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The Stoic Challenge

William B. Irvine

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The Stoic Challenge - William B. Irvine (Annotated).pdf (file not included in this release)

My Summary

Main Ideas, Takeaways & Similarities

  • Treating setbacks as a test—instead of emotional distress
  • Frustration -> Anger
  • Don’t attempt to get other people to be (insert negative emotion) with you. Now two people are affected and set back.
  • Chapter 3: Fantastic resilience stories
  • Resilient people never consider themselves victims.
  • Children need setbacks to be resilient
  • Negative Visualization
  • Frames: Competing obligations, incompetence, storytelling, comedic, game, stoic test
  • Acceptance
  • Stoic God as a guide
  • Stoic test: 5 seconds to declare it a test
  • Goal is anger prevention—not anger management
  • Look forward to setbacks -> Become better
    • Put self in challenging circumstances (stoic adventures)
  • You always got that 10% more you can do
  • Never allow the Lazy voice (do it tomorrow, start tomorrow) to run your life!
  • Embrace failure, do it quickly: Collect those “No”s
  • Toughness training
  • Too much comfort and pleasure turns into pain and softness
  • Death: Last-time meditation, prospective retrospection

Questions

I. What is the problem?
A. How is this problem formulated?
B. Why is this problem important?
C. What is the history of this problem?
D. Which prominent personalities have been interested in this problem?

II. What solutions to the problem are there?
A. What are the conclusions reached?
B. By what argument(s) is the conclusion reached?
C. What facts or assumptions serve as premises?
D. When a prominent personality offers a solution, does he also argue for or against other prominent personalities? Does he raise objections to alternative solutions? Does he consider objections to his own solutions?

III. Evaluation
A. What are the advantages and disadvantages of the alternative formulations to the problem?
B. Has the importance or history of the problem ever been misrepresented?
C. Are the solutions logically related to the premises?
D. Are the facts true? Are the assumptions acceptable? Are the objections answerable?

AI Summary

Here is a comprehensive summary of The Stoic Challenge by William B. Irvine (annotated edition):

Overview
William B. Irvine’s _The Stoic Challenge: A Philosopher’s Guide to Becoming Tougher, Calmer, and More Resilient_offers a modern, practical approach to Stoicism. Irvine blends the teachings of ancient Stoics like Marcus Aurelius, Seneca, and Epictetus with modern psychology, especially research on cognitive framing, to help readers turn life’s setbacks into opportunities for growth and calmness.

Core Premise

Irvine introduces the Stoic Test Strategy—a mindset where setbacks are treated as tests administered by fictional “Stoic gods” (or imagined coaches/teachers) to strengthen resilience. By reframing difficulties as challenges, individuals can reduce frustration, anger, and despair, replacing them with calm resourcefulness and even satisfaction.

Part I: Dealing with Life’s Challenges

  • Setbacks and Perspective: Life is filled with daily nuisances (burnt toast, traffic jams) and major upheavals (illness, job loss, bereavement). The emotional cost of setbacks often exceeds their physical cost. By journaling about setbacks, one can notice emotional overreactions and start minimizing them.
  • Anger as Anti-Joy: Seneca’s On Anger is central. Anger multiplies misery (contagiously affecting others) and lingers for years. Stoic practice trains one to avoid—not just suppress—anger by reframing and self-questioning.
  • Resilience Models: Irvine highlights inspiring examples, such as Neil Armstrong’s stoic calm after a near-fatal crash, Bethany Hamilton’s return to pro surfing after losing an arm, Alison Botha’s recovery and inspirational work after a brutal attack, Roger Ebert’s humor after losing his voice, Lou Gehrig’s dignified ALS acceptance, Stephen Hawking’s perseverance, and Jean-Dominique Bauby’s dictated memoir from near-total paralysis.

