Stoicism 101: A Practical Guide for

Entrepreneurs
Written by Tim Ferriss Topics: Filling the Void, Mental Performance

Stoicism was born on the porch of Zeno, but it can be used in the concrete jungle.
(Photo: Blue Cinderella)

“There is nothing the busy man is less busied with than living; there is nothing harder to
learn.”
-Seneca

Few of us would consider ourselves philosophers.

Most of us can recall at least one turtleneck-wearing intellectual in college who dedicated
countless hours of study to the most obscure philosophical points of Marx or post-structural
lesbian feminism. For what? Too often, to posture as a superior intellect at meal time or over
drinks.

Fortunately, there are a few philosophical systems designed to produce dramatic real-world
effects without the nonsense. Unfortunately, they get punished because they lack the ambiguity
required for weeks of lectures and expensive textbooks.

In the last three years, I’ve begun to explore one philosophical system in particular: Stoicism.
Though my preferred Stoic writer, Lucius Seneca, I’ve found it to be a simple and immensely
practical set of rules for better results with less effort.

Ryan Holiday is 21 years old and works directly with Dov Charney as his online strategist for
American Apparel. He gets more heat, makes more high-stakes decisions, and take more risks in
a given week than most people experience in any given quarter. He also happens to be a die-hard
Stoic and incredible at putting the principles into practice…
He kindly agreed to write this piece, and I hope you find it as valuable as I do.

Stoicism 101: A Beginner’s Guide for Entrepreneurs

Author: Ryan Holiday

For those of us who live our lives in the real world, there is one branch of philosophy created just
for us: Stoicism.

It doesn’t concern itself with complicated theories about the world, but with helping us overcome
destructive emotions and act on what can be acted upon. Just like an entrepreneur, it’s built for
action, not endless debate.

When laid out in front of you, it should be instantly clear what it means. If you have to study it to
understand it, someone is probably try to pull something over on you.

Popular with the educated elite of the Greco-Roman Empire, and with thinkers like Montaigne,
John Stuart Mill and Tom Wolfe, Stoicism has just a few central teachings. It sets out to remind
us of how unpredictable the world can be. How brief our moment of life is. How to be steadfast,
and strong, and in control of yourself. And finally, that the source of our dissatisfaction lies in
our impulsive dependency on our reflexive senses rather than logic.

If this were your average introduction to philosophy, we would have to talk about how Stoicism
was started (stoa means porch, where the early followers used to hold meetings) and when it
began. I happen to think that the history of a philosophy is less interesting than its proponents
and applications. So, for a change, let’s spend our time on the latter.

Stoicism had three principle leaders. Marcus Aurelius, the emperor of the Roman Empire, the
most powerful man on earth, sat down each day to write himself notes about restraint,
compassion and humility. Epictetus endured the horrors of slavery to found his own School
where he taught many of Rome’s greatest minds. Seneca, when Nero turned on him and
demanded his suicide, could think only of comforting his wife and friends.

Stoicism differs from most existing schools in one important sense: its purpose is practical
application. It is not an intellectual enterprise. It’s a tool that we can use to become better
entrepreneurs, better friends and better people.

Stoic writing isn’t about beating up on yourself or pointing out the negative. It’s a meditative
technique that transforms negative emotions into a sense of calm and perspective.

It’s easy to gloss over the fact that Marcus Aurelius was the Roman Emperor without truly
absorbing the gravity of that position. Emperors were Dieties, ordinary men with direct access to
unlimited wealth and adulation. Before you jump to the conclusion that the Stoics were dour and
sad men, ask yourself, if you were a dictator, what would your diary look like? How quickly
could it start to resemble Kayne West’s blog?
Stoic writing is much closer Yoga session or a pre-game warm up than to a book of philosophy a
university professor might write. It’s preparation for the philosophic life - an action - where the
right state of mind is the most critical part.

Stoics practiced what are known as “spiritual exercises” and drew upon them for strength (Note
from Tim: I dislike the word “spiritual” for reasons I’ve mentioned before, but scholar Pierre
Hadot explains it’s appropriateness here).

