The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph

by Ryan Holiday

It turns out that the wisdom of that short passage from Marcus Aurelius can be found in others as well, men and women who followed it like he did. In fact, it is a remarkable constant down through the ages. One can trace the thread from those days in the decline and fall of the Roman Empire to the creative outpouring of the Renaissance to the breakthroughs of the Enlightenment. It’s seen starkly in the pioneer spirit of the American West, the perseverance of the Union cause during the Civil War, and in the bustle of the Industrial Revolution. It appeared again in the bravery of the leaders of the civil rights movement and stood tall in the prison camps of Vietnam. And today it surges in the DNA of the entrepreneurs of Silicon Valley.

This philosophic approach is the driving force of self-made men and the succor to those in positions with great responsibility or great trouble. On the battlefield or in the boardroom, across oceans and many centuries, members of every group, gender, class, cause, and business have had to confront obstacles and struggle to overcome them—learning to turn those obstacles upside down.

We are the rightful heirs to this tradition. 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?

We might not be emperors, but the world is still constantly testing us. It asks: Are you worthy? Can you get past the things that inevitably fall in your way? Will you stand up and show us what you’re made of?

Plenty of people have answered this question in the affirmative. And a rarer breed still has shown that they not only have what it takes, but they thrive and rally at every such challenge. That the challenge makes them better than if they’d never faced the adversity at all. Now ...

What blocks us is clear. Systemic: decaying institutions, rising unemployment, skyrocketing costs of education, and technological disruption. Individual: too short, too old, too scared, too poor, too stressed, no access, no backers, no confidence. How skilled we are at cataloging what holds us back! Every obstacle is unique to each of us. But the responses they elicit are the same: Fear. Frustration. Confusion. Helplessness. Depression. Anger. You know what you want to do but it feels like some invisible enemy has you boxed in, holding you down with pillows. You try to get somewhere, but something invariably blocks the path, following and thwarting each move you make. You have just enough freedom to feel like you can move; just enough to feel like it’s your fault when you can’t seem to follow through or build momentum.

We watch in awe as some seem to turn those very obstacles, which stymie us, into launching pads for themselves. How do they do that? What’s the secret? Even more perplexing, earlier generations faced worse problems with fewer safety nets and fewer tools. They dealt with the same obstacles we have today plus the ones they worked so hard to try to eliminate for their children and others. And yet . . . we’re still stuck. What do these figures have that we lack? What are we missing? It’s simple: a method and a framework for understanding, appreciating, and acting upon the obstacles life throws at us.

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.

Some of these men and women faced unimaginable horrors, from imprisonment to debilitating illnesses, in addition to day-to-day frustrations that were no different from ours. They dealt with the same rivalries, political headwinds, drama, resistance, conservatism, breakups, stresses, and economic calamities. Or worse. Subjected to those pressures, these individuals were transformed. They were transformed along the lines that Andy Grove, former 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.”

Great individuals, like great companies, find a way to transform weakness into strength. It’s a rather amazing and even touching feat. They took what should have held them back—what in fact might be holding you back right this very second—and used it to move forward.

They had the ability to see obstacles for what they were, the ingenuity to tackle them, and the will to endure a world mostly beyond their comprehension and control.

Most of the time we don’t find ourselves in horrible situations we must simply endure. Rather, we face some minor disadvantage or get stuck with some less-than-favorable conditions. Or we’re trying to do something really hard and find ourselves outmatched, overstretched, or out of ideas. Well, the same logic applies. Turn it around. Find some benefit. Use it as fuel.

Ancient philosophy never cared much for authorship or originality—all writers did their best to translate and explain the wisdom of the greats as it has been passed down in books, diaries, songs, poems, and stories. All of these, refined in the crucible of human experience over thousands of years.

So this will be a book of ruthless pragmatism and stories from history that illustrate the arts of relentless persistence and indefatigable ingenuity. It teaches you how to get unstuck, unfucked, and unleashed. How to turn the many negative situations we encounter in our lives into positive ones—or at least to snatch whatever benefit we can from them. To steal good fortune from misfortune.

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

These are obstacles. I get it. No one is denying that. 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? Well, far too many gave up. But a few didn’t. They took “twice as good” as a challenge. They practiced harder. Looked for shortcuts and weak spots. Discerned allies among strange faces. Got kicked around a bit. Everything was an obstacle they had to flip.