Part II: The Psychology of Setbacks

  • Framing Effect: Modern psychology (Kahneman & Tversky) validates the Stoic insight that how we mentally frame events shapes our emotions. Seeing setbacks as tests activates problem-solving rather than despair.
  • Anchoring & Mental Habits: People anchor expectations too high, leading to chronic frustration when life diverges from ideal scenarios. Stoic framing lowers or adjusts anchors.
  • Mind Duality: We have a rational mind capable of reframing and a reactive “first mind” prone to emotional spirals. Stoic exercises strengthen the rational mind.

Part III: Taking Stoic Tests

  • Practical Application: Treat every frustration (missed flight, rude colleague) as a Stoic test to practice patience, ingenuity, and calmness.
  • Five-Second Rule: When frustration sparks, count five seconds to consciously choose a Stoic framing before reacting.
  • Your Other Setback Challenge: Beyond enduring, Stoics train by deliberately leaving comfort zones (cold showers, fasting, voluntary discomfort) to fortify against future hardship.

Part IV: Living a Stoic Life

  • Studying for Tests: Regularly practicing discomfort and reframing makes calmness second nature.
  • Embracing “Failure”: Failures are chances to refine one’s character. A setback survived well is a victory.
  • Toughness Training: Expanding one’s comfort zone ensures fewer events feel catastrophic.
  • Setups (Positive Turns): Even windfalls can be tests (inflated ego, complacency). Stoics maintain gratitude without entitlement.
  • Death as the Final Exam: The ultimate Stoic test is facing mortality with courage, using daily practice to prepare for a calm, grateful exit.

Conclusion

Irvine emphasizes that Stoicism is not about suppressing emotions or grim endurance but about cultivating joy, calmness, and perspective despite life’s unpredictability. Setbacks, framed properly, can lead to resilience, gratitude, and a more fulfilling life.

Highlights

philosophy of life (Page 8)

If you try to live without a philosophy of life, you will find yourself extemporizing your way through your days. As a result, your daily efforts are likely to be haphazard, and your life is likely to be misspent. What a waste! (Page 8)

bunch of spoiled brats we twenty-first-century humans are. (Page 9)

Stoic test strategy: when faced with a setback, we should treat it as a test of our resilience and resourcefulness, devised and administered, as I have said, by imaginary Stoic gods. (Page 10)

rediscovered by modern psychologists, who christened it the framing effect: how we mentally characterize a situation has a profound impact on how we respond to it emotionally. (Page 11)

Their goal wasn’t to banish emotion but to minimize the number of negative emotions—such as feelings of frustration, anger, grief, and envy—that they experienced. They had nothing against the experience of positive emotions, including delight and even joy. (Page 11)

eternal optimists (Page 11)

Their goal was not to remain calm while suffering a setback but rather to experience a setback without thereby suffering. (Page 11)

Instead of experiencing a mixture of anger and anxiety, we might be surprised to discover that we are rising enthusiastically to the challenge presented by a setback. (Page 12)

One sign of maturity is a realization of the extent to which you, either intentionally or unintentionally, make life difficult for those around you. Consequently, you should keep in mind the words of Seneca: “we are bad men living among bad men; and only one thing can calm us—we must agree to go easy on one another.”1 (Page 16)

if you drew up a list of the people who have caused you setbacks, you would have to put yourself on that list, probably at the top. (Page 16)

the biggest cost by far is the emotional distress a setback triggers. (Page 18)

setback journal (Page 18)

Getting frustrated, on the other hand, often begets anger. This is unfortunate, since anger is incompatible with happiness; indeed, anger can be thought of as anti-joy. Consequently, getting frustrated in response to a setback only makes things worse. (Page 21)

In other cases, we share our anger not with the person who made us angry but with an innocent bystander. (Page 21)

I might ask a friend for advice on finding a workaround for a setback, but I would never ask—or expect—a friend to be angry or sad about my being set back. This sort of commiseration turns a setback for one person into a setback for two, (Page 22)

