Stoicism 101: A Practical Guide for Entrepreneurs

“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. Through 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 principal 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

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 three from Seneca)

The Tim Ferriss Show is one of the most popular podcasts in the world with more than 900 million downloads. It has been selected for "Best of Apple Podcasts" three times, it is often the #1 interview podcast across all of Apple Podcasts, and it's been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.

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370 Replies to “Stoicism 101: A Practical Guide for Entrepreneurs”

  1. @tferriss
    Testing as requested, sir.

    BTW, have you heard of the book Unstuck? It looks like material that you would be interested in. Click my name for more info…

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  2. It's not just an exercise, it's a habit one needs to establish. Habits have a way of having their own momentum and articles like these coupled with their exercises help us get forward momentum and establish those positive habits. For that, I think you both for this and articles like it.

    Quick lament: I've been a part of starting and selling 3 companies, authored 3 books, and lots of consulting and travel (34 countries so far), making me a multi-millionaire before I was 30. Now 42 and not nearly as “rich” as I was (as-in, not feeling that joy and passion in my life), I'm reading Tim's book and realizing how far I've fallen from what I loved. My momentum of standing still is strong as I work at a large software company in Seattle getting lost in the crowd. I'm feeling the creativity re-kindled through the book and these articles. Thank you for that and keep them coming.

  3. This post is the first of yours I've read and it sparked me off in a million directions. I ended reading about covalent bonding. lol. I didn't know the first thing about molecules until today. Tks for the inspiration!

  4. One more comment. I think the interpretations of stoicism that it is about emotional reserve and a striving for placidness amidst turmoil is inaccurate or at the very least just one tiny molecule of what the original thinkers intended. Bertrand Russell criticized it because he said it meant that if we weren't happy, we had to accept not being happy. I think the hellenistic writers were alluding to the process of personal accountability and ethics. That process is a subtle one because our society and our communication habits support lack of accountability in thought, word, and action. Hence, we are trying to understand and analyze an ethical paradigm from an unethical context. To be accountable at a core level is experienced somatically utilizing cognitive processes as a tool only. The perspective that stoicism is about rising above or suppressing emotion misses the point because it is a cognitive interpretation of an emotional/somatic experience. Stoicism deserves so much more depth of critique.

  5. ‘According to nature’ you want to live? O you noble Stoics, what deceptive words these are! Imagine a being like nature, wasteful beyond measure, indifferent beyond measure, without purposes and consideration, without mercy and justice, fertile and desolate and uncertain at the same time; imagine indifference itself as a power – how could you live according to this indifference? Living – is that not precisely wanting to be other than this nature? Is not living – estimating, preferring, being unjust, being limited, wanting to be different? And supposing your imperative ‘live according to nature’ meant at bottom as much as ’live according to life’ – how could you not do that? Why make a principle of what you yourselves are and must be?’ ’Beyond Good and Evil’ by Nietzsche

    ‘It may be beneficial to consider what is often called ‘mental anguish,’ to ensure that the purely ‘painful’ elements do not distract from the analysis. A young man suffers because of the death of his bride of only 8 months. His grief is terrible because he loved her passionately; and so he suffers. Yet, if he was asked: do you wish to be relieved of you grief? he might hesitate. If it were possible for a laser to burn out of his brain precisely those cells which retained his memory of her, he might well refuse to submit to this therapy. The enormity of his grief, he may realize, simply is due to the enormity of his love. Had he not loved so much then, he would not grieve so much now. He may wish he could go back in time, or that she had not died, but even in his extremity he realizes the futility of such thinking. Thus, although he may bitterly resent his need to suffer and grieve, he would not opt to grieve at her death, for that would mean her death did not matter. Thus some kinds of suffering, such as grief, cannot be foresworn without the forfeiture of something so precious that the suffering demands acceptance.’ ‘Truth and Existence’ by Michael Gelven