Within those obstacles was an opportunity. They seized it. They did something special because of it. We can learn from them.

All great victories, be they in politics, business, art, or seduction, involved resolving vexing problems with a potent cocktail of creativity, focus, and daring. When you have a goal, obstacles are actually teaching you how to get where you want to go—carving you a path. “The Things which hurt,” Benjamin Franklin wrote, “instruct.”

Many of our problems come from having too much: rapid technological disruption, junk food, traditions that tell us the way we’re supposed to live our lives. We’re soft, entitled, and scared of conflict. Great times are great softeners. Abundance can be its own obstacle, as many people can attest. Our generation needs an approach for overcoming obstacles and thriving amid chaos more than ever. One that will help turn our problems on their heads, using them as canvases on which to paint master works. This flexible approach is fit for an entrepreneur or an artist, a conqueror or a coach, whether you’re a struggling writer or a sage or a hardworking soccer mom.

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. It’s three interdependent, interconnected, and fluidly contingent disciplines: Perception, Action, and the Will.

From the stories of the practitioners we’ll learn how to handle common obstacles—whether we’re locked out or hemmed in, the kind of obstacles that have impeded people for all time—and how to apply their general approach to our lives. Because obstacles are not only to be expected but embraced.

🙌🏾

WHAT IS PERCEPTION? It’s how we see and understand what occurs around us—and what we decide those events will mean. Our perceptions can be a source of strength or of great weakness. If we are emotional, subjective and shortsighted, we only add to our troubles. 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. It takes skill and discipline to bat away the pests of bad perceptions, to separate reliable signals from deceptive ones, to filter out prejudice, expectation, and fear. But it’s worth it, for what’s left is truth. 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.

But even as a young man, Rockefeller had sangfroid: unflappable coolness under pressure. He could keep his head while he was losing his shirt. Better yet, he kept his head while everyone else lost theirs. And so instead of bemoaning this economic upheaval, Rockefeller eagerly observed the momentous events. Almost perversely, he chose to look at it all as an opportunity to learn, a baptism in the market. He quietly saved his money and watched what others did wrong. He saw the weaknesses in the economy that many took for granted and how this left them all unprepared for change or shocks.

He internalized an important lesson that would stay with him forever: The market was inherently unpredictable and often vicious—only the rational and disciplined mind could hope to profit from it. Speculation led to disaster, he realized, and he needed to always ignore the “mad crowd” and its inclinations. Rockefeller immediately put those insights to use.

Within twenty years of that first crisis, Rockefeller would alone control 90 percent of the oil market. His greedy competitors had perished. His nervous colleagues had sold their shares and left the business. His weak-hearted doubters had missed out. For the rest of his life, the greater the chaos, the calmer Rockefeller would become, particularly when others around him were either panicked or mad with greed. He would make much of his fortune during these market fluctuations—because he could see while others could not. This insight lives on today in Warren Buffet’s famous adage to “be fearful when others are greedy and greedy when others are fearful.” Rockefeller, like all great investors, could resist impulse in favor of cold, hard common sense.

One critic, in awe of Rockefeller’s empire, described the Standard Oil trust as a “mythical protean creature” capable of metamorphosing with every attempt by the competitors or the government to dismantle it. They meant it as a criticism, but it was actually a function of Rockefeller’s personality: resilient, adaptable, calm, brilliant. He could not be rattled—not by economic crisis, not by a glittery mirage of false opportunities, not by aggressive, bullying enemies, not even by federal prosecutors (for whom he was a notoriously difficult witness to cross-examine, never rising to take the bait or defend himself or get upset).

“Oh, how blessed young men are who have to struggle for a foundation and beginning in life,” he once said. “I shall never cease to be grateful for the three and half years of apprenticeship and the difficulties to be overcome, all along the way.” Of course, many people experienced the same perilous times as Rockefeller—they all attended the same school of bad times. But few reacted as he did. Not many had trained themselves to see opportunity inside this obstacle, that what befell them was not unsalvageable misfortune but the gift of education—a chance to learn from a rare moment in economic history.

And you will discover, time and time again, that what matters most is not what these obstacles are but how we see them, how we react to them, and whether we keep our composure. You will learn that this reaction determines how successful we will be in overcoming—or possibly thriving because of—them.

