Book Reviews

The Obstacle Is The Way by Ryan Holiday -Book Notes, Summary, and Review

46. The Obstacle Is The Way - Ryan Holiday

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Rating: 10/10

Date of reading: 3rd – 6th of December, 2017

Description: When life becomes unbearable and things seem grim, remember that the only way around is through the problem. This needs to be a must-read for people at the age of 14-18 to prepare them for real life. 


My notes:




“What matters is that this man, known today as the last of the Five Good Emperors, sat down to write.” ( :8)

“Our actions may be impeded . . . but there can be no impeding our intentions or dispositions. Because we can accommodate and adapt. The mind adapts and converts to its own purposes the obstacle to our acting. And then he concluded with powerful words destined for maxim. The impediment to action advances action. What stands in the way becomes the way.” ( :8)

“Coming from this particular man, these were not idle words. In his own reign of some nineteen years, he would experience nearly constant war, a horrific plague, possible infidelity, an attempt at the throne by one of his closest allies, repeated and arduous travel across the empire—from Asia Minor to Syria,” ( :8)

“Egypt, Greece, and Austria—a rapidly depleting treasury, an incompetent and greedy stepbrother as coemperor, and on and on and on.” ( :9)

“What if embedded inside it or inherent in it were certain benefits—benefits only for you? What would you do? What do you think most people would do? Probably what they’ve always done, and what you are doing right now: nothing.” ( :10)

“CEO of Intel, outlined when he described what happens to businesses in tumultuous times: “Bad companies are destroyed by crisis. Good companies survive them. Great companies are improved by them.”” ( :11)

“It’s simple. Simple but, of course, not easy. This is not a book of gushing, hazy optimism.” ( :11)

“Beneath the rock were a purse of gold coins and a note from the king, which said: “The obstacle in the path becomes the path. Never forget, within every obstacle is an opportunity to improve our condition.”” ( :12)

“But run down the list of those who came before you. Athletes who were too small. Pilots whose eyesight wasn’t good enough. Dreamers ahead of their time. Members of this race or that. Dropouts and dyslexics. Bastards, immigrants, nouveaux riches, sticklers, believers, and dreamers. Or those who came from nothing or worse, from places where their very existence was threatened on a daily basis. What happened to them?” ( :13)

“carving you a path. “The Things which hurt,” Benjamin Franklin wrote, “instruct.”” ( :13)

“We’re soft, entitled, and scared of conflict. Great times are great softeners. Abundance can be its own obstacle, as many people can attest.” ( :13)

“Objective judgment, now at this very moment. Unselfish action, now at this very moment. Willing acceptance—now at this very moment—of all external events. That’s all you need. —MARCUS AURELIUS” ( :13)




“While others are excited or afraid, we will remain calm and imperturbable. We will see things simply and straightforwardly, as they truly are—neither good nor bad. This will be an incredible advantage for us in the fight against obstacles.” ( :15)

“sangfroid: unflappable coolness under pressure.” ( :16)

“Rockefeller immediately put those insights to use. At twenty-five, a group of investors offered to invest approximately $500,000 at his direction if he could find the right oil wells in which to deploy the money. Grateful for the opportunity, Rockefeller set out to tour the nearby oil fields. A few days later, he shocked his backers by returning to Cleveland empty-handed, not having spent or invested a dollar of the funds. The opportunity didn’t feel right to him at the time, no matter how excited the rest of the market was—so he refunded the money and stayed away from drilling. It was this intense self-discipline and objectivity that allowed Rockefeller to seize advantage from obstacle after obstacle in his life,” ( :16)

“”be fearful when others are greedy and greedy when others are fearful.”” ( :17)

“You will learn that this reaction determines how successful we will be in overcoming—or possibly thriving because of—them.” ( :17)

“Where one person sees a crisis, another can see opportunity. Where one is blinded by success, another sees reality with ruthless objectivity. Where one loses control of emotions, another can remain calm. Desperation, despair, fear, powerlessness—these reactions are functions of our perceptions. You must realize: Nothing makes us feel this way; we choose to give in to such feelings. Or, like Rockefeller, choose not to.” ( :17)

“We can see disaster rationally. Or rather, like Rockefeller, we can see opportunity in every disaster, and transform that negative situation into an education, a skill set, or a fortune. Seen properly, everything that happens—be it an economic crash or a personal tragedy—is a chance to move forward. Even if it is on a bearing that we did not anticipate.” ( :18)

“Choose not to be harmed—and you won’t feel harmed. Don’t feel harmed—and you haven’t been. —MARCUS AURELIUS” ( :19)

“Looking the warden in the eye, Carter proceeded to inform him and the guards that he was not giving up the last thing he controlled: himself. In his remarkable declaration, he told them, in so many words, “I know you had nothing to do with the injustice that brought me to this jail, so I’m willing to stay here until I get out. But I will not, under any circumstances, be treated like a prisoner—because I am not and never will be powerless.”” ( :19)

“Of course. He was furious. But understanding that anger was not constructive, he refused to rage. He refused to break or grovel or despair. He would not wear a uniform, eat prison food, accept visitors, attend parole hearings, or work in the commissary to reduce his sentence. And he wouldn’t be touched. No one could lay a hand on him, unless they wanted a fight.” ( :19)

“spent reading—law books, philosophy, history. They hadn’t ruined his life—they’d just put him somewhere he didn’t deserve to be and he did not intend to stay there. He would learn and read and make the most of the time he had on his hands. He would leave prison not only a free and innocent man, but a better and improved one. It took nineteen years and two” ( :19)

“It took nineteen years and two trials to overturn that verdict, but when Carter walked out of prison, he simply resumed his life. No civil suit to recover damages, Carter did not even request an apology from” ( :19)