    ‘If Machiavelli is right, if it is in principle impossible to be morally good and do one’s duty as this was conceived by common European, and especially Christian ethics, and at the same time build Sparta or even Periclean Athens or the Rome of the Republic or even of the Antonines. Then a conclusion of the first consequence follows: that the belief that the correct, objectively valid solution to the question of how men should live can in principle be discovered, is itself in principle not true… The idea of the world and of human society as a single intelligible structure is at the root of all the many various versions of natural law – the mathematical harmonies of the Pythagoreans, the logical ladder of Platonic Forms, the genetic-logical pattern of Aristotle, the divine Logos of the Stoics and the Christian Churches and of their secularised offshoots. The advance of the natural sciences generated more empirically conceived versions of this image as well as anthropomorphic similes: of Dame Nature as an adjuster of conflicting tendencies (as in Hume or Adam Smith), of Mistress Nature as the best way to happiness (as in the works of some French Encyclopaedists) … This unifying monistic pattern is at the very heart of traditional rationalism, religious and atheistic, metaphysical and scientific, transcendental and naturalistic, that has been characteristic of Western civilization. It is the rock, upon which Western beliefs and lives have been founded, that Machiavelli seems, in effect, to have split open. So great a reversal cannot, of course, be due to the acts of a single individual. It could scarcely have taken place in a stable social and moral order; many beside him, medieval nominalists and secularists , Renaissance humanists doubtless supplied their share of the dynamite…. it was Machiavelli who lit the fatal fuse. ’The Originality of Machiavelli’ in Against the Current by Isaiah Berlin

    Stoicism may be useful as a secularised version of the Protestant work ethic but without its metaphysical justifications it seem little different from nihilism to me.

  6. Great article. Funny thing is, we were talking about Stoic philosophy before this post came along.

    I have very little time ATM so I will comment only on living the misfortune part for the moment: I wholeheartedly agree with ths idea, I actually went out of my way to practice the misfortune (temporarily left my luxury downtown residence to live in a horrible trailer in the ghetto) and it has helped tremendously to overcome the comfort trap. Not to mention it gave me the motivation and energy to make progress with my business startup and get back into serious networking. It allowed me to break free of stagnation, lethargy an anxiety caused by comfort. Of course it doesn't have to be so extreme for everyone, but it was necessary for me, and it worked for me. Now I know I can survive anything and the thorns on the path are not going to stop me from getting where I want to be.

    I recommend reading moer quotes from Marcus Aurelius an Seneca for more insights 🙂

  7. I see substantial parallels between Stoicism and philosophical Taoism. Both focus on accepting what is, trying to understand the underlying reality of life and the world, and how to best make one's way in the world.

  8. Amazing article… I love the way this blog creatively combines very diverse and interesting subjects.

    Thanks for sharing

  9. AWESOME…once again, I applaud you and your efforts to share with the world the principals of your lifestyle. I am doing my best to implement as many of the suggestions as possible; having written three books myslef, I would love for sales to rise enough for me to have an automated lifestyle and allow me the freedoms you experience. I will keep you posted on my progress.

    Thank you.

  10. Just watched the Ted talk you did awhile back. If you haven't come across Dr. Montessori's genius work regarding education, I encourage you to pick up The Absorbent Mind. She developed a method to support effortless reading and writing. You might find it useful in your quest to understand the components of functional educational system. She did it all from an analytical, scientific, and compassionate place that is rare (perhaps Jane Goodall is a fair comparison). Cheers, Rebecca

  11. Loved the piece! It's a lesson in life……the good, the bad and the ugly. We can just say “Today I will be Happy”

  12. Seems that we've entered a time of 'potpourri' philosophy. It's a wonder if a person can call themselves a Stoic or Buddhist or Utilitarian if they're only taking certain aspects of those belief systems. That being said, following the philosophy of The Enchiridion would certainly land you closer to a life of zen.

  13. Tim,

    Thanks for bringing this back to mind. I read Marcus Aurelius in college (a long time ago) and remember being struck by his view of the relatedness of all people. In a practical sense, he gave much the same guidance as might be found in Christian philosophy, albeit for different reasons.

    From the quote above:

    “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, which sounds a lot like “Forgive them, Father, for they know not what they do.”


    “…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.” Since then I have understood, “Love thy neighbor as thyself” to imply that in some sense, your neighbor IS yourself: you share the human condition (the same mind) and share a bit of the divine spark.

    I find it's easier to deal with difficult people and situations when I remember that ultimately, we are all doing the best we can and we are all connected.


  14. Hi Tim,

    We met at El Rio last Saturday. I took your advice and googled your friend Kevin and happened upon you. It was nice meeting you that night. Thanks for showing us your Michael Jackson moves!