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. And it is precisely at this divergence—between how Rockefeller perceived his environment and how the rest of the world typically does—that his nearly incomprehensible success was born. His careful, cautious self-confidence was an incredible form of power.

Outward appearances are deceptive. What’s within them, beneath them, is what matters. We can learn to perceive things differently, to cut through the illusions that others believe or fear. We can stop seeing the “problems” in front of us as problems. We can learn to focus on what things really are.

Our brains evolved for an environment very different from the one we currently inhabit. As a result, we carry all kinds of biological baggage. Humans are still primed to detect threats and dangers that no longer exist—think of the cold sweat when you’re stressed about money, or the fight-or-flight response that kicks in when your boss yells at you. Our safety is not truly at risk here—there is little danger that we will starve or that violence will break out—though it certainly feels that way sometimes. We have a choice about how we respond to this situation (or any situation, for that matter). We can be blindly led by these primal feelings or we can understand them and learn to filter them. 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.

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.

There are a few things to keep in mind when faced with a seemingly insurmountable obstacle. We must try: To be objective To control emotions and keep an even keel To choose to see the good in a situation To steady our nerves To ignore what disturbs or limits others To place things in perspective To revert to the present moment To focus on what can be controlled This is how you see the opportunity within the obstacle. It does not happen on its own. It is a process—one that results from self-discipline and logic.

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

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. Whether they threw him in prison or threw him in solitary confinement for weeks on end, Carter maintained that he still had choices, choices that could not be taken from him even though his physical freedom had been. Was he angry about what happened? 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. All of this had a purpose: Every second of his energy was to be spent on his legal case. Every waking minute was 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.

We decide what we will make of each and every situation. We decide whether we’ll break or whether we’ll resist. We decide whether we’ll assent or reject. No one can force us to give up or to believe something that is untrue (such as, that a situation is absolutely hopeless or impossible to improve). Our perceptions are the thing that we’re in complete control of.

Laura Ingalls Wilder, author of the classic series Little House, lived that idea, facing some of the toughest and unwelcoming elements on the planet: harsh and unyielding soil, Indian territory, Kansas prairies, and the humid backwoods of Florida. Not afraid, not jaded—because she saw it all as an adventure. Everywhere was a chance to do something new, to persevere with cheery pioneer spirit whatever fate befell her and her husband. That isn’t to say she saw the world through delusional rose-colored glasses. Instead, she simply chose to see each situation for what it could be—accompanied by hard work and a little upbeat spirit. Others make the opposite choice.

There is no good or bad without us, there is only perception. There is the event itself and the story we tell ourselves about what it means.

Just because your mind tells you that something is awful or evil or unplanned or otherwise negative doesn’t mean you have to agree. Just because other people say that something is hopeless or crazy or broken to pieces doesn’t mean it is. We decide what story to tell ourselves. Or whether we will tell one at all. Welcome to the power of perception. Applicable in each and every situation, impossible to obstruct. It can only be relinquished. And that is your decision.

Defiance and acceptance come together well in the following principle: There is always a countermove, always an escape or a way through, so there is no reason to get worked up. No one said it would be easy and, of course, the stakes are high, but the path is there for those ready to take it.

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. The Greeks had a word for this: apatheia.

If you need to take a moment, by all means, go ahead. Real strength lies in the control or, as Nassim Taleb put it, the domestication of one’s emotions, not in pretending they don’t exist.

Subconsciously, we should be constantly asking ourselves this question: Do I need to freak out about this? And the answer—like it is for astronauts, for soldiers, for doctors, and for so many other professionals—must be: No, because I practiced for this situation and I can control myself. Or, No, because I caught myself and I’m able to realize that that doesn’t add anything constructive.

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

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. 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.

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

The way we look out at the world changes how we see these things. Is our perspective truly giving us perspective or is it what’s actually causing the problem? That’s the question. What we can do is limit and expand our perspective to whatever will keep us calmest and most ready for the task at hand. Think of it as selective editing—not to deceive others, but to properly orient ourselves. And it works. Small tweaks can change what once felt like impossible tasks. Suddenly, where we felt weak, we realize we are strong. With perspective, we discover leverage we didn’t know we had.

Perspective has two definitions. Context: a sense of the larger picture of the world, not just what is immediately in front of us Framing: an individual’s unique way of looking at the world, a way that interprets its events

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