The Stoic philosopher Seneca understood how much harm we do by allowing ourselves to get angry. In his essay “On Anger,” he asserts, “No plague has cost the human race more.”1 Because of anger, people insult and sue each other, they divorce each other, and they hit and even kill each other. Because of anger, the nations those people live in go to war, and as a result, millions might die at the hands of people they have never even met. Cities might be reduced to rubble, and civilizations might fall. (Page 23)

avoid getting angry (Page 23)

bring along reading material to medical appointments, since doctors are so often late. (Page 23)

Neil Armstrong (Page 25)

Bethany Hamilton (Page 26)

Alison Botha (Page 28)

Tiaan Eilerd, the man who had rescued her after her assault, was there in the delivery room. His earlier encounter with Botha had inspired him to go into medicine, and he was now a doctor. (Page 29)

ROGER EBERT (Page 29)

It struck me that I, too, will someday utter my last words; indeed, there is a long-shot chance that I have already uttered them. More generally, for everything I do, there will be a last time I do it. You might think these are dark and depressing thoughts, but they can have just the opposite effect. They can help us transform our ability to speak from something we take completely for granted into what it in fact is—something remarkable and precious. (Page 30)

Lou Gehrig (Page 30)

STEPHEN HAWKING (Page 31)

Hawking’s setback had a silver lining for humanity. Many setbacks do, especially if the person set back is resilient. (Page 32)

locked-in syndrome (Page 33)

Realize that Bauby’s situation, although bad, could have been worse. Patients with total locked-in syndrome can’t even move their eyelids, making it difficult for doctors to discover that their mind is still functioning, and if it is, making it impossible to communicate with them. But such cases have a ray of hope. Technological breakthroughs have made it possible for locked-in patients to communicate with thought alone. Electrodes implanted in their brain send signals to a computer. By this means, a patient can pick out letters on a computer screen. The process is very slow, though: one woman patient was able to “type” at the rate of one or two words per minute—and felt delighted to be able to do so I have found it useful, when my word processor is balky, to contemplate her predicament. (Page 34)

Theodore Roosevelt offered this bit of Stoicinspired advice: “Do what you can, with what you’ve got, where you are.” (Page 34)

When the number of options available is limited, it is foolish to fuss and fret. We should instead simply choose the best of them and get on with life. To behave otherwise is to waste precious time and energy. (Page 35)

Consider London during the Second World War. It was subjected to regular bombings. Before the war, experts had predicted that those who were bombed would experience extreme distress and that morale would be crushed. This is one reason Hitler thought it was worth doing. But just the opposite happened. People took to heart the advice to “Keep calm and carry on.” They followed in the footsteps of their British ancestors and kept, to the best of their ability, a stiff upper lip. (Page 36)

individuals are in many cases substantially less resilient than their ancestors were. (Page 37)

One of them is arguably the 1969 publication of On Death and Dying. In this best-selling book, Elisabeth Kübler-Ross described the five stages of grief: denial, anger, bargaining, depression, and finally, acceptance. (Page 37)

boom in psychological counseling (Page 37)

PSYCHOLOGISTS WEREN’T ALONE in undermining people’s resilience. Politicians also got into the act. (Page 37)

victims. It is a label that many people are quick to accept. (Page 37)

A resilient person will refuse to play the role of victim. (Page 38)

On the advice of psychologists, parents of the 1990s and 2000s worked hard to give their children setback-free childhoods. (Page 39)

These overly protective parents also took steps to prevent their children from experiencing failure. The theory seems to have been that children who experienced lots of success would get used to succeeding and would therefore be more likely to succeed in the future. As a result, there were no longer winners and losers in competitive events; instead, everyone was a winner, so everyone got a trophy. In many schools, there were no longer failing grades; everyone who showed up for an exam got a passing grade, and everyone who stuck around for four years of high school graduated. (Page 39)

instead of regarding the failures he experiences as stepping stones on the road to eventual success, he might regard them simply as traumatic events. (Page 40)

evidence that resilience is not an innate trait; it is instead an acquired ability (Page 40)

WHEN YOU EXPERIENCE A SETBACK, your subconscious mind goes to work trying to fathom its cause, and it is inclined to point an accusing finger: it looks for another person as the cause and likes to attribute sinister motives to that person. (Page 43)