    PS My friend didn't break his foot!

  15. Awesome-I log onto this site for the first time, and lo!-you have included a picture of the St. Francisville Inn Bed and Breakfast at the Wolf-Schlesinger House on the front page! Wow-that's reaffirming. Hope you enjoyed my hometown, if only briefly!

  16. “How much time he gains who does not look to see what his neighbor says or does or thinks, but only at what he does himself, to make it just and right.”

    – Marcus Aurelius

  17. I also recomend: Epictetus: A Stoic and Socratic Guide to Life [Paperback]
    By: A. A. Long and Thoughts of a Philosophical Fighter Pilot (Reprint ed.) [Paperback]
    By: Jim Stockdale

  18. Good posting Tim. So Seneca's your man? I like Marcus Aurelius, and a colleague pointed out to me that Epictetus lies at the source of Albert Ellis' ground-breaking work (see A Guide to Rational Living) that led to Cognitive Behavioral therapy. Ryan does a nice job of showing how the Stoics were able to put philosophy to work and actually do exercises that break you free of your mental junk. Many people these days are in a mental funk with the economy down–these thought experiments are good for giving yourself a mental tuneup and getting re-centered on your own power.

    “What then is to be done? To make the best of what is in our power, and take the rest as it naturally happens.” Epictetus, Discourses

  19. Thank you so much for writing about this. A long while ago I'd found pop self help sorely lacking (just think positively!! Why? Just because!!), so I turned to the philosophers for some REAL examination on how we should live life and why, so thanks for a) turning me on to the Stoics, which I hadn't thought of looking into, and b) for speaking to us like adults. 😉

  20. I want to write a long comment to contribute something to this but I can't think of anything, so all I have to say is…Great post!

  21. I'll take a crack.

    I will rephrase the question to be, “Can a philosopher remain happy despite torture?”

    The stoic James Stockdale, USN (1923 – 2005) answers yes.

    From “The Stoic Warrior's Triad”:

    “In a crucible like a torture prison, you reflect, you silently study what makes those about you tick. Once I had taken the measure of my torture guard, watched his eyes as he worked, watched him move,felt him move as he stood on my slumped-over back and cinched up the ropes pulling my shoulders together, I came to know that there was good in him. That was ironic because when he first came in with the new commissar when torture was instigated after I got there, I had nicknamed him “Pigeye” becauseof the total vacancy of the stare of the one eye he presented as he peeked through cell door peepholes. He was my age, balding and wiry, quick, lithe and strong, like an athletic trainer. He was totally emotionless, thus his emotionless eyes. He had almost no English-language capability, just motions and grunts. Under orders, he put me through the ropes 15 times over the years, and rebroke my bad leg once, I feel sure inadvertently. It was a court martial scene and he was having to give me the ropes before a board of North Vietnamese officers. The officers sat at a long table before Pigeye and me, and behind us was a semi-circle of soldiers bearing rifles with fixed bayonets at a kind of “dangle” position, the bayonet pointing at the cement floor ahead of them. This was in the “knobby” torture room of “New Guy Village” at Hoa Lo prison in August 1967-so-called because the walls had been crudely speckled with blobs of cement the size of an ice cream scoop in a “soundproofing” attempt. I could tell Pigeye was nervous because of these officers whom I had never seen before, and I don't think he had, and he pressed me flat over my bad leg instead of the good one he had always put the tension on before. The healing knee cartilage gave way with a loud “pop,” and the officers looked at each other and then got up and left. I couldn't get off that floor and onto my feet for nearly two months. In all those years, we probably had no more than 24 hours, one-on-one together. But neither of us ever broke the code of an unvaryingly strict “line of duty” relationship. He never tricked me, always played it straight, and I begged no mercy. I admired that in him, and I could tell he did in me. And when people say: “He was a torturer, didn't you hate him?” I say, like Solzehnitsyn, to the astonishment of,those about me, “No, he was a good soldier, never overstepped his line of duty.” By that time, I had learned that fear and guilt are the real pincers that break men's wills. I would chant under my breath as I was marched to interrogation, knowing that I must refuse to comply, and take the ropes: “Your eyes must show no fear; they must show no guilt.” The North Vietnamese had learned never to take a prisoner “downtown”-to the payoff for what our
    whole treatment regime was about-public propaganda exploitation-unless he was truly intimidated, unless they were sure he felt fear. Their threats had no meaning unless you felt fear. They had suffered the political damage of several, including myself, who had acted up, spoken up, and blurted out the truth to the hand-picked audience of foreigners at the press conference. Book IV of Discourses: “When a man who has set his will neither on dying nor upon living at any cost, comes into the presence of the tyrant, what is there to prevent him from being without fear? Nothing.”

