an ambitious 50-kilometer run through Rome to physically embody the core tenets of Stoic philosophy, specifically the practice of doing hard things for their own sake rather than for external validation. Starting from his Airbnb accommodation in the city center and finishing where he began after covering 31 miles, the journey serves as a moving meditation on building an "inner citadel." As he passes significant historical sites like Hadrian's Tomb, which houses the remains of Marcus Aurelius, he reflects on how physical endurance reinforces mental resilience. The run illustrates that true strength comes from within, acting as a fortress against external chaos, much like the inner reservoir of fortitude attributed to George Washington by Thomas Paine.
Throughout the course, the runner visits landmarks that highlight the Stoic rejection of vanity and mob mentality in favor of self-mastery and virtue. He stands before Marcus Aurelius's victory column, noting that the emperor died before seeing it completed, underscoring that trophies are not for us but that the benefit is inherent in the act of overcoming difficulty. The journey continues along the ancient Appian Way, where he contemplates the passage of time and mortality, inspired by Seneca's reflections on aging trees and the relentless flow of history. Even when facing setbacks like getting lost or running behind schedule, the narrator applies Stoic principles to accept the unexpected with grace, viewing obstacles not as stoppages but as opportunities to test one's preparedness and adaptability.
The final stretch of the run reveals that the greatest challenges often occur in the last portion of any endeavor, a concept the narrator compares to the difficulty of finishing a book or project after the initial hard work is done. Drawing on Epictetus's advice to rely on internal resources rather than external circumstances, he pushes through fatigue and heat, realizing that the true measure of character is found when one keeps going past their perceived limits. The experience culminates in a profound sense of accomplishment not because of crossing a finish line for glory, but because he has proven his capability to endure hardship. Ultimately, the run reinforces the idea that life's best rewards lie on the other side of moral courage and the willingness to take risks, a lesson that directly influenced his own career transition from corporate work to writing.
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I'm going to run the furthest I've ever
run in my life. I'm going to run 50 km
through the streets of Rome, the eternal
city.
And I'm going to
pass some of the most important Stoic
sites in the world as I do it. But why?
That's the question. Why? Why am I going
to run 50 K? Because it's hard. That's
the whole point. The Stoics said that
doing hard things was good for you.
Along the run, I'm going to stop at a
dozen or so places that are not just
significant in terms of the history of
Stoic philosophy, but illustrative of
this idea of why we do hard things, what
those hard things can [music] teach us.
I'm starting at this place we booked on
Airbnb here in the center of Rome, and
I'm going to be finishing there roughly
50 km or 31 miles later. So now it's
just a question, and this is ultimately
what Stoicism is is, am I going to do
it?
>> [music]
[music]
>> So Marcus Aurelius was buried in there.
This is known as Hadrian's tomb. But I
think fittingly
after
Marcus and Antoninus and Hadrian are
buried there, It becomes a castle. It's
a castle here on the Tiber River
protecting Rome from invasion. It
becomes a citadel, which is actually one
of the most powerful images in Stoic
philosophy, the idea of the inner
citadel. Yeah, it's great to have
fortresses like this, but the real
fortress has to be inside, right? The
toughness inside, the the thing you
retreat to, the thing that protects you.
And and and when we do hard things,
[music] when we train, when we push
ourselves physically, that's what we're
doing. We're we're reinforcing, we are
building that inner citadel. And that
that inner citadel is what you draw on,
that inner reservoir of strength,
[music] what Thomas Paine said of George
Washington that it it was this cabinet
of fortitude. That's what protects us
from the things that are happening
outside. That That's what we draw on
when things are really hard. So, when
we're doing hard things, that's what
we're doing. We're developing that inner
citadel.
Look, do do we do hard things cuz we
want to impress people? Or do we do hard
things cuz we want to beat other people?
Do we do hard things cuz we want
trophies? No, that is not why. Behind me
is one of the great trophies of history.
It's Marcus Aurelius' victory [music]
column. It's what they put up in honor
of his victories in the Marcomannic War.
It's 400 ft of carvings. It
stretches almost 200 ft in the air. It's
uh it's it's a towering feat of
accomplishment literally carved in
stone. You know what? He wasn't around
to enjoy it. He died before it finished.
[music] And then in the 15th century, a
pope knocked him off and put St. Paul up
on top. And they they put a new
a new inscription at the bottom and they
wrongly attributed the victory to
someone else. Which is the point.
Trophies are not for you. You do hard
things because doing hard things is good
for you. The benefit is baked in in
having done them.
That's why I like doing challenges like
this. Not races, not competitions.
[music]
I I doing challenges where the victory
is what I get out of it.