Let’s look at three of the most important such exercises.

Practice Misfortune

“It is in times of security that the spirit should be preparing itself for difficult times; while
fortune is bestowing favors on it is then is the time for it to be strengthened against her
rebuffs.”
-Seneca

Seneca, who enjoyed great wealth as the adviser of Nero, suggested that we ought to set aside a
certain number of days each month to practice poverty. Take a little food, wear your worst
clothes, get away from the comfort of your home and bed. Put yourself face to face with want, he
said, you’ll ask yourself “Is this what I used to dread?”

It’s important to remember that this is an exercise and not a rhetorical device. He doesn’t mean
“think about” misfortune, he means live it. Comfort is the worst kind of slavery because you’re
always afraid that something or someone will take it away. But if you can not just anticipate but
practice misfortune, then chance loses its ability to disrupt your life.

Montaigne was fond of an ancient drinking game where the members took turns holding up a
painting of a corpse inside a coffin and cheered “Drink and be merry for when you’re dead you
will look like this.”

Emotions like anxiety and fear have their roots in uncertainty and rarely in experience. Anyone
who has made a big bet on themselves knows how much energy both states can consume. The
solution is to do something about that ignorance. Make yourself familiar with the things, the
worst-case scenarios, that you’re afraid of.

Practice what you fear, whether a simulation in your mind or in real-life.

Then you, your company, and your employees will have little left to keep you from thinking and
acting big.

The downside is almost always reversible or transient.

Train Perception to Avoid Good and Bad

“Choose not to be harmed and you won’t feel harmed. Don’t feel harmed and you haven’t
been.”
-Marcus Aurelius

The Stoics had an exercise called Turning the Obstacle Upside Down. What they meant to do
was make it impossible to not practice the art of philosophy. Because if you can properly turn a
problem upside down, every “bad” becomes a new source of good.

Suppose for a second that you are trying to help someone and they respond by being surly or
unwilling to cooperate. Instead of making your life more difficult, the exercise says, they’re
actually directing you towards new virtues; for example, patience or understanding. Or, the death
of someone close to you; a chance to show fortitude. Marcus Aurelius described it like this: “The
impediment to action advances action. What stands in the way becomes the way.”

It should sound familiar because it is the same thinking behind Obama’s “teachable moments.”
Right before the election, Joe Klein asked Obama how he’d made his decision to respond to the
Reverend Wright scandal. He said something like ‘when the story broke I realized the best thing
to do wasn’t damage control, it was to speak to Americans like adults.’ And what he ended up
doing was turning a negative situation into the perfect platform for his landmark speech about
race.

The common refrain about entrepreneurs is that they take advantage of, even create,
opportunities. To the Stoic, everything is opportunity. The Reverend Wright scandal, a
frustrating case where your help goes unappreciated, the death of a loved one, none of those are
“opportunities” in the normal sense of the word. In fact, they are the opposite. They are obstacles.
What a Stoic does is turn every obstacle into an opportunity.

There is no good or bad to the practicing Stoic. There is only perception. You control perception.
You can choose to extrapolate past your first impression (‘X happened.’ –> ‘X happened and
now my life is over.’). If you tie your first response to dispassion, you’ll find that everything is
simply an opportunity.

Remember–It’s All Ephemeral

“Alexander the Great and his mule driver both died and the same thing happened to both.”
-Marcus Aurelius

I understand that entrepreneurs need to dream big and have unshakable faith in themselves in
order to do great things. But if recent Valleywag headlines are any example (Cisco Exec Makes
Death Threat Over $4,000 Bike), the inhabitants of start-up land can probably benefit from some
practice of humility and self control. Not that bad tempers and ego are new problems.

Alexander the Great conquered the known world and had cities named in his honor. This is
common knowledge.