“the court. Because to him, that would imply that they’d taken something of his that Carter felt he was owed. That had never been his view, even in the dark depths of solitary confinement. He had made his choice: This can’t harm me—I might not have wanted it to happen, but I decide how it will affect me. No one else has the right.” ( :20)

“They can throw us in jail, label us, deprive us of our possessions, but they’ll never control our thoughts, our beliefs, our reactions. Which is to say, we are never completely powerless.” ( :20)

“As for us, we face things that are not nearly as intimidating, and then we promptly decide we’re screwed. This is how obstacles become obstacles.” ( :20)

“Or, with a shift in perception, it can be exactly what you were looking for—the chance to pierce through defenses and teach a lesson that can be learned only by experience. A mistake becomes training. Again, the event is the same: Someone messed up. But the evaluation and the outcome are different. With one approach you took advantage; with the other you succumbed to anger or fear.” ( :20)

“lysses S. Grant once sat for a photo shoot with the famous Civil War photographer, Mathew Brady. The studio was too dark, so Brady sent an assistant up to the roof to uncover a skylight. The assistant slipped and shattered the window. With horror, the spectators watched as shards of glass two inches long fell from the ceiling like daggers, crashing around Grant—each one of them plenty lethal. As the last pieces hit the ground, Brady looked over and saw that Grant hadn’t moved. He was unhurt.” ( :22)

“That’s nerve. But back in our lives . . . We are a pile of raw nerves.” ( :22)

“Like: I refuse to acknowledge that. I don’t agree to be intimidated. I resist the temptation to declare this a failure. But nerve is also a matter of acceptance: Well, I guess it’s on me then. I don’t have the luxury of being shaken up about this or replaying close calls in my head. I’m too busy and too many people are counting on me.” ( :23)

“Would you have a great empire? Rule over yourself. —PUBLIUS SYRUS” ( :24)

“When people panic, they make mistakes. They override systems. They disregard procedures, ignore rules. They deviate from the plan. They become unresponsive and stop thinking clearly.” ( :24)

“Uncertainty and fear are relieved by authority. Training is authority. It’s a release valve. With enough exposure, you can adapt out those perfectly ordinary, even innate, fears that are bred mostly from unfamiliarity. Fortunately, unfamiliarity is simple to fix (again, not easy), which makes it possible to increase our tolerance for stress and uncertainty.” ( :24)

“fluctuate. The Greeks had a word for this: apatheia. It’s the kind of calm equanimity that comes with the absence of irrational or extreme emotions.” ( :25)

“If an emotion can’t change the condition or the situation you’re dealing with, it is likely an unhelpful emotion. Or, quite possibly, a destructive one. But it’s what I feel. Right, no one said anything about not feeling it.” ( :25)

“Does what happened keep you from acting with justice, generosity, self-control, sanity, prudence, honesty, humility, straightforwardness? Nope. Then get back to work!” ( :26)

“phrase “This happened and it is bad” is actually two impressions. The first—”This happened”— is objective. The second—”it is bad”—is subjective.” ( :27)

“The perceiving eye is weak, he wrote; the observing eye is strong. Musashi understood that the observing eye sees simply what is there. The perceiving eye sees more than what is there. The observing eye” ( :27)

“observing and perceiving. The perceiving eye is weak, he wrote; the observing eye is strong. Musashi understood that the observing eye sees simply what is there. The perceiving eye sees more than what is there. The observing eye sees events, clear of distractions, exaggerations, and misperceptions. The perceiving eye sees “insurmountable obstacles” or “major setbacks” or even just “issues.” It brings its own issues to the fight. The former is helpful, the latter is not.” ( :27)

“pictetus told his students, when they’d quote some great thinker, to picture themselves observing the person having sex. It’s funny, you should try it the next time someone intimidates you or makes you feel insecure. See them in your mind, grunting, groaning, and awkward in their private life—just like the rest of us. Marcus Aurelius had a version of this exercise where he’d describe glamorous or expensive things without their euphemisms—roasted meat is a dead animal and vintage wine is old, fermented grapes. The aim was to see these things as they really are, without any of the ornamentation.” ( :28)

“Something that’s present when we deal with our own obstacles is always missing when we hear other people’s problems: the baggage. With other people we can be objective.” ( :28)

“Man does not simply exist but always decides what his existence will be, what he will become the next moment. By the same token, every human being has the freedom to change at any instant. —VIKTOR FRANKL” ( :29)

“Seth Godin, author and entrepreneur, refers to as the “tyranny of being picked.” Everything changed for Clooney when he tried a new perspective. He realized that casting is an obstacle for producers, too—they need to find somebody, and they’re all hoping that the next person to walk in the room is the right somebody. Auditions were a chance to solve their problem, not his.” ( :30)

“John wouldn’t accept that. Was there anything that could give him a shot to get back on the mound? It turns out there was. The doctors suggested an experimental surgery in which they would try to replace the ligament in his pitching elbow with a tendon from his other arm. What are the chances of me coming back after this surgery? One in one hundred. And without it? No chance, they said. He could have retired. But there was a one in one hundred chance. With rehab and training, the opportunity was partially in his control. He took it. And won 164 more games over the next thirteen seasons. That procedure is now famously known as Tommy John surgery.” ( :31)

“God, grant me the serenity to accept the things I cannot change The courage to change the things I can, And the wisdom to k now the dif f erence.” ( :32)

“What is up to us, what is not up to us. And what is up to us? Our emotions Our judgments Our creativity Our attitude Our perspective Our desires Our decisions Our determination” ( :32)

“we chase is the one that makes us think we can change things that are simply not ours to change. That someone decided not to fund your company, this isn’t up to you. But the decision to refine and improve your pitch? That is. That someone stole your idea or got to it first? No. To pivot, improve it, or fight for what’s yours? Yes.” ( :33)

“In fact, half the companies in the Fortune 500 were started during a bear market or recession. Half.” ( :35)