More generally, your subconscious mind tends to treat life’s setbacks as undeserved tribulations. It therefore tries to convince you that you have been wronged. Shortly thereafter—unless you take steps to prevent it—your emotions will rise in support of your subconscious mind’s interpretation of events. But whereas your subconscious mind likes to nag your conscious mind into submission, your emotions shout their demands. As a result, in the aftermath of a setback, you might, much to your surprise, find yourself shouting at the person your subconscious mind has accused. (Page 43)

YOU MAY RESENT THE ROLE that your emotions and subconscious mind play in your life. They interfere with your ability to cope with the world and thereby make your days more challenging than they need to be. You may also imagine that the ancient Stoics, being eminently rational—they were among the world’s first logicians—would have tried to extinguish the operation of the subconscious mind and throttle the emotions. But they did no such thing. (Page 44)

upside to having a subconscious mind. (Page 44)

gut moral instinct (Page 44)

creative insights. (Page 44)

ability to reason. (Page 44)

lateral thinking (Page 44)

By treating a setback as a Stoic test, we take our subconscious mind out of the setback-response loop. (Page 45)

surprising that asking the experimental subjects the over-under questions could have such an impact on their guesses about how old he was— (Page 47)

anchoring effect. (Page 47)

subject’s conscious mind lacked sufficient information to make a rational guess, but instead of admitting its ignorance, it yielded the floor to the subject’s subconscious mind, which was happy to hazard one. (Page 47)

distorted by the anchors (Page 47)

Businesses use anchoring to sell their goods and services. Suppose a clothing store has a shipment of shirts to sell, and the store manager has two retailing options. Plan A is to price the shirts at $32 each. Plan B is to price them at $40 but to have frequent 20-percent-off sales. In either case, consumers will have access to the shirts at $32, but Plan B has the psychological advantage of sinking a $40 “regular-price anchor” into shoppers’ subconscious minds. As a result, when the shirts go on sale, customers will have the impression that they are getting a $40 shirt for only $32. This impression will trigger in them a desire to purchase additional shirts, and these added sales, together with a small number of full-price sales3 at $40 per shirt, means that overall, Plan B will be substantially more profitable than Plan A. (Page 47)

periodically make a point of imagining ways in which their lives could be worse. (Page 47)

By thinking about how things could be worse, they effectively sank an anchor into their subconscious minds (not that they thought in these psychological terms). (Page 47)

negative visualization (Page 48)

we should do is periodically have flickering thoughts about how our lives and circumstances could be worse. (Page 48)

Framing (Page 50)

framing can prevent setbacks from disrupting our tranquility (Page 50)

Epictetus, “Another person will not do you harm unless you wish it; you (Page 50)

will be harmed at just that time at which you take yourself to be harmed.” (Page 51)

The competing obligations frame: Suppose someone refuses to give you something you hope to get. Your subconscious mind will likely provide a blame frame for this setback: the person in question is cheating you. As a result, you might find yourself getting angry. There are, however, other ways to explain your failure to get what you expected. The person deciding what you got may be enmeshed in a web of obligations, meaning that if she gives you what you want, she will be unable to give others what they deserve. If this is indeed the case, it would be wrong for you to get what you expected, and it would therefore be unreasonable for you to get angry for not getting it. By framing this setback as a consequence of competing obligations, you can avoid experiencing a number of negative emotions. (Page 52)

The incompetence frame: Suppose a hotel clerk loses your reservation. Yes, he may have done so on purpose, but more likely he is simply incompetent. Frame the incident as incompetence rather than malice, and the emotion you subsequently experience might be pity rather than anger. (Page 52)

The storytelling frame: When you have been set back, think in terms of the setback story you might tell in the future. It may be a story about how frustrated you were, how mean and stupid people are, and how unfair the world is. It can, in other words, be a truly boring story, the essence of which people have likely heard hundreds of times before. With a little effort on your part, though, you can “write,” with your behavior, a story that is not just interesting but potentially uplifting to those who hear it. (Page 52)

