Summary, Quotes, and Lessons: The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph by Ryan Holiday


“The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph” is a book written by Ryan Holiday that explores the concept of stoicism and how it can be applied to overcome obstacles in life. Here is a summary of the key points from the book:

  1. Obstacles are opportunities: According to stoicism, obstacles are not something to be feared, but rather something to be embraced. Obstacles provide us with an opportunity to grow and become stronger.
  2. Perception is everything: How we perceive a situation determines how we respond to it. By changing our perception of an obstacle, we can change our response to it.
  3. Action is the solution: Instead of getting stuck in negative thoughts or worrying about what might happen, take action to address the obstacle. Action is the solution to most problems.
  4. Persistence pays off: Overcoming obstacles often requires persistence and determination. By persisting through difficulties, we can build resilience and become stronger.
  5. Practice self-control: Self-control is key to mastering our emotions and thoughts. By practicing self-control, we can remain calm and clear-headed in the face of adversity.
  6. Embrace the present moment: Rather than dwelling on the past or worrying about the future, focus on the present moment. The present is where we have the most control and where we can take action to overcome obstacles.
  7. Find meaning in adversity: Adversity can be a source of meaning and purpose in our lives. By embracing the challenges we face, we can find a deeper sense of purpose and meaning.

Overall, “The Obstacle Is the Way” encourages readers to adopt a stoic mindset and use obstacles as opportunities for growth and self-improvement. By changing our perception of obstacles, taking action, and practicing self-control, we can overcome challenges and achieve success.


“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.”

“The impediment to action advances action. What stands in the way becomes the way.”

“Making certain that what impedes us can empower us.”

“It’s our birthright. Whatever we face, we have a choice: Will we be blocked by obstacles, or will we advance through and over them?”

“What blocks us is clear. Systemic: decaying institutions, rising.”

“John D. Rockefeller had it—for him it was cool headedness and self-discipline. Demosthenes, the great Athenian orator, had it—for him it was a relentless drive to improve himself through action and practice. Abraham Lincoln had it—for him it was humility, endurance, and compassionate will.”

“Bad companies are destroyed by crisis. Good companies survive them. Great companies are improved by them.”

“The obstacle in the path becomes the path. Never forget, within every obstacle is an opportunity to improve our condition.”

“The Things which hurt,” Benjamin Franklin wrote, “instruct.”

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

“Overcoming obstacles is a discipline of three critical steps. It begins with how we look at our specific problems, our attitude or approach; then the energy and creativity with which we actively break them down and turn them into opportunities; finally, the cultivation and maintenance of an inner will that allows us to handle defeat and difficulty.”

“Perception, Action, and the Will.”

“WHAT IS PERCEPTION? It’s how we see and understand what occurs around us—and what we decide those events will mean.”

“To prevent becoming overwhelmed by the world around us, we must, as the ancients practiced, learn how to limit our passions and their control over our lives.”

“As he once put it: He was inclined to see the opportunity in every disaster. To that we could add: He had the strength to resist temptation or excitement, no matter how seductive, no matter the situation.”

Warren Buffet’s famous adage to “be fearful when others are greedy and greedy when others are fearful.”

“Oh, how blessed young men are who have to struggle for a foundation and beginning in life,” he once said.

“Where one person sees a crisis, another can see opportunity.”

“Desperation, despair, fear, powerlessness—these reactions are functions of our perceptions.”

“Outward appearances are deceptive. What’s within them, beneath them, is what matters.”

“Discipline in perception lets you clearly see the advantage and the proper course of action in every situation— without the pestilence of panic or fear.”

Choose not to be harmed—and you won’t feel harmed. Don’t feel harmed—and you haven’t been.


“Instead of breaking down—as many would have done in such a bleak situation—Carter declined to surrender the freedoms that were innately his: his attitude, his beliefs, his choices.”

“Our perceptions are the thing that we’re in complete control of.”

“They can throw us in jail, label us, deprive us of our possessions, but they’ll never control our thoughts, our beliefs, our reactions.”

“To one person a situation may be negative. To another, that same situation may be positive.”

“Just because your mind tells you that something is awful or evil or unplanned or otherwise negative doesn’t mean you have to agree.”

What such a man needs is not courage but nerve control, cool headedness. This he can get only by practice. —THEODORE ROOSEVELT

“When we aim high, pressure and stress obligingly come along for the ride.”