“Genius is the ability to put into effect what is in your mind. There’s no other definition of it. —F. SCOTT FITZGERALD” ( :36)

“This is radically different from how we’ve been taught to act. Be realistic, we’re told. Listen to feedback. Play well with others. Compromise. Well, what if the “other” party is wrong? What if conventional wisdom is too conservative? It’s this all-too-common impulse to complain, defer, and then give up that holds us back.” ( :37)

“Only then were the Allies able to see the opportunity inside the obstacle rather than simply the obstacle that threatened them. Properly seen, as long as the Allies could bend and not break, this attack would send more than fifty thousand Germans rushing headfirst into a net—or a “meat grinder,” as Patton eloquently put it.” ( :38)

“It’s one thing to not be overwhelmed by obstacles, or discouraged or upset by them. This is something that few are able to do. But after you have controlled your emotions, and you can see objectively and stand steadily, the next step becomes possible: a mental flip, so you’re looking not at the obstacle but at the opportunity within it. As Laura Ingalls Wilder put it: “There is good in everything, if only we look for it.”” ( :39)

“Blessings and burdens are not mutually exclusive. It’s a lot more complicated. Socrates had a mean, nagging wife; he always said that being married to her was good practice for philosophy.” ( :40)

“Psychologists call it adversarial growth and post-traumatic growth. “That which doesn’t kill me makes me stronger” is not a cliché but fact.” ( :40)

“rude or disrespectful: They underestimate us. A huge advantage.” ( :40)

“—conniving: We won’t have to apologize when we make an example out of them. —critical or question our abilities: Lower expectations are easier to exceed. —lazy: Makes whatever we accomplish seem all the more admirable.” ( :40)

“roblems are rarely as bad as we think—or rather, they are precisely as bad as we think. It’s a huge step forward to realize that the worst thing to happen is never the event, but the event and losing your head.” ( :42)




“here was little evidence that Demosthenes was destined to become the greatest orator of Athens, let alone all of history. He was born sickly and frail with a nearly debilitating speech impediment. At seven years old, he lost his father. And then things got worse. The large inheritance left to him—intended to pay for tutors and the best schools—was stolen by the guardians entrusted to protect him. They refused to pay his tutors, depriving him of the education he was entitled to. Still weak and sick, Demosthenes was also unable to distinguish himself in the other critical sphere of Greek life: the floor of the gymnasia. Here was this fatherless, effeminate, awkward child who no one understood, who everyone laughed at. Not exactly the boy you’d expect would soon hold the power to mobilize a nation to war by his voice alone.” ( :44)

“Demosthenes locked himself away underground—literally—in a dugout he’d had built in which to study and educate himself. To ensure he wouldn’t indulge in outside distractions, he shaved half his head so he’d be too embarrassed to go outside. And from that point forward, he dutifully descended each day into his study to work with his voice, his facial expressions, and his arguments.” ( :44)

“Demosthenes eventually won. Only a fraction of the original inheritance remained, but the money had become secondary. Demosthenes’s reputation as an orator, ability to command a crowd and his peerless knowledge” ( :45)

“Sure, Demosthenes lost the inheritance he’d been born with, and that was unfortunate. But in the process of dealing with this reality, he created a far better one—one that could never be taken from him. But you, when you’re dealt a bad hand. What’s your response? Do you fold? Or do you play it for all you’ve got?” ( :45)

“We’ve all done it. Said: “I am so [overwhelmed, tired, stressed, busy, blocked, outmatched].” And then what do we do about it? Go out and party. Or treat ourselves. Or sleep in. Or wait. It feels better to ignore or pretend. But you know deep down that that isn’t going to truly make it any better. You’ve got to act. And you’ve got to start now.” ( :45)

“along the lines of: We have someone willing to fund the first female transatlantic flight. Our first choice has already backed out. You won’t get to actually fly the plane, and we’re going to send two men along as chaperones and guess what, we’ll pay them a lot of money and you won’t get anything. Oh, and you very well might die while doing it. You know what she said to that offer? She said yes.” ( :47)

“In the first years of World War II, there was no worse assignment for British troops than being sent to the North African front. Methodical and orderly, the British hated the grueling weather and terrain that wreaked havoc on their machines and their plans. They acted how they felt: slow, timid, cautious.” ( :48)

“While you’re sleeping, traveling, attending meetings, or messing around online, the same thing is happening to you. You’re going soft. You’re not aggressive enough. You’re not pressing ahead. You’ve got a million reasons why you can’t move at a faster pace. This all makes the obstacles in your life loom very large.” ( :48)

“He says the best way out is always through And I agree to that, or in so far As I can see no way out but through. —ROBERT FROST” ( :50)

“His next move ran contrary to nearly all conventional military theory. He decided to run his boats past the gun batteries guarding the river—a considerable risk, because once down, they could not come back up. Despite an unprecedented nighttime firefight, nearly all the boats made the run unharmed. A few days later, Grant crossed the river about thirty miles downstream at the appropriately named Hard Times, Louisiana.” ( :50)

“In 1878, Thomas Edison wasn’t the only person experimenting with incandescent lights. But he was the only man willing to test six thousand different filaments—including one made from the beard hair of one of his men—inching closer each time to the one that would finally work. And, of course, he eventually found it—proving that genius often really is just persistence in disguise.” ( :51)

“And that means changing the relationship with failure. It means iterating, failing, and improving. Our capacity to try, try, try is inextricably linked with our ability and tolerance to fail, fail, fail.” ( :53)

“Great entrepreneurs are: never wedded to a position never afraid to lose a little of their investment never bitter or embarrassed never out of the game for long” ( :54)