Thinking in terms of future storytelling can take much of the sting out of the setbacks you experience. (Page 52)

Epictetus even went so far as to suggest that we should take non-Stoics’ praise as a kind of reverse indicator of our progress as Stoics: “If people think you amount to something,” he said, “distrust yourself.”7 He might likewise take other people’s criticism of him as evidence that, as a practicing Stoic, he was on the right track. This sounds perverse, I know, but look at the unhappy people around you. The surest way to win their praise is to adopt and live in accordance with their values. It will then be easy for them to praise you, because by doing so, they are indirectly praising themselves. The snag, of course, is that by sharing their values you will likely end up sharing their misery. (Page 53)

The comedic frame: When someone wrongs you, keep in mind Seneca’s comment that “laughter, and a lot of it, is the right response to the things which drive us to tears!”8 He also reminded us that this technique was employed by Socrates. After someone boxed his (Page 53)

ears, Socrates responded not by getting angry but by commenting on how unfortunate it is, when we set out for a walk, that we can’t know ahead of time whether to wear a helmet (Page 54)

Lots of people respond to insults by getting angry, and the insult thereby sets them back. A better response is simply to laugh. (Page 54)

The game frame: Consider the following scenario: while you are running, someone comes up from behind and tackles you to the ground. How would you react? Given only this much information, you might instinctively place the event in a blame frame: you have been wronged and will be quite angry at the brute responsible for the attack. (Page 55)

Although getting tackled might count as a setback in the context of a rugby game, it is a setback you must shrug off if you are to play rugby effectively. Furthermore, rather than treating the tackler like a criminal, you should treat him, as long as he didn’t break any rules, as a worthy competitor on the field of play. By employing the game frame, we can take much of the sting out of events that would otherwise be traumatic. It is therefore surprising that we don’t employ this frame more often. (Page 55)

By framing a setback as a component of a game, we can dramatically reduce its emotional impact. And the game in question needn’t be a formal game like rugby; it can be an impromptu game, like the Indians’ canoe game. (Page 56)

The Stoic test frame: The last frame that we shall consider has gamelike elements: when confronted by a setback, the Stoics say, we should pretend that imaginary Stoic gods are testing us with our well-being in mind. To pass this test—and thereby win the game—we must stay calm while finding a workaround for the setback. It is a fanciful frame, to be sure, but a useful one nonetheless. (Page 56)

interpret setbacks as interesting challenges, thereby deriving a degree of satisfaction from dealing with them. (Page 57)

In parallel manner, when you experience a setback, you are faced with not one challenge but two, and the second—preventing a flood of negative emotions— (Page 60)

Notice that I didn’t say she will find a way to conceal those emotions; she will prevent them from arising, so there won’t be any negative emotions to conceal. (Page 60)

respond with feigned anger Doing this will likely achieve the results you are hoping for without making you pay the emotional price of actually getting angry. (Page 61)

righteous indignation (Page 61)

The black community was outraged and decided to boycott Montgomery’s buses. King was chosen as their primary negotiator. In this role, he had to deal with both white racists and outraged blacks. He soon found himself getting angry at people on both sides but quickly regretted (Page 61)

doing so: “I knew that this was no way to solve a problem. ‘You must not harbor anger,’ I admonished myself. ‘You must be willing to suffer the anger of the opponent, and yet not return anger. You must not become bitter. No matter how emotional your opponents are, you must be calm.’ ” (Page 62)

Social reformers are therefore wise to follow in the footsteps of Gandhi and King, and stay calm while working passionately to bring about change. (Page 62)

George Bonanno, a professor of clinical psychology at Columbia University, argues that we are much more resilient than Kübler-Ross would have us believe and are therefore much less in need of grief counseling than many psychologists recommend—and make a living providing. Indeed, his research indicates that most people, left to themselves, will rebound from an interpersonal loss, and that grief counseling can make things worse by inadvertently undermining their resilience (Page 63)