We must possess, as Voltaire once explained about the secret to the great military success of the first Duke of Marlborough, that “tranquil courage in the midst of tumult and serenity of soul in danger, which the English call a cool head.”

Would you have a great empire? Rule over yourself. —PUBLIUS SYRUS

“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. They just react—not to what they need to react to, but to the survival hormones that are coursing through their veins.”

“Panic is suicide.”

“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.”

“Life is really no different. Obstacles make us emotional, but the only way we’ll survive or overcome them is by keeping those emotions in check—if we can keep steady no matter what happens, no matter how much external events may fluctuate.”

As Gavin de Becker writes in The Gift of Fear, “When you worry, ask yourself, ‘What am I choosing to not see right now?’ What important things are you missing because you chose worry over introspection, alertness or wisdom?”

“We defeat emotions with logic, or at least that’s the idea. Logic is questions and statements.”

Don’t let the force of an impression when it first hit you knock you off your feet; just say to it: Hold on a moment; let me see who you are and what you represent. Let me put you to the test. —EPICTETUS

“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.”

“To paraphrase Nietzsche, sometimes being superficial—taking things only at first glance—is the most profound approach.”

“Think, perceive, act—with milliseconds between them.”

“Epictetus 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.”

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.


“Remember: We choose how we’ll look at things. We retain the ability to inject perspective into a situation. We can’t change the obstacles themselves— that part of the equation is set—but the power of perspective can change how the obstacles appear. How we approach, view, and contextualize an obstacle, and what we tell ourselves it means, determines how daunting and trying it will be to overcome.”

“Where the head goes, the body follows. Perception precedes action. Right action follows the right perspective.”

In life our first job is this, to divide and distinguish things into two categories: externals I cannot control, but the choices I make with regard to them I do control. Where will I find good and bad? In me, in my choices. —EPICTETUS

“God, grant me the serenity to accept the things I cannot change The courage to change the things I can, And the wisdom to know the difference”

“When it comes to perception, this is the crucial distinction to make: the difference between the things that are in our power and the things that aren’t.”

“Focusing exclusively on what is in our power magnifies and enhances our power.”

The trick to forgetting the big picture is to look at everything close up. —CHUCK PALAHNIUK

Emerson put it best: “We cannot spend the day in explanation.”

“You’ll find the method that works best for you, but there are many things that can pull you into the present moment: Strenuous exercise. Unplugging. A walk in the park. Meditation. Getting a dog—they’re a constant reminder of how pleasant the present is.”

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

“He knew that to aim low meant to accept mediocre accomplishment.”

“Though of course we don’t control reality, our perceptions do influence it.”

A good person dyes events with his own color . . . and turns whatever happens to his own benefit. —SENECA

As Laura Ingalls Wilder put it: “There is good in everything, if only we look for it.”

“It’s our preconceptions that are the problem. They tell us that things should or need to be a certain way, so when they’re not, we naturally assume that we are at a disadvantage or that we’d be wasting our time to pursue an alternate course.”

“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.”

“That which doesn’t kill me makes me stronger” is not a cliché but fact.

Then imitate the action of the tiger; stiffen the sinews, summon up the blood. —SHAKESPEARE

“A clearer head makes for steadier hands.”

“Our movements and decisions define us: We must be sure to act with deliberation, boldness, and persistence.”

Some academic once asked Demosthenes what the three most important traits of speechmaking were. His reply says it all: “Action, Action, Action!”

“We don’t think, we don’t complain, we don’t argue. We act. We have real strength—more strength than we know.”

“People turn shit into sugar all the time—shit that’s a lot worse than whatever we’re dealing with. I’m talking physical disabilities, racial discrimination, battles against overwhelmingly superior armies. But those people didn’t quit. They didn’t feel sorry for themselves. They didn’t delude themselves with fantasies about easy solutions. They focused on the one thing that mattered: applying themselves with gusto and creativity.”

We must all either wear out or rust out, every one of us. My choice is to wear out. —THEODORE ROOSEVELT

“Tell yourself: The time for that has passed. The wind is rising. The bell’s been rung. Get started, get moving.”

“So the first step is: Take the bat off your shoulder and give it a swing. You’ve got to start, to go anywhere.”

“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.”

“Be deliberate, of course, but you always need to be moving forward.”