  22. Augustine said long ago that in the great poets and philosophers of pagan antiquity he found many things that are noble and beautiful, but not among them all could he find “Come unto Me, all ye who are weary and heavy laden, and I will give you rest.”

  23. My field is in relationships – romantic relationships – and though this article seems in the realm of thought, intellect, brain power, using your mental abilities, and about business, it totally resonates with me on an emotional level. When my fears come up – nightmare flashes, triggered old stuff – I “sink in” (learned this from Rori Raye). I do my best to notice my resistance to the thing that scares me and to sink into the fear, accepting it, and then it dissolves the block – that frozen moment where I’m more focused on my fear than on what I was doing before that felt good. It’s so helped my productivity, and makes it so much easier (like the historical “coffin” exercise you mention) – to live among my fears instead of always in opposition to them. Being an entrepreneur is thrilling, and with it comes all the old garbage. Seeing everything as an opportunity is the key to everything, for me, and thank you for this post. Sincerely, Sarah

  24. Tim – just want to let you know that the main article content does not display with a white background (rather, the overall dark gray site background is shown). The light gray text on dark gray background makes it a bit tough to read – I’m using Google Chrome.

    Other than that, thanks again for all you do. You’re an inspiration to many

  25. Thanks Tim and Ryan for giving me (and I’m sure countless others) the impetus to further explore the Stoics.

  26. I was fascinated by both the original post and the lively discussion that followed.

    Thanks for giving us so much food for thought.

  27. My dad didn’t need to try tomatoes to know he didn’t like ’em. And I don’t need to read Seneca to know that Marcus Aurelius kicks his toga-covered arse.

  28. Tim,

    I thought entrepreneurs were supposed to be optimists—glass half full people.

    Stoicism seems so pessimistic—- glass at least half empty.

    Can anyone explain?

  29. What a great blog article!

    It takes Philosophy out of the ‘pure mind-games’ field to a very important application: How to live your life? I greatly appreciate the work the authors have put into this article!

    Thank you,


  30. Killer article! I always love to see people with intellect realize that practicality still matters. If I could even keep one of those ideas in mind at all time I would cause myself much less stress.



  31. Tim,

    Stoicism seems interesting…I’d be curious if you’ve read much on Taoism, as it seems a touch more poetic, but delivers the message all the same. Life is about balance, remembering that good and bad compliment each other, that beauty can’t exist without ugliness. It’s about recognizing that you can never be in balance, but you are always striving for it.

    Stay credibly and be well,


  32. Most if not all stoics sit back and wait for it to happen. Not a good attitude for enterprenuers…

  33. Just bought Epictetus’ “Enchiridion” and then stumbled on this, what a coincidence. I started wondering if his suffering made him see life in this fashion, and a monotheist in his day, go figure! It’s a great pleasure to read him.

    Fantastic link to Pierre Hadot. Indeed, “spiritual” has too many meanings and is too trite at this point, but he clears it up well, and I appreciate his approach.

    Thanks for covering all sort of things about life, Tim.

  34. Excellent article, excellent website. I had no idea so many Americans were interested in ancient philosophy. Love it, let’s spread this.

  35. Hi Tim

    I love this piece and it reminds me of something I read in a piece on Taoism.

    Remember to be like water. For there is nothing greater and survival is impossible without it, but water always returns to the lowest point it possibly can.

  36. When I first saw this article I was really interested, but I have to say I have been disappointed by it. To me it seems a little vague and contradictory.

    For example, if someone dies you should just think ‘someone has died,’ not that it is good or bad. But if we really tried to stamp out labeling things as being good or bad we would just end up as emotionless robots, and that is surely not what we want.

    I dont know, it just seems confusing to me.