Seneca acknowledged that some grief is appropriate in its aftermath—“Nature requires from us some sorrow”—but adds that “more than this is the result of vanity.” (Page 63)

The Stoics were also aware that in some cases, the anguish a person experiences after a death is motivated more by feelings of guilt than by grief. (Page 63)

The people we love won’t be with us forever—if nothing else, our own death will deprive us of their company. The Stoics therefore recommend that we periodically make a point of reminding ourselves just how wonderful it is that the people we love are currently part of our life. Something could have happened that deprived us of their company, but it didn’t. Aren’t we lucky? (Page 63)

go directly to stage five, acceptance. (Page 63)

God, Seneca explains, hardens, reviews, and disciplines those who have won his approval and love; but those whom he seems to favor, whom he seems to spare, he is keeping soft against the misfortunes that are to come. You are wrong if you think anyone has been exempted from ill; the man who has known happiness for many a year will receive his share some day; whoever seems to have been set free from this has only been granted a delay (Page 66)

God—indeed, that he regards us as a candidate for achieving human excellence. God, says Seneca, knows that “a man needs to be put to the test if he is to gain selfknowledge” and that “only by trying does he learn what his capacities are.”2 (Page 66)

God, he says, resembles a Roman head of household who “does not pamper a good man like a favorite slave; he puts him to the test, hardens him, and makes him ready for his service.” (Page 66)

For me, the Stoic gods are a convenient fiction. (Page 68)

The second but more significant factor in grading your performance will be your emotional response to the setback. If you remain calm and collected, you will be worthy of, say, a B. If your goal is to get an A or even an A+ on the exam, though, you will have to do more than remain calm; you will have to welcome the setback and even perk up a bit on its appearance. In this respect, you need to resemble a fireman who, after years of training, is finally called on to put out a fire. At last, a chance to show his stuff! (Page 70)

The key to successfully implementing the Stoic test strategy is to act fast. (Page 72)

if we are set back, we have five seconds to declare the event to be a Stoic test. (Page 73)

Besides writing the Declaration of Independence, Thomas Jefferson wrote a document that has since become known as “Ten Rules for a Good Life.” One rule is that when someone does something that makes us angry, we should count to ten before we speak—and count to one hundred if we are very angry. The idea is that by counting to ten, our anger will have sufficiently subsided that when we do speak, we won’t blurt out something that we will later regret. Notice, by the way, that it takes about five seconds to count to ten. (Page 73)

five-second rule, by contrast, is designed to prevent anger from arising in the first place. In other words, whereas Jefferson was interested in anger management, the Stoics were interested in anger prevention. (Page 73)

We inherited our brain and its emotion-generating wiring from these ancestors. The thing to realize is that although we have added processing power to that brain, its basic wiring hasn’t changed much, and as a result, we experience many of the same emotions as they did. Our environment is, however, radically different from theirs. One of their big challenges was getting enough food to eat; one of ours is to avoid getting heart disease as a result of overindulging in cheap and readily available food. They had to worry about getting attacked by animals; we might worry about paying our bills or losing our job. Our brain, then, might be described as a computer with lots of processing power but an archaic operating system. It is our lot in life to be stuck with such a computer. (Page 75)

“On Providence,” Seneca quotes the Cynic philosopher Demetrius as saying, “Nothing seems to me more unhappy than the man who has no experience of adversity.” (Page 77)

in the absence of adversity, a wise man will become restless. (Page 77)

we can’t set ourselves back on purpose, since setbacks require the element of surprise. What we can do, however, is put ourselves into circumstances in which challenging surprises are likely to occur. (Page 78)

By dealing with them, we can improve our skill at coming up with workarounds, and at staying calm as we do so. (Page 78)

Stoic adventure. (Page 78)

put ourselves into challenging circumstances— (Page 78)

Lazy Bill. (Page 79)

I have found that the achievement of significant goals generally requires me to be able and willing to “take one more stroke,” even though I am dead tired. (Page 80)

my battle against Lazy Bill. (Page 80)

