Stoicism 101: A Practical Guide for Entrepreneurs


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.”

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 Deities, 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, 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 miscontrued 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.”



“‘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 who 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 – that 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.”



“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:
(Note 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)

Have you seen?
Tim Ferriss on TechCrunch’s Crunchbase
Tim Ferriss on Google Profiles
Tim Ferriss on MySpace

Posted on: April 13, 2009.

Watch The Tim Ferriss Experiment, the new #1-rated TV show with "the world's best human guinea pig" (Newsweek), Tim Ferriss. It's Mythbusters meets Jackass. Shot and edited by the Emmy-award winning team behind Anthony Bourdain's No Reservations and Parts Unknown. Here's the trailer.

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341 comments on “Stoicism 101: A Practical Guide for Entrepreneurs

  1. “Is this what I used to dread?”

    I think this quotation is worth it's weight in gold. When you are pursuing something big – as an entrepreneur does – it seems like every bump in the road and every barrier or setback bears your ultimate doom. In retrospect, most of these perceived disasters either turn out to be little more than annoyances or even opportunities. I've often found it helpful, when in the thick of it, to think about “how bad can it really be?” By playing out the worst case scenario, it's possible to diffuse the fear of the situation and concentrate on the opportunity.

    Thanks for a great post. I've been reading Tim mention Seneca for some time now. Perhaps now is the time to pick up some of his writing.



  2. There's a certain appeal to Stoicism; especially to me and others like me: more and more connected-yet-distanced from each other.

    I appreciate your write-up and how you connect this philosophy with modern life, yet I'm also glad that few of my friends are full-blooded Stoics.


  3. I co-majored in philosophy and stoicism was one of my favorite philosophies because it is a practical application with uses in any situation. My experience is that most people do not react well to a stoic take on seemingly unfortunate events. Most people look at it as inconsiderate but really its just the best way. My other favorite philosophy is Socrates' dialogues. His philosophy about death is great: 'if there is a heaven I was a good man, and if there isnt and it is just a long sleep then I welcome that too' paraphrased. Thanks for the late night post, and the site update for mobile.


  4. Tim has often referred to Seneca and, being unfamiliar with his writings, I never quite understood why? Now its all very clear. There are so many parallels between the Stoic philosophy and Tim's approach to life in 4HWW and beyond.

    I'm not religious. I don't follow a creed or doctrine. But the Stoic philosophy appeals greatly.

    Great post. Brilliant information.

    Thx Ryan and Tim.


  5. Hey Tim,

    I took your advice and brought Seneca with me on a mini retirement to Greece. It was life changing. Our society seems to have shifted into books like the Secret that just don't seem to posses the depth and practical applications that these principals do. Great work.



  6. Thanks Tim and Ryan for giving me (and I'm sure countless others) the impetus to further explore the Stoics. Have added your suggestions to wishlist for next order and must read bookmarks.

    “It is not death that a man should fear, but he should fear never beginning to live.” – Marcus Aurelius


  7. I am currently reading Letters of a Stoic, on Letter XL. I underline about 2-3 phrases per section. One of my favorites so far is

    “'Any man', he says, 'who does not think that what he has is more than ample, is an unhappy man, even if he is the master of the whole world.'”


  8. When I took Philosophy in college the professor never framed the message in a way I found practical for business and in turn I never found philosophy very appealing. Turning negatives into positives is a huge concept for budding entrepreneurs as there are a lot of ups and downs in building a business. I think every person who is getting beat down by entrepreneurship should read both this post as well as the one on emotional highs and lows.

    Thanks Tim and Ryan for putting an entrepreneurial spin on Stoicism for us!


  9. People interested in stoicism would do well to check out “A Guide To the Good Life: The Ancient Art Of Stoic Joy” by William Irvine, which provides an effective primer like this article, gives you the history of many of the stoics mentioned, and provides stoic philosophers views on things common in daily life. It's the most useful book I've ever read.

    I think one of the things I've gotten out of stoicism, and something that people often forget about stoicism, is that stoics have a duty to society, and that it is everybody's obligation to figure out what they're best at and then do the sh*t out of it. I think that right there is the basis for entrepreneurialism.