“Just as Earhart did, all the greats you admire started by saying, Yes, let’s go. And they usually did it in less desirable circumstances than we’ll ever suffer.”

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

“If we’re to overcome our obstacles, this is the message to broadcast— internally and externally. We will not be stopped by failure, we will not be rushed or distracted by external noise. We will chisel and peg away at the obstacle until it is gone. Resistance is futile.”

“At Vicksburg, Grant learned two things. First, persistence and pertinacity were incredible assets and probably his main assets as a leader. Second, as often is the result from such dedication, in exhausting all the other traditional options, he’d been forced to try something new.”

The Alfred Lord Tennyson poem about that other Ulysses, “to strive, to seek, to find.”

As Margaret Thatcher famously did: “You turn if you want to. The lady’s not for turning.”

“Remember and remind yourself of a phrase favored by Epictetus: “persist and resist.” Persist in your efforts. Resist giving in to distraction, discouragement, or disorder.”

“When setbacks come, we respond by working twice as hard.”

What is defeat? Nothing but education; nothing but the first steps to something better. —WENDELL PHILLIPS

“There’s nothing shameful about being wrong, about changing course. Each time it happens we have new options. Problems become opportunities.”

” Our capacity to try, try, try is inextricably linked with our ability and tolerance to fail, fail, fail.”

“Failure shows us the way—by showing us what isn’t the way.”

Under the comb the tangle and the straight path are the same. —HERACLITUS

“Excellence is a matter of steps.”

“When it comes to our actions, disorder and distraction are death.”

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

Whatever is rightly done, however humble, is noble. (Quidvis recte factum quamvis humile praeclarum.) —SIR HENRY ROYCE

As Andrew Carnegie famously put it. There’s nothing shameful about sweeping. It’s just another opportunity to excel —and to learn.

“Wherever we are, whatever we’re doing and wherever we are going, we owe it to ourselves, to our art, to the world to do it well. That’s our primary duty. And our obligation. When action is our priority, vanity falls away.”

The cucumber is bitter? Then throw it out. There are brambles in the path? Then go around. That’s all you need to know. —MARCUS AURELIUS

“We spend a lot of time thinking about how things are supposed to be, or what the rules say we should do. Trying to get it all perfect. We tell ourselves that we’ll get started once the conditions are right, or once we’re sure we can trust this or that. When, really, it’d be better to focus on making due with what we’ve got. On focusing on results instead of pretty methods.”

“Pragmatism is not so much realism as flexibility. There are a lot of ways to get from point A to point B. It doesn’t have to be a straight line. It’s just got to get you where you need to go. But so many of us spend so much time looking for the perfect solution that we pass up what’s right in front of us.”

As Deng Xiaoping once said, “I don’t care if the cat is black or white, so long as it catches mice.”

“Think progress, not perfection.”

Whoever cannot seek the unforeseen sees nothing, for the known way is an impasse. —HERACLITUS

Never attack where it is obvious, Washington told his men. Don’t attack as the enemy would expect, he explained, instead, “Where little danger is apprehended, the more the enemy will be unprepared and consequently there is the fairest prospect of success.”

“As Hart writes in his masterwork Strategy: [T]he Great Captain will take even the most hazardous indirect approach —if necessary over mountains, deserts or swamps, with only a fraction of the forces, even cutting himself loose from his communications. Facing, in fact, every unfavorable condition rather than accept the risk of stalemate invited by direct approach.”

As someone once put it after fighting Jigoro Kano, the legendary five-foot[1]tall founder of judo, “Trying to fight with Kano was like trying to fight with an empty jacket!”

“He would rarely tell the reader “do this” or “think that.” Instead he would show new ways of looking at or understanding the world.”

“Remember, sometimes the longest way around is the shortest way home.”

Wise men are able to make a fitting use even of their enmities. —PLUTARCH

“When we want things too badly we can be our own worst enemy. In our eagerness, we strip the very screw we want to turn and make it impossible to ever get what we want. We spin our tires in the snow or mud and dig a deeper rut—one that we’ll never get out of.”

The great strategist Saul Alinsky believed that if you “push a negative hard enough and deep enough it 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.”

When jarred, unavoidably, by circumstance revert at once to yourself and don’t lose the rhythm more than you can help. You’ll have a better grasp of harmony if you keep going back to it. —MARCUS AURELIUS

His style is best described in the epithet he created for himself: “physically loose and mentally tight.”