>> [music]
>> So, the great line about this statue
from the
Soviet dissident Joseph Brodsky, he
walked up here one
early morning and he said,
"If Marcus Aurelius is antiquity,
it is we who are the ruins."
I think he's just sort of marveling at
this
great man
who 2,000 years ago in the
pages of his
journal,
he was writing notes to himself about
controlling his temper,
about getting up early, quenching his
desires, his urges,
about being kind to people,
about working hard.
And he says, "Fight to be the person
that philosophy tried to make you."
He didn't want to be imperialized. He
didn't want to be stained purple by all
the accoutrement of power,
the sycophants around him,
people worshipping him as a god.
He wanted to be good. He wanted to be
decent, which is ultimately like the
hardest thing to do in the world. Uh
especially when you were the most
powerful person in the world. I I love
I love this statue. It's worth a run
anytime you're in Rome.
You come up these big, gradual steps and
then suddenly
you're uh
you're at the top. There's also a quirk.
This statue, that's not the original.
The original's inside the Capitoline
Museum right there, but
it's a quirk of history that it even
survived.
The Christians who who had good reason
not to like Marcus
They would have destroyed this had they
known. They thought it was Constantine,
the first Christian emperor, so they
didn't destroy it. So, they kept it. So,
there were something like 25 equestrian
statues in antiquity that we know of.
All of them are gone except for this
one. This one endures.
And it's totally by accident.
There's a little bit of gallows humor in
this, too, because uh
I still have the furthest that I've ever
run to go.
There's a Stoic named Agrippinus who was
banished from Rome by the emperor for
running afoul of him. He was banished by
Nero.
And uh when he's told he's he's going to
he's going to have to leave, he just
says, "Okay, we'll have our lunch on the
road." So, that's kind of stoicism is
like
you take it all with a shrug.
Or a smile because
what are you going to do?
You got to be prepared for things to go
wrong, and they they just did. I just
got lost. I did a 1-mi loop in the wrong
direction. I not only knew something
like this would happen, I figured it
would happen right here. When we do hard
things,
we are prepared for them to be harder
than even than we are anticipating. It's
like Eisenhower said, "Plans are
worthless, but planning is everything."
For the Stoics, if you're like, "This is
all the gas I have in the tank. This is
all I'm capable of doing. I need
everything to go right." You're in a
real vulnerable position. But if you're
ready for everything to go wrong,
everything to go sideways, well, you'll
be pleasantly surprised when that
doesn't happen, and you won't be
unpleasantly surprised if it does
happen. That's what Seneca was saying,
that the unexpected blow lands heaviest.
If I was lost and disoriented and mad at
myself right now, this would be harder
than it is. But it's not so bad. I just
got to go down here, go here, and uh
we'll be good to go.
>> [music]
>> So, one thing we know about the Stoics
is that they hated the Colosseum. They
hated the violence. They hated the the
mob mentality of it. They hated the
brutality, the the mindlessness of it.
Seneca talks about how degrading and
gory and disgusting what happened in the
floor of the Colosseum was. Marcus
Aurelius supposedly would read his
philosophy or write in Meditations in
his in his box. He was obligated to be
there for work, but he didn't like it.
That's not to say that they didn't
understand the power of a good sports
metaphor.
Marcus Aurelius said, "Life isn't a
dance. It's more like a wrestling match.
You have to be dug in and ready for
sudden attacks." In another passage of
Meditations, he talks about being like
those gladiators who were torn apart,
bloody,
begging to come back the next day. He He
didn't actually mean that as a positive.
He He meant like they needed to change.
There There were that that life was
telling them something. It was It was
beating them up. It was destroying them,
and and they weren't going in the right
direction. The The point is, I think
they would have liked Theodore
Roosevelt's idea of of the man in the
arena. They didn't actually like the
arena, but they liked being the man in
the arena. They understood that life was
tough, that life was difficult, that it
was always challenging us.
So, this is Circus Maximus. The
Colosseum is obviously what people think
of when they think of Rome, but this is
where the sports happened. This was the
center of Roman athletic life. Something
like 250,000
spectators could fit in here. These
chariots would come zipping and zipping
and zipping by. And And one of the most
powerful images
in the Stoic virtues comes from here,
from Circus Maximus. The idea of
sophrosyne that the chariot racer,
sometimes you're pulling the horse back,
reining them in, sometimes you're
getting them to go faster and faster and
faster. And then the art of steering
this rickety chariot, trying to make the
tight turns. It's an incredibly
difficult sport. And so the The image of
the charioteer was emblematic for the
Stoics of the The art of the good life,
of temperance, of moderation, of
sophrosyne, which, you know, any kind of
challenge requires of you. You You have
to train, but you can't train too hard.