  10. Doesn't everyone think like this naturally? Does it have to be a specific mindset?

    Tim/Ryan, was your real world example a showcase of your own self barriers? Why does “remember you're small” bother you? I think it's important to remember where you're going and what your goals are, and to observe where you currently are given the gravity of your goal… and if you're always thinking big, aren't you going to always remember that you're small? That works!

    This trick is it being non-linear, doing it all at once and that both excites and humbles you.

    There is no right/wrong there are just opinions given ones perception, or popular opinion based upon time and place.

    I guess my observation is do what works for you and create the rules as you go along.


  11. Also, another tip:

    There are just things happening in the world – nothing else. People just add meaning and stories to situations, when the truth is, it just happened. It is difficult for people to accept this concept for sensitive situations, though, when you boil it down, strip away all added-meaning and story.. it's just something that happened.

    I think a part of using that concept and living in this society is marrying the thought with human empathy. It doesn't ''mean'' that you look at everything and are 'cold' towards it, just that you should understand the base 'truth' of what happened – which is always just an action; all the while connecting, listening to and understanding the vast majority of people who don't look at what happened with the same concept of thought.

    /end my random thoughts :p


  12. Really weird I found this today- my wife accused me of be stoic last night and I took offense- never saw myself as such, but it is true- just did not like the negative implication and bears truth to the idea that most people do perceive it as my wife put it as being a pr*ck.


  13. I am convinced that the more you attain in life the more it becomes an endless poker game..the best things are still free.

    For the ambitious there is ultimately one necessity-
    wisdom: study, practice, refine, repeat.

    Other terrific reads are The Art of War, The Prince, and An Open Heart: Practicing Compassion in Everyday Life

    Great post Tim and Ryan..the stoics were responsible for arguably the greatest empire in history …


  14. For me, Monday morning is generally set aside for reading (and, wow!), what a pleasure it was to start my day along with this post.

    In reading it, though, I was quite intrigued by how it appears to mirror certain tenets of Buddhism in many ways. . .and the core principle of seeking a certain “detachment” from life's ephemeral “problems” and our own insecurities is almost “right on” with Buddhist teachings. It's quite fascinating, actually.

    I often wonder how much of these teachings were shared across the world through explorers and traders, and how teachings that we currently attribute to one individual or region of the world have actually materialized from interaction between different peoples and geographic regions. Tim, or other folks reading. . if you know of any research in this area, could you point me in the right direction, please?

    Ryan, I'm curious as to if you've had any experience in finding ways of sharing this sort of content with people who can be somewhat averse to opening themselves up a bit to new ideas/ways of thinking. This is one of my own personal challenges, I guess. . .you see, as an entrepreneur and a guy who is always open to any new learning experience, I'm an easy sell when it comes to broadening my horizons. . .particularly with a “wee bit 'o philosophy.” But sharing this great stuff with others I find difficult, as I think a lot of people not instantly intrigued by it, find it to be preachy instead. Any insight/tips you can provide? This is also something I pointed to when Cameron posted his “Manic…” post here some months back as well. Sharing this insight with family members and team members so that they too can attempt to understand the entrepreneurial mindset is often the toughest sell.

    I'd love to hear your feedback.



    • Yes, the same thought crossed my mind in regards to the similarities of Buddhism and Stoicism. the detachment, the focus on right attitude and right actions. Underlying it all we have the notion of the impermanence of all things, how ephemeral life is. As I read the article I was struck how the two were almost interchangeable soo…good point Doc!


  15. Thanks, Tim! This is timed perfectly, as I'm feeling today as a new starting place as I move in a new direction with a number of projects. I've been feeling that my Good is getting in the way of Great right now. Seneca's ability to come face to face with the worst that could come, and laughing in the face of it is exactly what I need right now. Thanks!


  16. I would second the recommendation for Tom Wolfe's “A Man in Full”.

    I've read it numerous times, but it has been years. I will need to dig it out – thank you for the reminder.