Experiment with ignoring or even reprimanding it. And ask yourself whether you really want this lowly creature, who has never accomplished anything worthy of note, running your life. (Page 80)

BY EMBARKING ON STOIC ADVENTURES, you can imbue your life with a heroic aspect, in the sense that the author Joseph Campbell had in mind. The hero’s journey, (Page 81)

call to adventure. (Page 81)

Start undertaking Stoic adventures, and you might notice a change in yourself. Formerly when you encountered a setback, you would have responded with feelings of frustration or anger. Now you might experience a little burst of delight: Ahhh! A setback to work on! And if you successfully pass the Stoic test in question, you might experience a deep sense of satisfaction. It is, as I have said, no small feat to beat the Stoic gods at their own game. (Page 81)

self-confidence will rise. (Page 81)

One way to avoid failure is to spend time and energy anticipating obstacles that can be sidestepped. There is, however, a second, far easier way to avoid failure: make a point of choosing only goals that are easy to attain. Using this strategy, though, will make it almost impossible for us to lives of achieve notable success. Indeed, when we examine accomplished individuals, we find almost without exception that they pursued goals that were difficult to attain, experienced many failures trying to attain them, and nevertheless pressed on. the (Page 82)

James Dyson (Page 82)

Margaret Mitchell’s Gone with the Wind was rejected by thirty-eight publishers before becoming one of the best-selling books of the twentieth century, and Robert Pirsig’s best-selling Zen and the Art of Motorcycle Maintenance was rejected by 121 publishers (Page 82)

Vincent Van Gogh painted 860 canvases, only one of which sold during his lifetime. His “failed” paintings are now among the best-loved and most expensive around. (Page 83)

Failure would appear to be an essential ingredient of success in the entrepreneurial world. (Page 83)

Howard Schultz (Page 83)

Kathryn Minshew (Page 83)

Abby Falik (Page 83)

Mark Zuckerberg knows this as well as anyone, and as a result his advice to employees is not “Don’t fail,” but “Fail faster.” (Page 83)

In an attempt to keep his researchers’ morale high in the midst of all this failure, Severin Schwan, CEO of Roche Holding AG, gives champagne lunches to honor research teams whose drug development efforts came up dry. His thinking: “I would argue, from a cultural point of view, it’s more important to praise the people for the nine times they fail than for the one time they succeed.” 4 (Page 84)

think of your failures as obstacles rather than setbacks. (Page 84)

Similarly, in the business world, you can deconstruct the macro-goal of raising funds for a startup into mini-goals and micro-goals. (Page 85)

collect noes. (Page 86)

You should also keep in mind that there is something much, much worse than failing to do something difficult, and that is not even attempting to do it because you feared failure. (Page 86)

Stoics realized this and made comfort zone expansion—let us refer to it as toughness training—part of their Stoic practice They made (Page 88)

a point of periodically going out of their way to do things that made them uncomfortable. (Page 89)

Before I go any further, let me clarify the difference between toughness training and Stoic adventures (see Chapter 11). We undertake Stoic adventures, such as trying to climb a mountain, so we can experience setbacks—so we can, in other words, be surprised by unpleasant events. The Stoics knew that by doing this, we would sharpen our setback-response reflexes. Then, when we experienced a setback in daily living, we would, instead of getting frustrated or angry, simply label it a Stoic test and calmly set about trying to find the optimal workaround for it. By undertaking Stoic adventures, then, we are studying for the Stoic tests that life is likely to administer. (Page 89)

When we engage in toughness training, by contrast, we aren’t hoping for our circumstances to take an unexpected turn for the worse. To the contrary, we are going out of our way to make them take a turn for the worse, so we can expand our comfort zone. (Page 89)

Negative visualization involves thinking about how things could be worse; toughness training involves causing things to be worse. (Page 89)

At each of these steps, you would have experienced fear, and at each step, the fear would have dissipated after a few repetitions. (Page 90)

Your toughness training can extend to your diet. (Page 91)

Your toughness training should have an exercise component. (Page 91)