Stoics would also point out that, once while drunk, Alexander got into a fight with his dearest
friend, Cleitus, and accidentally killed him. Afterward, he was so despondent that he couldn’t eat
or drink for three days. Sophists were called from all over Greece to see what they could do
about his grief, to no avail.

Is this the mark of a successful life? From a personal standpoint, it matters little if your name is
emblazoned on a map if you lose perspective and hurt those around you.

The exercise Marcus Aurelius suggests to remedy this is simple and effective:

“Run down the list of those who felt intense anger at something: the most famous, the most
unfortunate, the most hated, the most whatever: Where is all that now? Smoke, dust, legend…or
not even a legend. Think of all the examples. And how trivial the things we want so passionately
are.”

It’s important to note that “passion” here isn’t the modern usage we’re familiar with. From
Wikipedia:

One must therefore strive to be free of the passions, bearing in mind that the ancient meaning of
‘passion’ was “anguish” or “suffering”, that is, “passively” reacting to external events —
somewhat different from the modern use of the word. A distinction was made between pathos
(plural pathe) which is normally translated as “passion”, propathos or instinctive reaction (e.g.
turning pale and trembling when confronted by physical danger) and eupathos, which is the mark
of the Stoic sage (sophos). The eupatheia are feelings resulting from correct judgment in the
same way as the passions result from incorrect judgment.

The idea was to be free of suffering through apatheia or peace of mind (literally, ‘without
passion)’, where peace of mind was understood in the ancient sense — being objective or having
“clear judgment” and the maintenance of equanimity in the face of life’s highs and lows.

For those interested in browsing the Greek words used in Stoic writing that are often
mistranslated or misconstrued in English, here is a glossary of common terms.

Returning to the point of the exercise, it’s simple: remember how small you are.

For that matter, remember how small most everything is.

Remember that achievements can be ephemeral, and that your possession of them is for just an
instant. Learn from Alexander’s mistake. Be humble and honest and aware. That is something
you can have every single day of your life. You’ll never have to fear someone taking it from you
or, worse still, it taking over you.

Tim: To illustrate a few real-world examples, here is an email from me to Ryan as we were
working on this post:

Thanks, Ryan. Read it all and ran over all the material again. I think we’re getting there. The
piece should be uplifting and empowering without being defensive, so it will still take some
working, but no worries. I’ll be reading Epictetus tonight for more ideas. The part that bothers
me is the entire “Remember you’re small” bit, which doesn’t jive with start-up founders. To do
huge things, I really think you need to believe you can change the world and do so better than
anyone else in some respect. It is possible, however, to simultaneously recognize that all is
impermanent: the transient pains, bad PR, disloyal false friends, irrational exuberance, hitting #1
on the NY Times, whatever. I think it’s about not dwelling on pain and not clinging to ephemeral
happiness. Enjoy it to the fullest (this is where I disagree with some of the Stoic writings), but
don’t expect it to last forever, nor expect some single point in time to make your entire life
complete forever.

*****

Stoic writings are not arcane arguments for bespectacled professors—they are cognitive
exercises proven to center practitioners -To humble them -To keep them free and appreciative.

Stoic principles are often practiced in rehabilitation clinics with alcoholics so that coping
mechanisms don’t drive them to drink. One wouldn’t view their new perspective on life as
pessimistic or limiting; we celebrate the fact that, for their first time in their lives, they are
empowered and unburdened.

We’re all addicts in some respect, and we can all experience that same freedom.

You can be a Stoic, and joke around and have a happy life surrounded by what’s valuable to you.

In fact, that’s the ultimate goal.

Stoicism is Ideal for the Entrepreneurial Life

The Stoics were writing honestly, often self-critically, about how they could become better
people, be happier, and deal with the problems they faced. As an entrepreneur you can see how
practicing misfortune makes you stronger in the face of adversity; how flipping an obstacle
upside down turns problems into opportunities; and how remembering how small you are keeps
your ego manageable and in perspective.

Ultimately, that’s what Stoicism is about. It’s not some systematic discussion of why or how the
world exists. It is a series of reminders, tips and aids for living a good life.