“Remember Erwin Rommel and the quick work he made of the British and American forces in North Africa? There’s another part to that story. The Allied forces actually chose that disadvantageous battlefield on purpose. Churchill knew that they would have to take their first stand against the Germans somewhere, but to do that and lose in Europe would be disastrous for morale. In North Africa, the British learned how to fight the Germans—and early on they learned mostly by failure. But that was acceptable, because they’d anticipated a learning curve and planned for it. They welcomed it because they knew, like Grant and Edison did, what it meant: victory further down the road.” ( :54)

“It’s time you understand that the world is telling you something with each and every failure and action. It’s feedback—giving you precise instructions on how to improve, it’s trying to wake you up from your cluelessness. It’s trying to teach you something. Listen. Lessons come hard only if you’re deaf to them. Don’t be.” ( :55)

“He teaches The Process. “Don’t think about winning the SEC Championship. Don’t think about the national championship. Think about what you needed to do in this drill, on this play, in this moment. That’s the process: Let’s think about what we can do today, the task at hand.”” ( :56)

“The road to back-to-back championships is just that, a road. And you travel along a road in steps. Excellence is a matter of steps. Excelling at this one, then that one, and then the one after that. Saban’s process is exclusively this—existing in the present, taking it one step at a time, not getting distracted by anything else. Not the other team, not the scoreboard or the crowd.” ( :56)

“This was what the great nineteenth-century pioneer of meteorology, James Pollard Espy, was shown in a chance encounter as a young man. Unable to read and write until he was eighteen, Espy attended a rousing speech by the famous orator Henry Clay. After the talk, a spellbound Espy tried to make his way toward Clay, but he couldn’t form the words to speak to his idol. One of his friends shouted out for him: “He wants to be like you, even though he can’t read.” Clay grabbed one of his posters, which had the word CLAY written in big letters. He looked at Espy and said, “You see that, boy?” pointing to a letter. “That’s an A. Now, you’ve only got twenty-five more letters to go.” Espy had just been gifted the process. Within a year, he started college.” ( :57)

“How often do we compromise or settle because we feel that the real solution is too ambitious or outside our grasp? How often do we assume that change is impossible because it’s too big? Involves too many different groups? Or worse, how many people are paralyzed by all their ideas and inspirations? They chase them all and go nowhere, distracting themselves and never making headway. They’re brilliant, sure, but they rarely execute. They rarely get where they want and need to go.” ( :58)

“We are A-to-Z thinkers, fretting about A, obsessing over Z, yet forgetting all about B through Y.” ( :58)

“Another president, James Garfield, paid his way through college in 1851 by persuading his school, the Western Reserve Eclectic Institute, to let him be the janitor in exchange for tuition. He did the job every day smiling and without a hint of shame. Each morning, he’d ring the university’s bell tower to start the classes—his day already having long begun—and stomp to class with cheer and eagerness.” ( :59)

“Another president, James Garfield, paid his way through college in 1851 by persuading his school, the Western Reserve Eclectic Institute, to let him be the janitor in exchange for tuition. He did the job every day smiling and without a hint of shame. Each morning, he’d ring the university’s bell tower to start the classes—his day already having long begun—and stomp to class with cheer and eagerness. Within just one year of starting at the school he was a professor—teaching a full course load in addition to his studies. By his twenty-sixth birthday he was the dean.” ( :59)

“Only self-absorbed assholes think they are too good for whatever their current station requires.” ( :60)

“The great psychologist Viktor Frankl, survivor of three concentration camps, found presumptuousness in the age-old question: “What is the meaning of life?” As though it is someone else’s responsibility to tell you. Instead, he said, the world is asking you that question. And it’s your job to answer with your actions. In every situation, life is asking us a question, and our actions are the answer. Our job is simply to answer well.” ( :60)

“To solve the problem, United Fruit dispatched a team of high-powered lawyers. They set out in search of every file and scrap of paper in the country, ready to pay whatever it cost to win. Money, time, and resources were no object. Zemurray, the tiny, uneducated competitor, was outmatched, right? He couldn’t play their game. So he didn’t. Flexible, fluid, and defiant, he just met separately with both of the supposed owners and bought the land from each of them. He paid twice, sure, but it was over. The land was his. Forget the rule book, settle the issue.” ( :62)

“Don’t worry about the “right” way, worry about the right way. This is how we get things done. Zemurray always treated obstacles this way.” ( :62)

“he couldn’t build a bridge he needed across the Utila River—because government officials had been bribed by competitors to make bridges illegal—Zemurray had his engineers build two long piers instead. And in between which reached out far into the center of the river, they strung a temporary pontoon that could be assembled and deployed to connect them in a matter of hours. Railroads ran down each side of the riverbank, going in opposite direction. When United Fruit complained, Zemurray laughed and replied: “Why, that’s no bridge. It’s just a couple of little old wharfs.” ( :62)

“What Zemurray never lost sight of was the mission: getting bananas across the river. Whether it was a bridge or two piers with a dock in the middle, it didn’t matter so long as it got the cargo where it needed to go. When he wanted to plant bananas on a particular plantation, it wasn’t important to find the rightful owner of the land—it was to become the rightful owner. You’ve got your mission, whatever it is. To accomplish it, like the rest of us you’re in the pinch between the way you wish things were and the way they actually are (which always seem to be a disaster). How far are you willing to go? What are you willing to do about it? Scratch the complaining. No waffling. No submitting to powerlessness or fear. You can’t just run home to Mommy. How are you going to solve this problem? How are you going to get around the rules that hold you back?” ( :63)

“As Deng Xiaoping once said, “I don’t care if the cat is black or white, so long as it catches mice.” The Stoics had their own reminder: “Don’t go expecting Plato’s Republic.”” ( :63)

“Start thinking like a radical pragmatist: still ambitious, aggressive, and rooted in ideals, but also imminently practical and guided by the possible. Not on everything you would like to have, not on changing the world right at this moment, but ambitious enough to get everything you need. Don’t think” ( :63)