“External factors influence the path, but not the direction: forward.”

The best men are not those who have waited for chances but who have taken them; besieged chance, conquered the chance, and made chance the servitor. —E. H. CHAPIN

Ignore the politics and focus on the brilliant strategic advice that Obama’s adviser Rahm Emanuel, once gave him. “You never want a serious crisis to go to waste. Things that we had postponed for too long, that were long-term, are now immediate and must be dealt with. [A] crisis provides the opportunity for us to do things that you could not do before.”

“Ordinary people shy away from negative situations, just as they do with failure.”

“You forget: Life speeds on the bold and favors the brave.”

“Napoleon described war in simple terms: Two armies are two bodies that clash and attempt to frighten each other. At impact, there is a moment of panic and it is that moment that the superior commander turns to his advantage.”

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

“Problems, as Duke Ellington once said, are a chance for us to do our best.”

“As crafty and ambitious and smart as he was, Lincoln’s real strength was his will: the way he was able to resign himself to an onerous task without giving in to hopelessness, the way he could contain both humor and deadly seriousness, the way he could use his own private turmoil to teach and help others, the way he was able to rise above the din and see politics philosophically. “This too shall pass” was Lincoln’s favorite saying, one he once said was applicable in any and every situation one could encounter.”

“Leadership requires determination and energy.”

”If Perception and Action were the disciplines of the mind and the body, then Will is the discipline of the heart and the soul.”

“Even in his own time, Lincoln’s contemporaries marveled at the calmness, the gravity, and compassion of the man. Today, those qualities seem almost godlike —almost superhuman.”

Schooled in suffering, to quote Virgil, Lincoln learned “to comfort those who suffer too.”

“But he also embodied the Stoic maxim: sustine et abstine. Bear and forbear.”

“Certain things in life will cut you open like a knife.”

If thy faint in the day of adversity, thy strength is small. —PROVERBS 24:10

“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.”

“Many saw themselves as mental athletes—after all, the brain is a muscle like any other active tissue. It can be built up and toned through the right exercises. Over time, their muscle memory grew to the point that they could intuitively respond to every situation. Especially obstacles.”

“No one is born a gladiator.”

Offer a guarantee and disaster threatens. —ANCIENT INSCRIPTION AT THE ORACLE OF DELPHI

“A premortem is different. In it, we look to envision what could go wrong, what will go wrong, in advance, before we start. Far too many ambitious undertakings fail for preventable reasons.”

“Your plan and the way things turn out rarely resemble each other.”

“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.”

“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.”

“Common wisdom provides us with the maxims: 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.”

“Chimeras are like bandages—they hurt only when torn away.”

The Fates guide the person who accepts them and hinder the person who resists them. —CLEANTHES

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

My formula for greatness in a human being is amor fati: 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

“As the Stoics commanded themselves: Cheerfulness in all situations, especially the bad ones.”

“Gentleman, I am hardening on this enterprise. I repeat, I am now hardening towards this enterprise.” —WINSTON CHURCHILL

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

“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.”

“Embrace this power, this sense of being part of a larger whole. It is an exhilarating thought. Let it envelop you. We’re all just humans, doing the best we can. We’re all just trying to survive, and in the process, inch the world forward a little bit.”

When a man knows he is to be hanged in a fortnight, it concentrates his mind wonderfully. —DR. JOHNSON

As Shakespeare wrote in The Tempest not many years later, as he himself was growing older, “Every third thought shall be my grave.”

“Part of the reason we have so much trouble with acceptance is because our relationship with our own existence is totally messed up.”

“The paths of glory, Thomas Gray wrote, lead but to the grave.”

“Reminding ourselves each day that we will die helps us treat our time as a gift.”

Live on in your blessings, your destiny’s been won. But ours calls us on from one ordeal to the next. —VIRGIL

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

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.”

Marcus once reminded himself that “when the fire is strong, it soon appropriates to itself the matter which is heaped on it, and consumes it, and rises higher by means of this very material.”

“With this triad, they: First, see clearly. Next, act correctly. Finally, endure and accept the world as it is.”

The philosopher and writer Nassim Nicholas Taleb defined a Stoic as someone who “transforms fear into prudence, pain into transformation, mistakes into initiation and desire into undertaking.”

“We gather strength as we go.”

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

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