Stoicism, as Marcus reminds himself, is not some grand Instructor but a balm, a soothing
ointment to an injury wherever we might have one. Epictetus was right when he said that “life is
hard, brutal, punishing, narrow, and confining, a deadly business.”

We should take whatever help we can get, and it just happens that that help can come from
ourselves.

To finish, I want to share some of my favorite Stoic reminders. Look at them as short, mental
routines to run through often. Each is a quick reset to recalibrate yourself and be happy with the
things that matter:
***

Marcus Aurelius

“So other people hurt me? That’s their problem. Their character and actions are not mine. What
is done to me is ordained by nature and what I do by my own.”

“Today I escaped from anxiety. Or no, I discarded it, because it was within me, in my own
perceptions—not outside.”

“When you wake up in the morning, tell yourself: The people I deal with today will be meddling,
ungrateful, arrogant, dishonest, jealous and surly. They are like this because they can’t tell good
from evil. But I have seen the beauty of good and the ugliness of evil and have recognized that
the wrongdoer has a nature related to my own–not of the same blood or birth, but the same mind,
and possessing a share of the divine. And so none of them can hurt me.”

“Because your own strength is unequal to the task, do not assume that it is beyond the powers of
man; but if anything is within the powers and province of man, believe that it is within your own
compass also.”

***

Seneca

“‘What progress have I made? I am beginning to be my own friend.’ That is progress indeed.
Such a people will never be alone and you may be sure he is a friend to all.”

“Show me a man who isn’t a slave; one is a slave to sex, another to money, another to ambition;
all are slaves to hope or fear. I could show you a man who has been a Consul who is a slave to
his ‘little old woman’, a millionaire who is the slave of a little girl in domestic service. And there
is no state of slavery more disgraceful than one which is self-imposed.”

“Count your years and you’ll be ashamed to be wanting and working for exactly the same things
as you wanted when you were a boy. Of this make sure against your dying day -your faults die
before you do.”

“Nothing, to my way of thinking, is a better proof of a well ordered mind than a man’s ability to
stop just where he is and pass some time in his own company.”

“Cling tooth and nail to the following rule: not to give in to adversity, never to trust prosperity
and always take full note of fortune’s habit of behaving just as she pleases, treating her as if she
were actually going to do everything that is in her power.”

***

Epictetus
“So-and-so’s son is dead
What happened?
His son is dead
Nothing else?
Not a thing.

So-and-so’s ship sank

What happened?
His ship sank.

So-and-so was carted off to prison.

What happened?
He was carted off to prison.
-But if we now add to this “He has had bad luck,” then each of us is adding this observation on
his own account”

***
Related Post:
Harnessing Entrepreneurial Manic-Depression: Making the Rollercoaster Work for You

The Stoic Reading and Resources List:

(3ote from Tim: I have bolded my favorites, the first two from Seneca)

Letters from a Stoic by Seneca

Dialogues and Letters (includes “On The Shortness of Life”) by Seneca
The Meditations (Gregory Hays translation. I strongly recommend this translation over all others.
It’s the difference between liking and hating it.)
The Inner Citadel: The Meditations of Marcus Aurelius by Pierre Hadot
Philosophy as a Way of Life: Spiritual Exercises from Socrates to Foucault by Pierre Hadot
The Stoic Philosophy of Seneca: Essays and Letters
To Philosophize is To Learn How to Die (essay) by Montaigne
Discourses and Selected Writings of Epictetus by Epictetus
An Essay on Marcus Aurelius by Matthew Arnold
An Amazing Lecture Series on Marcus Aurelius and Stoicism
A Man in Full by Tom Wolfe (Wolfe, Bonfire of the Vanities etc, wrote an epic book that is a
modern allegory of the teachings of Epictetus)
Seneca on Trial: The Case of the Opulent Stoic The Classic Journal, Vol. 61, No. 6 (1966)
Rudius Media Book Club Discussion of Stoicism (led by Ryan Holiday)