“small, but make the distinction between the critical and the extra. Think progress, not perfection.” ( :64)

“In a study of some 30 conflicts comprising more than 280 campaigns from ancient to modern history, the brilliant strategist and historian B. H. Liddell Hart came to a stunning conclusion: In only 6 of the 280” ( :65)

“campaigns was the decisive victory a result of a direct attack on the enemy’s main army. Only six. That’s 2 percent.” ( :66)

“They choose to exert only calculated force where it will be effective, rather than straining and struggling with pointless attrition tactics. As someone once put it after fighting Jigoro Kano, the legendary five-foot-tall founder of judo, “Trying to fight with Kano was like trying to fight with an empty jacket!” That can be you.” ( :66)

“We’re in the game of little defeating big. Therefore, Force can’t try to match Force. Of course, when pushed, the natural instinct is always to push back. But martial arts teach us that we have to ignore this impulse. We can’t push back, we have to pull until opponents lose their balance. Then we make our move.” ( :67)

“The great philosopher Søren Kierkegaard rarely sought to convince people directly from a position of authority. Instead of lecturing, he practiced a method he called “indirect communication.” Kierkegaard would write under pseudonyms, where each fake personality would embody a different platform or perspective—writing multiple times on the same subject from multiple angles to convey his point emotionally and dramatically. He would rarely tell the reader “do this” or “think that.” Instead he would show new ways of looking at or understanding the world.” ( :67)

“Believe it or not, this is the hard way. That’s why it works. Remember, sometimes the longest way around is the shortest way home.” ( :67)

“Gandhi leaned into that weakness, exaggerated it, exposed himself. He said to the most powerful occupying military in the world, I’m marching to the ocean to collect salt in direct violation of your laws. He was provoking them—What are you going to do about it? There is nothing wrong with what we’re doing—knowing that it placed authorities in an impossible dilemma: Enforce a bankrupt policy or abdicate. Within that framework, the military’s enormous strength is neutralized. Its very usage is counterproductive. Martin Luther King Jr., taking Gandhi’s lead, told his followers that they would meet “physical force with soul force.” In other words, they would use the power of opposites. In the face of violence they would be peaceful, to hate they would answer with love—and in the process, they would expose those attributes as indefensible and evil.” ( :68)

“Perhaps your enemy or obstacle really is insurmountable—as it was for many of these groups. Perhaps in this case, you haven’t got the ability to win through attrition (persistence) or you don’t want to risk learning on the job (iterate). Okay. You’re still a long way from needing to give up.” ( :68)

“ait for temporary obstacles to fizzle out. Let two jousting egos sort themselves out instead of jumping immediately into the fray. Sometimes a problem needs less of you—fewer people period—and not more.” ( :69)

“The great strategist Saul Alinsky believed that if you “push a negative hard enough and deep enough it” ( :69)

“will break through into its counterside.” Every positive has its negative. Every negative has its positive. The action is in the pushing through—all the way through to the other side. Making a negative into a positive.” ( :70)

“”physically loose and mentally tight.” For Arthur Ashe, this combination created a nearly unbeatable tennis game. As a person he’d control his emotions, but as a player he was swashbuckling, bold, and cool.” ( :71)

“Adversity can harden you. Or it can loosen you up and make you better—if you let it. Rename it and claim it, that’s what Ashe did—as have many other black athletes. The boxer Joe Louis, for example, knew that racist white boxing fans would not tolerate an emotional black fighter, so he sublimated all displays behind a steely, blank face. Known as the Ring Robot, he greatly intimidated opponents by seeming almost inhuman. He took a disadvantage and turned it into an unexpected asset in the ring.” ( :71)

“Instead of giving in to frustration, we can put it to good use. It can power our actions, which, unlike our disposition, become stronger and better when loose and bold. While others obsess with observing the rules, we’re subtly undermining them and subverting them to our advantage. Think water. When dammed by a man-made obstacle, it does not simply sit stagnant. Instead, its energy is stored and deployed, fueling the power plants that run entire cities.” ( :72)

“Everything in his life had been an obstacle, and he turned as many of his experiences as he could into openings. Why should troops or politics or mountains or Napoléon himself have been any different?” ( :72)

“To be physically and mentally loose takes no talent. That’s just recklessness. (We want right action, not action period.) To be physically and mentally tight? That’s called anxiety. It doesn’t work, either. Eventually we snap. But physical looseness combined with mental restraint? That is powerful.” ( :72)

“It’s a power that drives our opponents and competitors nuts. They think we’re toying with them. It’s maddening—like we aren’t even trying, like we’ve tuned out the world. Like we’re immune to external stressors and limitations on the march toward our goals. Because we are.” ( :72)

“This speech, known today as the “A More Perfect Union” speech, was a transformative moment. Instead of distancing himself, Obama addressed everything directly. In doing so, he not only neutralized a potentially fatal controversy but created an opportunity to seize the electoral high ground. Absorbing the power of that negative situation, his campaign was instantly infused with an energy that propelled it into the White House.” ( :73)

“What you must do is learn how to press forward precisely when everyone around you sees disaster.” ( :73)

“You always planned to do something. Write a screenplay. Travel. Start a business. Approach a possible mentor. Launch a movement. Well, now something has happened—some disruptive event like a failure or an accident or a tragedy. Use it.” ( :74)

“At certain moments in our brief existences we are faced with great trials. Often those trials are frustrating, unfortunate, or unfair. They seem to come exactly when we think we need them the least. The question is: Do we accept this as an exclusively negative event, or can we get past whatever negativity or adversity it represents and mount an offensive? Or more precisely, can we see that this “problem” presents an opportunity for a solution that we have long been waiting for? If you don’t take that, it’s on you.” ( :74)