Whereas Seneca advocated that we set aside periods to live as if we were poor, Musonius Rufus, the Stoic philosopher who handled so well his banishment to Gyaros (see Chapter 4), thought we should always live simply. At mealtimes, he said, we should learn to be satisfied with sensible amounts of simple foods. Our clothing should also be simple, and when we choose our dwelling place, we need to keep in mind that its primary purpose is to shelter us from the weather, as well as to keep out excessive heat and cold—needs that can be met, he adds, by living in a small cave. (Page 93)

This is because, as strange as it may seem, experiencing too much comfort will reduce your capacity for experiencing pleasure. As Seneca put it, “When mind and body have been corrupted by pleasure, nothing seems bearable—not because the things which you suffer are hard, but because you are soft.” (Page 94)

goddess Nemesis liked to punish extreme pride and foolish overconfidence, otherwise known as hubris. (Page 97)

Seneca warned that “Although all things in excess bring harm, the greatest danger comes from excessive good fortune: it stirs the brain, invites the mind to entertain idle fancies, and shrouds in thick fog the distinction between falsehood and truth.” (Page 98)

cautioned, though, against allowing ourselves to become overjoyed, since doing so increases our chances of being miserable when we are ultimately set back (Page 98)

Astonished, Kahneman sheepishly explained to his colleagues that the book’s appearance there was a mistake. When it stubbornly remained on the list, Kahneman modified his story: he told people that it was staying on the list only so that the Times wouldn’t have to admit to having made a mistake in putting it there in the first place It was a clever envy avoidance maneuver on his part. (Page 99)

meditation on death, (Page 100)

last-time meditation (Page 101)

there will be a last time for everything you do. (Page 101)

To last-time meditate, you periodically pause in your daily routine to reflect that no matter what you are doing, there is a chance that this is the last time you will ever do it. I (Page 101)

prospective retrospection. (Page 101)

periodically pause (Page 101)

reflect on the likelihood that at some point in the future, you will wish you could travel back in time to this very moment. (Page 101)

Some people will interpret these mortality meditations as symptoms of an unhealthy obsession with death, but Stoics would argue just the opposite. (Page 101)

In doing these meditations, you are not dwelling on death. They are momentary, impromptu exercises, and rather than being depressing, they can be curiously revitalizing. (Page 102)

By engaging in negative visualization and its variants, you can increase the chance that, instead of simply enduring the moments of your life, you savor them to the greatest extent possible and thereby increase your chances of extracting every drop of delight that your life has to offer. (Page 102)

In order to have our best chance at a good death, we must keep in mind the Stoic principle that we should not concern ourselves with things we cannot control. Doing so is a waste of time under any circumstances, but doing so in our dying days is a waste of the precious little time we have remaining: rather than fighting our imminent death, we need to embrace it. Many elderly people realize this instinctively and inform those around them that it is their time to go. (Page 105)

Although Tversky died a natural death, he had obtained drugs that would allow him to end his life quickly and painlessly, if he chose to do so. The ancient Stoics would have understood this choice. They thought that under some circumstances, suicide wasn’t just morally acceptable; it was sensible. Seneca, for example, imagined God explaining his thinking to us: “I have made nothing easier than dying. I placed life on a downward slope: if it is prolonged, only observe and you will see how short, how easy is the path that leads to freedom.”2 Dying, then, is the easy part of your Stoic exit exam; the challenge is to retain your equanimity. I should add that as long as your continued existence can help others, Stoics would regard it as cowardly to commit suicide. (Page 106)

Your goal, under such circumstances, should be to make sure that no matter when your editor publishes your novel, it will stand as a complete work—or as complete as is humanly possible. Yes, some story elements will remain unresolved, but no important business will be left undone. In (Page 106)

particular, those who helped you will have been thanked for their help, and the people you love will know of this love. There will be precious few things about the plot that you would want to change, if you had it in your power to do so. This is in part because of the choices you made but also, and more important, because you made it your business to embrace whatever life you found yourself living. (Page 107)