Overtraining causes injury. You can't
push yourself too hard. You have to pace
yourself to be able to hit your your
marks, your benchmarks, which are all of
which I'm thinking about right now. And
now I get to run a little bit on the
actual track, cuz you can come down and
do it, which is pretty incredible.
>> [music]
>> All right. Now the pavers on the uh
Appian Way start.
These are rough, man.
But it's hard to complain
about the fact that you're
running on a road that is
thousands of years old.
The stones have been here so long, they
have grooves of wagon wheels in them.
That could have been
from Marcus Aurelius. Could have been
from every emperor ever.
Could have been Seneca.
Could have been Epictetus.
Look, these stones were also worn down
by Allied jeeps and tanks when they
retook
Italy
town by town.
And then uh
you know, here we go.
We get to run along them ourselves. It's
still here.
Kind of gives you the sense
>> [music]
>> that Marcus Aurelius talked about, just
the the rhythms of history.
Just
one generation leading seamlessly into
the next, one after another.
Somewhere around here, I have a vague
sense memory of it. I was riding my bike
with my wife along the Appian Way.
We pulled over on the side. I hadn't
planned it. We were just hanging [music]
out. We've been together a long time,
and I just I just said, "Hey,
you think we should get married at some
point? This isn't a formal ask, but
it it are you seeing this go the same
direction I'm I am?"
>> [music]
>> And uh
we've been married 11 years now. You
know, when we talk about doing hard
things,
when we talk about courage, it's not
just physical stuff, but also [music]
the moral courage to put yourself out
there. Most of the things you want in
life, most of the good things in your
life, the best things [music] in your
life, are on the other side of some
little bit of moral courage.
It's like that movie where Matt Damon
says, "All it takes is 20 seconds of
courage, 20 [music] seconds of insane
bravery to change the course of your
life."
You know, it's the decision to walk
across the room and say hi to someone.
It's the decision to raise your hand and
volunteer for something. It's the
decision to hit publish on something.
It's the decision to go out for
something, to ask for that promotion, to
put your hat in the ring. It's the
decision to tell someone that you love
them, that you want to be with them.
[music] It's the decision also the
day-to-dayness of sticking with it even
when it's hard, even when you go, "What
am I doing?"
Even when it's not totally what you
imagine.
Right?
There's the doing the hard things.
There's the 20 seconds of
of insane bravery and commitment, the
leap. Then there's also the
day-to-dayness of it. And I do [music]
think that's why
exercise and physical challenges and,
you know, doing big scary things is is a
great metaphor.
All growth is a leap in the dark.
>> So this is supposedly this is Seneca's
tomb.
We don't know for certain. It's got no
inscriptions and uh
it's here on the Appian Way. I am almost
13 mi in.
Feeling pretty good. The last time I was
here
was I don't know
almost 12 13 years ago.
One of my favorite lines from Seneca's
he talks about how
he comes back to the house that he grew
up at.
And uh the trees are starting to die
around it and he wants to criticize the
caretaker for not taking care of them.
And the the caretaker says, "What are
you talking about? These trees were
planted when you're born. [music]
They're dying cuz they're old." And this
is when Seneca realizes that he's old.
That we can see sometimes in nature
the passing of time that is uh invisible
to us because we see ourselves in the
in the mirror each day. Uh I was looking
at a picture of myself that I took
here
12 13 years ago whenever I was here
last.
And you know, I feel the same. I feel
great. I feel better than I did then.
But but you look at it and you go, "Oh,
there's more gray hairs.
There's more wrinkles.
You could see the
the last 10 years I wouldn't say they've
been hard, but they've been a lot.
They've been a lot for all of us, right?
And so sometimes coming back to a place
that you've [music] been
is a really good reminder of that
momentum. Or there's another Stoic
concept there how we never step in the
same river twice. But the point is the
river is passing us by. And then Marcus
Aurelius talks about time being this
vicious unrelenting ceaseless almost
merciless flow of events faster and
faster and faster and it's taking
[music] us with us.
So that's what I'm
thinking about here at
Seneca's tomb. I wonder if he knew that
his plays would still be read 2,000
years later.
I wonder if he knew that his grave would
get worn down by events and eventually
forgotten.
I don't know. These are great stoic
things to think about here.
>> [music]
>> I am 15.64
in. So, this is basically the turnaround
point. [music] I'm feeling pretty good.
Feel hydrated. The shade has been nice.
It's getting hot. I'm way behind
schedule though. It's 8:40 already. So,
I'm already 3 hours and 40 minutes into
this.
I will say that the
the stopping and filming I didn't quite
budget for how much time this was going
to take, but I got some really good
advice from someone who did a run like
this before. He said, "Just let it take
however long it takes. You're You're not
going to be glad you rushed through it."