“Great commanders look for decision points. For it is bursts of energy directed at decisive points that break things wide open. They press and press and press and then, exactly when the situation seems hopeless—or, more likely, hopelessly deadlocked—they press once more.” ( :74)

“In the meantime, cling tooth and nail to the following rule: not to give in to adversity, not to trust prosperity, and always take full note of fortune’s habit of behaving just as she pleases. —SENECA” ( :76)

“Problems, as Duke Ellington once said, are a chance for us to do our best. Just our best, that’s it. Not the impossible. We must be willing to roll the dice and lose. Prepare, at the end of the day, for none of it to work. Anyone in pursuit of a goal comes face-to-face with this time and time again. Sometimes, no amount of planning, no amount of thinking—no matter how hard we try or patiently we persist—will change the fact that some things just aren’t going to work. The world could use fewer martyrs.” ( :76)




“Try “God willing” over “the will to win” or “willing it into existence,” for even those attributes can be broken. True will is quiet humility, resilience, and flexibility; the other kind of will is weakness disguised by bluster and ambition. See which lasts longer under the hardest of obstacles.” ( :77)

“because of what he’d struggled with and learned to cope with in his own life, he was able to lead. To hold a nation, a cause, an effort, together. This is the avenue for the final discipline: the Will. If Perception and Action were the disciplines of the mind and the body, then Will is the discipline of the heart and the soul.” ( :79)

“The incomprehensible happens all the time. Certain things in life will cut you open like a knife. When that happens—at that exposing moment—the world gets a glimpse of what’s truly inside you. So what will be revealed when you’re sliced open by tension and pressure? Iron? Or air? Or bullshit?” ( :80)

“These lessons come harder but are, in the end, the most critical to wresting advantage from adversity. In every situation, we can Always prepare ourselves for more difficult times. Always accept what we’re unable to change. Always manage our expectations. Always persevere. Always learn to love our fate and what happens to us. Always protect our inner self, retreat into ourselves. Always submit to a greater, larger cause. Always remind ourselves of our own mortality. And, of course, prepare to start the cycle once more.” ( :80)

“If thy faint in the day of adversity, thy strength is small. —PROVERBS 24:10” ( :81)

“One day his father came into his room and delivered a message that would change the young boy’s life: “Theodore, you have the mind but haven’t got the body. I’m giving you the tools to make your body. It’s going to be hard drudgery and I think you have the determination to go through with it.”” ( :81)

“was to look at his father and say with determination: “I’ll make my body.” At the gym that his father built on the second-floor porch, young Roosevelt proceeded to work out feverishly every day for the next five years, slowly building muscle and strengthening his upper body against his weak lungs and for the future. By his early twenties the battle against asthma was essentially over, he’d worked—almost literally—that weakness out of his body.” ( :81)

“We take weakness for granted. We assume that the way we’re born is the way we simply are, that our disadvantages are permanent. And then we atrophy from there. That’s not necessarily the best recipe for the difficulties of life.” ( :81)

“Not everyone accepts their bad start in life. They remake their bodies and their lives with activities and exercise. They prepare themselves for the hard road. Do they hope they never have to walk it? Sure. But they are prepared for it in any case. Are you? Nobody is born with a steel backbone. We have to forge that ourselves.” ( :82)

“This is strikingly similar to what the Stoics called the Inner Citadel, that fortress inside of us that no external adversity can ever break down. An important caveat is that we are not born with such a structure; it must be built and actively reinforced. During the good times, we strengthen ourselves and our bodies so that during the difficult times, we can depend on it. We protect our inner fortress so it may protect us.” ( :82)

“The project has failed spectacularly. Tell me what went wrong?” What?! But we haven’t even launched yet . . . That’s the point. The CEO is forcing an exercise in hindsight—in advance. She is using a technique designed by psychologist Gary Klein known as a premortem.” ( :84)

“If only more people had been thinking worst-case scenario at critical points in our lifetimes, the tech bubble, Enron, 9/11, the invasion of Iraq, and the real estate bubble might have been avoidable. No one wanted to consider what could happen, and the result? Catastrophe. Today, the premortem is increasingly popular in business circles, from start-ups to Fortune 500 companies and the Harvard Business Review.” ( :84)

“”Nothing happens to the wise man against his expectation,” he wrote to a friend. “. . . nor do all things turn out for him as he wished but as he reckoned—and above all he reckoned that something could block his plans.”” ( :85)

“”What if . . .” is, It will suck but we’ll be okay. Your world is ruled by external factors. Promises aren’t kept. You don’t always get what is rightfully yours, even if you earned it. Not everything is as clean and straightforward as the games they play in business school. Be prepared for this.” ( :85)

“Beware the calm before the storm. Hope for the best, prepare for the worst. The worst is yet to come. It gets worse before it gets better.” ( :85)

“You know you want to accomplish X, so you invest time, money, and relationships into achieving it. About the worst thing that can happen is not something going wrong, but something going wrong and catching you by surprise. Why? Because unexpected failure is discouraging and being beaten back hurts.” ( :86)

“THE ART OF ACQUIESCENCE The Fates guide the person who accepts them and hinder the person who resists them. —CLEANTHES T homas Jefferson: born quiet, contemplative, and reserved—purportedly with a speech impediment. Compared to the great orators of his time—Patrick Henry, John Wesley, Edmund Burke—he was a terrible public speaker.” ( :87)

“Writing was his strength. Jefferson was the one the founding fathers turned to when they needed the Declaration of Independence. He wrote one of the most important documents in history, in a single draft.” ( :87)

“”True genius,” as the infamous Dr. Samuel Johnson once said, “is a mind of large general powers accidentally determined in some particular direction.”” ( :87)

“Let’s be clear, that is not the same thing as giving up. This has nothing to do with action—this is for the things that are immune to action. It is far easier to talk of the way things should be. It takes toughness, humility, and will to accept them for what they actually are. It takes a real man or woman to face necessity.” ( :88)