  37. I found this post very useful as it addressed a lot of issues I’ve been dealing with in my own businesses. I’m really excited about this approach because it seems to most situations into pre-created/pre-planned lines of action. No need to spend time trying to figure out the same things many greater people before us have already took to solving. I can feel myself becoming more productive already! Best.

  38. Stoicism sounds the same as Buddhism, Eckhart Tolle, parts of the Bible, and things my Grandma taught me about life. Why do I have to join a fancy club of Stoics and entrepenuers just to live life with some common sense. Elevating this and writing an article about it, feeling like you’ve discovered something unique and cool that is going to make you elite, seems to me the opposite of Stoicism. Who cares if it helps your business? Business is all dust. This is about your soul.

  39. In episode 3 of “Random” you describe Seneca’s writing as being a response to a problem situation posed. Here’s my problem situation (and I’m looking for as much constructive feedback as possible). Thanks so much in advance to you and all of your readers.

    I was laid off of my job at the Philadelphia Museum of Art in February. I worked in M&PR. I’d like never to work another desk job as long as I live.

    So, in addition to having worked a couple of years in an office, I have a B.A. in Communications from Temple University (with a minor in Photography) and some experience working for smaller galleries and other non-profit organizations.

    I want to travel and work as many odd jobs as possible so that I can meet as many people as possible along the way. College has left me with $50,000 of combined credit card and student loan debt, though I’ve got plenty of unemployment to pay off bills for the next 7 months.

    What do I do???? What would someone out there do if they had over half of year of “funemployment” coming to them?

    Thanks again!


  40. Here is a great video that was inspired by this post. I hope this comment is not inappropraite but I feel that the EtchASketch analogy is perfect

  41. Tim, what do you think of Ayn Rand? I used to read her non-fiction philosopy essays back in college.

  42. I found an author, Adam Miller, who has really interesting insights on Stoic thinker, Epictetus involving non-theistic centered grace and happiness. In this article he proposes, among other things, how Epictetus enumerates how it depends on what is and is not in our control and perception. Find it here: I’d love to hear anyone’s thoughts/responses to his article or the subject here, or at my blog, especially about kenotic decentering:

    Cheers Tim for broaching life-changing purviews.


  43. In the same vein, Adam Miller explores proposals for non-theistic grace and happiness via Stoic Epictetus here. Insightful stuff. I welcome and enjoy responses to it at my site, including kenotic decentering.

  44. “Success is very ephemeral. You depend entirely on the desire of others, which makes it difficult to relax.” -Eva Green

    Hey Ryan and Tim,

    Life is simple – events are ephemeral.

    By remembering that events throughout the day are comparatively small to the rest of the world and history (and maybe universe?), you can maintain a healthy perspective to just enjoy life and live in the present moment. No need to worry or concern yourself too much over stuff.

    This isn’t to say that everything that happens in your life is meaningless and unimportant. Rather, by realizing that events around you are ultimately small, you stop being absorbed by them, gain control of your life, and can consciously focus on what’s really important to you – what makes you happy, not what “should” be important (ex. awards, status, figures).

    Nice read on Stoicism. Great reminder to keep things in perspective and be appreciative of what we do have,


  45. Great, practical advice. Tried and tested for over 2000 years, yet how relevant it remains: keep a sense of perspective, and don’t get into the habit of fearing fear itself. Face a fear head on and you’ll realise you can, more often than not, cope. Then you can get on with something more productive!

    Thanks for an engaging and educational write-up.

  46. I’d like to know your thoughts on John Stossel, a Princeton grad. He debunks myths all the time and I think if you two could speak to each other it would be interesting.

  47. Tim, I wanted to bring in a nice parallel to this post:

    In tantric yoga we have this lovely idea which is impossible until you do it and then is impossible not to do: there is no happiness and no fulfillment in any object or relationship in the world. Use that which is of the world as a lens if you wish; delight in the material but do not dwell in it. Or as the Bhagavad Gita gives it: act with skill and without attachment to the fruits of your actions.