He said, "Take your time. Stop. Admire
the sights. Soak it in. If you have to
walk, you have to walk. The point isn't
to win at your hobbies. The point is to
do it. To have fun doing it. To To To
experience it. To be there for it. You
don't rush through other things that are
pleasurable. And then for some reason
physical activity we try to get done as
fast as possible. So, uh almost 16 miles
in, taking a little bit of a pause, and
then uh I'm going to turn around and go
back.
>> [music]
[music]
>> You know you're doing something crazy
when
when you think only 7 miles left.
But, that's where I am. 7 miles left.
But, that's kind of the
the good thing when you train you push
yourself
you raise your threshold higher and
higher
until what to seem like a lot
now only seems
like a little. Marcus Aurelius talks
about practice even what seems
impossible. He talks about, you know,
putting the the reins of the horse in
the opposite hands, getting practice
doing it the hard way, doing hard
things, so then
when you uh are in the middle of a hard
thing,
things that you used to think were too
hard, you actually look forward to.
I've officially done a marathon.
So, I have
5 ish or so
miles left.
My final thought as I get through the
home stretch
is this idea from Epictetus. He says um
you know, whatever difficulties you
face, understand what resources you have
inside you.
Marcus Aurelius, maybe he was riffing on
that exact passage. He would talk about
this in Meditations. He says like, "What
are you going to beat the problems of
tomorrow with?" He says the same thing
you met the problems with yesterday
with, the same weapons, the same tools.
How am I going to get through the last 6
miles? I mean,
the same
willpower and strength and training that
I got through
the first 26 miles. And And honestly,
this might This is my favorite part.
First off, cuz you know, they say it's
not really
pushing yourself until you get to your
limits. It's really
>> [music]
>> after you get tired and that point that
you keep going, that's where the sort of
the muscle and the strength and the
fortitude is earned.
But,
like when I'm working on a book, it's
like the first 2/3 I say, even the
first,
you know,
80% of it, that's the really hard part,
but it's the last 20%. It's the last
third when it's downhill, when you know
that you're going to make it as long as
you don't quit. Like, you now know that
you're you're operating under some
momentum. You've crossed most of the
difficulties off. Now, it's just Like,
some some people say, you know, the last
10%
>> [music]
>> takes 40% out of you. And that's true,
but I also think
you're in a rhythm. You you have this
sense of what you're capable of cuz of
what you've just done. And uh you just
got to see it through, which is
where I got to go now.
Well,
I did it.
Just barely.
I was dying at the end.
That was a limp across the finish line,
I'll tell you what. The limit is about
29 ooh.
The limit's about
30
exactly.
29 and a
That's where I lost it. You know they
say um
it always takes longer than you expect.
Even when you take this law into
account. [music]
I don't I mean it took much longer than
I thought.
So it is much hotter than I thought.
Thus the intersection of
it all.
My son ran the last
quarter mile with me.
Which is just the [music] best.
The fact I asked my wife if she
wanted to get married
somewhere along the Appian Way and then
all these years later
I'm finishing a run on
partly on that road.
My son is finishing with me.
I'm a very lucky person.
And now I have a slightly better sense
of what I'm capable of
and what I got in the tank.
And now uh
now I got to rest.
Hey Sam.
>> Mhm.
>> I'm dying.
>> Yeah.
How did this take 6 and 1/2 hours?
>> Well, that's not a very nice question,
is it?
So we started this apartment we uh
booked on Airbnb this morning and
here we are 31 miles
back where we started.
It's actually pretty incredible. Look at
this um
This building was built 2,000 years ago.
>> These are all tombstones. It's kind of a
memento mori.
>> Historians would say just like the
people on the uh
on the Appian Way every single one of
these monuments
is for someone who thought they had
more time
put things off
who maybe left something on the table.
Anyway, that's what I'm that's what I've
been thinking as I I through this every
day.
But it's really been an incredible place
to stay. And it's funny because I
actually started my writing career.
First house my wife and I bought.
We would host it on Airbnb when we would
travel. And it kind of is what helped me
transition from
being a corporate person to a writer. As
we bought this house and then listed
while we were gone and then I'd work
there during the week and we'd rent it
out on the weekends. That was like how
we paid for it and that's what helped me
take the risk, the jump to do
The Obstacle Is the Way. And my
publisher was not super excited about a
book about an obscure school of ancient
philosophy, but I thought life's too
short.
They're going to pay me something, so I
might as well do it. I'll figure out a
way to make it work financially. And I
did and
all this, everything that's happened
since is on the other side of taking
that
that risk.