“For instance, in 2006 a long-term hip injury finally caught up with Lakers’ coach Phil Jackson, and the surgery he had to fix it severely limited his courtside movement. Relegated to a special captain’s-style chair near the players, he couldn’t pace the sideline or interact with the team the same way. Initially, Jackson was worried this would affect his coaching. In fact, sitting back on the sideline above the rest of the bench increased his authority. He learned how to assert himself without ever being overbearing the way he’d been in the past.” ( :88)

“Lose money? Remember, you could have lost a friend. Lost that job? What if you’d lost a limb? Lost your house? You could have lost everything.” ( :88)

“My formula for greatness in a human being is amor f ati: that one wants nothing to be different, not forward, not backward, not in all eternity. Not merely bear what is necessary, still less conceal it . . . but love it. —NIETZSCHE” ( :90)

“Edison calmly but quickly made his way to the fire, through the now hundreds of onlookers and devastated employees, looking for his son. “Go get your mother and all her friends,” he told his son with childlike excitement. “They’ll never see a fire like this again.” What?! Don’t worry, Edison calmed him. “It’s all right. We’ve just got rid of a lot of rubbish.” That’s a pretty amazing reaction. But when you think about it, there really was no other response. What should Edison have done? Wept? Gotten angry? Quit and gone home? What, exactly, would that have accomplished? You know the answer now: nothing.” ( :90)

“Within about three weeks, the factory was partially back up and running. Within a month, its men were working two shifts a day churning out new products the world had never seen. Despite a loss of almost $1 million dollars (more than $23 million in today’s dollars), Edison would marshal enough energy to make nearly $10 million dollars in revenue that year ($200-plus million today). He not only suffered a spectacular disaster, but he recovered and replied to it spectacularly.” ( :91)

“And Johnson, genuinely hated by his opponent and the crowd, still enjoying every minute of it. Smiling, joking, playing the whole fight. Why not? There’s no value in any other reaction. Should he hate them for hating him? Bitterness was their burden and Johnson refused to pick it up.” ( :91)

“As Jack London, the famous novelist, reported from ringside seats: No one understands him, this man who smiles. Well, the story of the fight is the story of a smile. If ever a man won by nothing more fatiguing than a smile, Johnson won today.” ( :91)

“As the Stoics commanded themselves: Cheerfulness in all situations, especially the bad ones. Who knows where Edison and Johnson learned this epithet, but they clearly did.” ( :91)

“Not: I’m okay with this. Not: I think I feel good about this. But: I feel great about it. Because if it happened, then it was meant to happen, and I am glad that it did when it did. I am meant to make the best of it.” ( :92)

“f persistence is attempting to solve some difficult problem with dogged determination and hammering until the break occurs, then plenty of people can be said to be persistent. But perseverance is something larger. It’s the long game. It’s about what happens not just in round one but in round two and every round after—and then the fight after that and the fight after that, until the end.” ( :93)

“There are far more failures in the world due to a collapse of will than there will ever be from objectively conclusive external events.” ( :94)

“As Emerson wrote in 1841, If our young men miscarry in their first enterprises, they lose all heart. If the young merchant fails, men say he is ruined. If the finest genius studies at one of our colleges, and is not installed in an office within one year afterwards in the cities or suburbs of Boston or New York, it seems to his friends and to himself that he is right in being disheartened, and in complaining the rest of his life” ( :94)

“The true threat to determination, then, is not what happens to us, but us ourselves. Why would you be your own worst enemy? Hold on and hold steady.” ( :95)

“A man’s job is to make the world a better place to live in, so far as he is able—always remembering the results will be infinitesimal—and to attend to his own soul. —LEROY PERCY” ( :96)

“Stockdale (then, a commander), aware that he would be the highest-ranking Navy POW the North Vietnamese had ever captured, knew he couldn’t do anything about his fate. But as a commanding officer, he could provide leadership and support and direction to his fellow prisoners (who included future senator John McCain). He could change that situation and not let history repeat itself—this would be his cause, and he would help his men and lead them. Which is exactly what he proceeded to do for more than seven years; two of which were spent wearing leg irons in solitary confinement.” ( :96)

“You’re young, you didn’t cause this, it isn’t your fault. We all got screwed. This only makes it easier to lose our sense of self, to say nothing of our sense of others. To think—if only privately—I don’t care about them, I’ve got to get mine before it’s too late.” ( :97)

“the artist and musician Henry Rollins managed to express this deeply human obligation better than millennia of religious doctrine ever have: People are getting a little desperate. People might not show their best elements to you. You must never lower yourself to being a person you don’t like. There is no better time than now to have a moral and civic backbone. To have a moral and civic true north. This is a tremendous opportunity for you, a young person, to be heroic.” ( :97)

“Pride can be broken. Toughness has its limits. But a desire to help? No harshness, no deprivation, no toil should interfere with our empathy toward others. Compassion is always an option. Camaraderie as well. That’s a power of the will that can never be taken away, only relinquished.” ( :98)

“n late 1569, a French nobleman named Michel de Montaigne was given up as dead after being flung from a galloping horse. As his friends carried his limp and bloodied body home, Montaigne watched life slip away from his physical self, not traumatically but almost flimsily, like some dancing spirit on the “tip of his lips.” Only to have it return at the last possible second. This sublime and unusual experience marked the moment Montaigne changed his life. Within a few years, he would be one of the most famous writers in Europe. After his accident, Montaigne went on to write volumes of popular essays, serve two terms as mayor, travel internationally as a dignitary, and serve as a confidante of the king.” ( :99)

“Every culture has its own way of teaching the same lesson: Memento mori, the Romans would remind themselves. Remember you are mortal.” ( :100)