  48. Mi nombre es natta haotzima hua ling, hola.

    Hoy es mi cumpleaños (1ro de Marzo) y estoy a punto de poner el betun de chocolate a mi pastel 🙂

    Estoy muy conmovida con usted Mr. Timothy Ferrrrrrrris (tiene un nombre especial) y con todos sus articulos, consejos, videos…

    Este articulo en especial, es algo de fantastiko y supra-especial, un muy buen regalo de cumpleaños. Usted me ha inspirado mucho y estoy agradecida.

    Voy a seguir en contacto.

    Con respeto y admiracion


  49. Tim,

    Leave it to you to make the connection between an ancient Hellenistic philosophy and entrepreneurship! But after thinking about it, it really does make sense that a philosophy that worked for emperors and statesmen like Marcus Aurelius and Senenca, with the unpredictability and stress of running ancient nations, could be appropriate for running start up companies, without getting sucked into the vortex!

    I think you should add William Irvine’s “Guide to the Good Life” to your reading list. As others have mentioned, he really does a good job of “re-animating” Stoicism for modern life. It really brought it home for me.

    One criticism that has been made of Stoicism is that in some ways it is TOO accepting of failure. Irvine points out that by emphasizing how little is withing our control or “sphere of choice”, the Stoics tended to internalize their goals. So they end up being satisfied by doing their best job, even if they fail to achieve an external objective. All they care about is fighting the good fight.

    For this reason, I think Stocism does not quite deliver the goods for serious entrepreneurs. It’s great to have the laid back attitude to a point, but you can’t survive in business if you are always accepting second (or third) best. That is why I think that Hormetism, another updated version of Stoicism, is more appealing than Irvine’s version. Hormetism has the same view about being detached, but emphasizes the need to continually train oneself to improve your chances of actually succeeding. There is some good recent stuff about this on the web.


  50. Jared

    Thanks for the heads up on Hormetism,I found the following description:

    “Hormetism vs. Stoicism. Hormetism and Stoicism both share an appreciation of the value of adversity in building character and in immunizing oneself against the distracting pull of appetites and emotions, leading to an increase in self-control and the freedom to pursue the good.

    Where Hormetism and Stocism part ways, I think, is in their view of externals. The Stoic focus on “internals” and a circumscribed “sphere of choice” looks to me like an abdication of responsibility and commitment to making positive changes in the world — including the changes to society and to oneself. While, on the face of it, Stoics seems to embrace social and personal responsibility, on looking closer, they see engagement with externals only as a way to test oneself or prove ones character. The actual outcome seems not to matter very much.

    I just cannot imagine that an emperor like Marcus Aurelius or a statesman like Seneca — much less the coach of a major league football team — would be satisfied and “rest easy” knowing that he had “done what he could do”. The view that a sincere effort is good enough, and that the actual outcome does not matter, is not a recipe for success. Some external goals are worth going all out to achieve, and some are so important that the fate of a life, an organization, or a country, depend upon them. “

  51. Great post always inspiring and practical!

    Marcus Aurelius… recommend to anyone to take time and understand this way of thinking with an open mind. You will be truly blessed

  52. Tim,

    Ive studied self help, philosophy, etc, since I was 17, I am now 22. I can say that after read this post, Ive gained more understanding and truth than all my reading from the past 5 years.

    thank you


    1. Wow — thank you so much for the comment and kind words! Ryan did a great job, and I hope we can write more on this soon…


  53. I really like the idea of rehearsing worst case scenario. I just finished a psychiatry module where we learnt about the treatment of social anxiety in cognitive behavioural therapy. Here the treatment for someone with social anxiety is a progressive ladder of practising the worst case scenarios. from sitting and imagining social interaction as step one, and the last step is walking around in public skipping or singing. One therapist would have their client walk on to a busy bus at rush our with a hand full of pennies and small change, and instead of dropping in the coin slot, the client had to drop them on the floor.The potential for creative activities is endless and apparently there is an oxford book of them, another is walking around with a banana on a leash.

  54. How Buddhist concepts parallel and surpass Stoicism for practical achievement – food for thought. [future post ideas?]

    Seeing is action. Maybe these concepts can help change how we see our world and ourselves. [hope this isn’t too formal and sermon-like. Btw, Ryan & Tim, very thought provoking, fantastic post b/c I’m Buddhist and everything written strongly resonates with my reality and life accomplishments. A rare thing. Tx.]

    1) ephemeral = “Impermanence”

    2) practicing misfortune and perception management are both detached reframing for opportunity. What’s missing? Fluid desires and understanding “Non-self”.

    3) “Unsatisfactoriness”, for detached and fluid action – happiness is momentary not lasting.

    Common ground: *Impermanence (of physical forms, perception, thought, feeling, consciousness) is the singular bedrock concept of the Buddhist nature of reality. Two more follow (Non-self, Unsatisfactoriness). All 3 are intertwined in a complex cycle called “Dependent Origination” – a fragment of which coarsely parallels CBT trigger-interpretation-response theory. While choices are (hopefully, mostly) in our control, nothing else is.

    Ryan had 2 brilliant tips: take bigger risks by actively embracing the worst outcomes and secondly, to reframe adversity into opportunity. Both require cultivating a dispassionate, detached perspective. How to do this specifically? And how can Buddhism uniquely help?

    When you reframe a situation from bad to good it really shows how our desires are very fluid. We choose what we want over time. According to Buddhism, many aspects of ourselves are changing over time – see *. Applying Impermanence to the individual, the concept of **Nonself roughly means that a person is a composite mixture of dynamic processes without a discrete, static essence (core-less onion vs peach). So what? Ever have something/someone stop being as cool/meaningful or fun as it/they used to be? Well, you can get what you want but it won’t be a lasting satisfaction. It won’t really make you “happy”. Why? Even if it’s the same, you’re changing – constantly. Leverage that in “bad” situations. If you can’t change that something, then change yourself. Find a desirable possibility in anything and I think you’re on your way to an attitude of abundance. Very useful.

    *** Unsatisfactoriness: lasting happiness isn’t possible. What you think you want won’t really be very satisfying even if you get it because of * and ** – either it will change or you will, likely both. Sure, a desire and outcome might match up for awhile. It won’t last. Nothing does. Enjoy it more for that truth. Seek momentary happiness but know it for what it is or torture yourself chasing shadows and illusions.

    Summary: if everything is dynamic where the good can be lost, the bad can be gained, we inevitably change our minds about both, making happiness come and go, all we can do is choose wisely.

  55. Hmm… I’ll have to come back to this once in a while, it’s not ready to sink in yet, but I can see how there’s value in at least embracing part of stoicism.

    But I am questioning how it could be applied to situations/problems/personality issues that I do already face. For instance, I get jealous. Jealousy brings with it the sensation of no control, loss, fear, resentment, and depression.

    Since I don’t know how you could eliminate that through exposure, that leaves trying to turn it upside down.

    Who knows, someday I may be able to turn it into a strength, like it’s similar emotion, Envy. Where Jealousy is the fear of loss of something to another person, Envy is the desire to gain what another person has. Typically it comes with resentment, anger, etc… It’s considered a negative thing because most people get that set of emotions with it, which leads them to be negative. Sabotaging, bitter pricks.

    I can’t tell you when because it was a long time ago, and I don’t know how it happened… But, Envy became a strength instead of a weakness for me. It stopped carrying the usual negatives and brings a sense of curiosity, desire, excitement, and elicits thinking big.

    This is because I don’t feel envy as “Look at that jerk, why should he have XXX when I can’t?!” and instead see it as “Hey, look at what that jerk has!” (In a playful, chiding way.) “Hmm… So that’s something I want. Now how could I get it?”

    Stoicism or no; how you perceive things, and how you react to them will always make the difference in what action you take. That in turn, will decide what results you can get.

  56. Tim,

    I would love to see more blog posts about Stocism and it’s application to daily life; especially, with regard to personal ethics.

  57. Typo: “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.”

    –> “Though” should be corrected to “through.”

    Otherwise, awesome post. Thanks Tim.

  58. This is very interesting. I find this perspective on not becoming a ‘slave’ to a personal endeavor intriguing. I find myself, after reading this, subconsciously practicing most of the aforementioned routines. I find that in my personal life it is not a matter of being alone more so than it is you just have to let people go. When an individual does not want to communicate or it becomes a problem or an obstacle as you put it. I think that it could become an opportunity, but you have to know how to handle an ordeal. I am the type of individual where I just tend to ignore affliction. You cannot coerce anything. Keep calm & carry on. I definitely apply most of these practices to my lifestyle. I just never coined a term for it. I choose to live.