“It’s a cliché question to ask, What would I change about my life if the doctor told me I had cancer? After our answer, we inevitably comfort ourselves with the same insidious lie: Well, thank God I don’t have cancer.” ( :100)

“As the Haitian proverb puts it: Behind mountains are more mountains.” ( :102)


The Obstacle Becomes the Way


“The man did not. And so Marcus Aurelius called a council of his soldiers and made a rather extraordinary announcement. They would march against Cassius and obtain the “great prize of war and of victory.” But of course, because it was Marcus, this war prize was something wholly different. They would capture Cassius and endeavor not to kill him, but “. . . forgive a man who has wronged one, to remain a friend to one who has transgressed friendship, to continue faithful to one who has broken faith.”” ( :103)

“”I implore you, the senate, to keep my reign unstained by the blood of any senator. May it never happen.” The obstacle becomes the way, becomes the way.” ( :104)

“There is no special school that these individuals attended (aside from, for many, a familiarity with the ancient wisdom of Stoicism). Nothing that they do is out of reach for us. Rather, they have unlocked something that is very much within each and every person. Tested in the crucible of adversity and forged in the furnace of trial, they realized these latent powers—the powers of perception, action, and the will. With this triad, they: First, see clearly. Next, act correctly. Finally, endure and accept the world as it is.” ( :104)

“But don’t worry, you’re prepared for this now, this life of obstacles and adversity. You know how to handle them, how to brush aside obstacles and even benefit from them. You understand the process. You are schooled in the art of managing your perceptions and impressions. Like Rockefeller, you’re cool under pressure, immune to insults and abuse. You see opportunity in the darkest of places. You are able to direct your actions with energy and persistence. Like Demosthenes, you assume responsibility for yourself—teaching yourself, compensating for disadvantages, and pursuing your rightful calling and place in the world. You are iron-spined and possess a great and powerful will. Like Lincoln, you realize that life is a trial. It will not be easy, but you are prepared to give it everything you have regardless, ready to endure, persevere, and inspire others.” ( :105)

“They were nothing special, nothing that we are not just as capable of being. What they did was simple (simple, not easy). But let’s say it once again just to remind ourselves: See things for what they are. Do what we can. Endure and bear what we must. What blocked the path now is a path. What once impeded action advances action. The Obstacle is the Way.” ( :105)

“To be a philosopher is not merely to have subtle thoughts, nor even to found a school . . . it is to solve some of the problems of life, not only theoretically, but practically. —HENRY DAVID THOREAU” ( :106)

“Marcus Aurelius was emperor of the most powerful empire in the history of the world. Cato, the moral example for many philosophers, never wrote down a word but defended the Roman republic with Stoic bravery until his defiant death. Even Epictetus, the lecturer, had no cushy tenure—he was a former slave.” ( :106)

“Frederick the Great was said to ride with the works of the Stoics in his saddlebags because they could, in his words, “sustain you in misfortune.” Montaigne, the politician and essayist, had a line from Epictetus carved into the beam above the study in which he spent most of his time. George Washington was introduced to Stoicism by his neighbors at age seventeen, then he put on a play about Cato to inspire his men in that dark winter at Valley Forge. When Thomas Jefferson died, he had a copy of Seneca on his nightstand. The economist Adam Smith’s theories on the interconnectedness of the world—capitalism—were significantly influenced by the Stoicism he’d studied as a schoolboy under a teacher who’d translated the works of Marcus Aurelius. Eugène Delacroix, the renowned French Romantic artist (known best for his painting Liberty Leading the People) was an ardent Stoic, referring to it as his “consoling religion.” Toussaint Louverture, himself a former slave who challenged an emperor, read and was deeply influenced by the works of Epictetus. The political thinker John Stuart Mill wrote of Marcus Aurelius and Stoicism in his famous treatise On Liberty, calling it “the highest ethical product of the ancient mind.”” ( :106)

“Over the centuries though, this kind of wisdom has been taken from us, co-opted and deliberately obscured by selfish, sheltered academics. They deprived us of philosophy’s true use: as an operating system for the difficulties and hardships of life.” ( :107)

“The Latin translation for the title of Enchiridion—Epictetus’s famous work—means “close at hand,” or as some have said, “in your hands.” That’s what the philosophy was meant for: to be in your hands, to be an extension of you. Not something you read once and put up on a shelf. It was meant, as Marcus once wrote, to make us boxers instead of fencers—to wield our weaponry, we simply need to close our fists. Hopefully, in some small way, this book has translated those lessons and armed you with them. Now you are a philosopher and a person of action. And that is not a contradiction.” ( :107)

“Meditations by Marcus Aure lius (Mode rn Library). There is one translation of Marcus Aurelius to read and that is Gregory Hayes’s amazing edition for the Modern Library. Everything else falls sadly short. His version is completely devoid of any “thou’s” “arts” “shalls.” It’s beautiful and hauting. I’ve recommended this book to literally thousands of people at this point. Buy it. Change your life. Letters of a Stoic by Se ne ca (see also: On the Shortness of Life). Both these translations by Penguin are fantastic. Seneca or Marcus are the best places to start if you’re looking to explore Stoicism. Seneca seems like he would have been a fun guy to know—which is unusual for a Stoic. I suggest starting with On the Shortness of Life (a collection of short essays) and then move to his book of letters (which are really more like essays than true correspondence). Discourses by Epicte tus (Pe nguin). Personally, I prefer the Penguin translations, but I’ve tried a handful of others and found the differences to be relatively negligible. Of the big three, Epictetus is the most preachy and least fun to read. But he will also from time to time express something so clearly and profoundly that it will shake you to your core. The above translations were the ones I used for this book.” ( :114)

“Some other great authors/philosophers to read—particularly their books of maxims or aphorisms, which are in line with a lot of stoic thinking: Heraclitus Plutarch Socrates Cicero Montaigne Arthur Schopenhauer” ( :115)

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