The Obstacle is the Way: The Timeless Art of Turning Adversity to Advantage

by Ryan Holiday

All great victories, be they in politics, business, art, or seduction, involved resolving vexing problems with a potent cocktail of creativity, focus, and daring.

In other words, through our perception of events, we are complicit in the creation—as well as the destruction—of every one of our obstacles. 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. That’s a thought that changes everything, doesn’t it?

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.

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

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.”

Everything is planned down to the letter, then something goes wrong and the first thing we do is trade in our plan for a good ol’ emotional freak-out. Some of us almost crave sounding the alarm, because it’s easier than dealing with whatever is staring us in the face.

So go ahead, feel it. Just don’t lie to yourself by conflating emoting about a problem and dealing with it. Because they are as different as sleeping and waking.

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.

Everything about our animalistic brains tries to compress the space between impression and perception. Think, perceive, act—with milliseconds between them. A deer’s brain tells it to run because things are bad. It runs. Sometimes, right into traffic. We can question that impulse. We can disagree with it. We can override the switch, examine the threat before we act. But this takes strength. It’s a muscle that must be developed.

Take your situation and pretend it is not happening to you. Pretend it is not important, that it doesn’t matter. How much easier would it be for you to know what to do? How much more quickly and dispassionately could you size up the scenario and its options?

The more skilled you become seeing things for what they are, the more perception will work for you rather than against you.

George Clooney spent his first years in Hollywood getting rejected at auditions. He wanted the producers and directors to like him, but they didn’t and it hurt and he blamed the system for not seeing how good he was. This perspective should sound familiar. It’s the dominant viewpoint for the rest of us on job interviews, when we pitch clients, or try to connect with an attractive stranger in a coffee shop. We subconsciously submit to what 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. From Clooney’s new perspective, he was that solution. He wasn’t going to be someone groveling for a shot. He was someone with something special to offer. He was the answer to their prayers, not the other way around. That was what he began projecting in his auditions—not exclusively his acting skills but that he was the man for the job. That he understood what the casting director and producers were looking for in a specific role and that he would deliver it in each and every situation, in preproduction, on camera, and during promotion. The difference between the right and the wrong perspective is everything. How we interpret the events in our lives, our perspective, is ...

So what if you focused on what you can change? That’s where you can make a difference. Behind the Serenity Prayer is a two-thousand-year-old Stoic phrase: “ta eph’hemin, ta ouk eph’hemin.” 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 This is our playing field, so to speak. Everything there is fair game. What is not up to us? Well, you know, everything else. The weather, the economy, circumstances, other people’s emotions or judgments, trends, disasters, et cetera.

It doesn’t matter whether this is the worst time to be alive or the best, whether you’re in a good job market or a bad one, or that the obstacle you face is intimidating or burdensome. What matters is that right now is right now. The implications of our

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. One thing is certain. It’s not simply a matter of saying: Oh, I’ll live in the present. You have to work at it. Catch your mind when it wanders—don’t let it get away from you. Discard distracting thoughts. Leave things well enough alone—no matter how much you feel like doing otherwise.

He knew that to aim low meant to accept mediocre accomplishment. But a high aim could, if things went right, create something extraordinary.

For most of us, such confidence does not come easy. It’s understandable. So many people in our lives have preached the need to be realistic or conservative or worse—to not rock the boat. This is an enormous disadvantage when it comes to trying big things. Because though our doubts (and self-doubts) feel real, they have very little bearing on what is and isn’t possible. Our perceptions determine, to an incredibly large degree, what we are and are not capable of. In many ways, they determine reality itself. When we believe in the obstacle more than in the goal, which will inevitably triumph? For

This is why we shouldn’t listen too closely to what other people say (or to what the voice in our head says, either). We’ll find ourselves erring on the side of accomplishing nothing. Be open. Question. Though of course we don’t control reality, our perceptions do influence it.

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. An entrepreneur is someone with faith in their ability to make something where there was nothing before. To them, the idea that no one has ever done this or that is a good thing. When given an unfair task, some rightly see it as a chance to test what they’re made of—to give it all they’ve got, knowing full well how difficult it will be to win. They see it as an opportunity because it is often in that desperate nothing-to-lose state that we are our most creative. Our best ideas come from there, where obstacles illuminate new options.

that question. Striding into the conference room at headquarters in Malta, General Dwight D. Eisenhower made an announcement: He’d have no more of this quivering timidity from his deflated generals. “The present situation is to be regarded as opportunity for us and not disaster,” he commanded. “There will be only cheerful faces at this conference table.”

Yet we are so bad at looking. We close our eyes to the gift.

having a bad boss. All we see is the hell. All we see is that thing bearing down on us. We flinch. But what if you regarded it as an opportunity instead of a disaster? If you mean it when you say you’re at the end of your rope and would rather quit, you actually have a unique chance to grow and improve yourself. A unique opportunity to experiment with different solutions, to try different tactics, or to take on new projects to add to your skill set. You can study this bad boss and learn from him—while you fill out your résumé and hit up contacts for a better job elsewhere. You can prepare yourself for that job by trying new styles of communication or standing up for yourself, all with a perfect safety net for yourself: quitting and getting out of there. With this new attitude and fearlessness, who knows, you might be able to extract concessions and find that you like the job again. One day, the boss will make a mistake, and then you’ll make your move and outmaneuver them. It will feel so much better than the alternative—whining, bad-mouthing, duplicity, spinelessness.

This is why stories of great success are often preceded by epic failure—because the people in them went back to the drawing board. They weren’t ashamed to fail, but spurred on, piqued by it.

Being outnumbered, coming from behind, being low on funds, these don’t have to be disadvantages. They can be gifts. Assets that make us less likely to commit suicide with a head-to-head attack. These things force us to be creative, to find workarounds, to sublimate the ego and do anything to win besides challenging our enemies where they are strongest. These are the signs that tell us to approach from an oblique angle.

Sometimes in your life you need to have patience—wait 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. 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. We get so consumed with moving forward that we forget that there are other ways to get where we are heading. It doesn’t naturally occur to us that standing still—or in some cases, even going backward—might be the best way to advance. Don’t just do something, stand there! We push and push—to get a raise, a new client, to prevent some exigency from happening. In fact, the best way to get what we want might be to reexamine those desires in the first place. Or it might be to aim for something else entirely, and use the impediment as an opportunity to explore a new direction. In doing so, we might end up creating a new venture that replaces our insufficient income entirely. Or we might discover that in ignoring clients, we attract more—finding that they want to work with someone who does not so badly want to work with them. Or we rethink that disaster we feared (along with everyone else) and come up with a way to profit from it when and if it happens. We wrongly assume that m...

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.

It’s much easier to control our perceptions and emotions than it is to give up our desire to control other people and events. It’s easier to persist in our efforts and actions than to endure the uncomfortable or the painful. It’s easier to think and act than it is to practice wisdom. 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.

Stop making it harder on yourself by thinking about I, I, I. Stop putting that dangerous “I” in front of events. I did this. I was so smart. I had that. I deserve better than this. No wonder you take losses personally, no wonder you feel so alone. You’ve inflated your own role and importance.

Help your fellow humans thrive and survive, contribute your little bit to the universe before it swallows you up, and be happy with that. Lend a hand to others. Be strong for them, and it will make you stronger.

As the Haitian proverb puts it: Behind mountains are more mountains. Elysium is a myth. One does not overcome an obstacle to enter the land of no obstacles. On the contrary, the more you accomplish, the more things will stand in your way. There are always more obstacles, bigger challenges. You’re always fighting uphill.

Passing one obstacle simply says you’re worthy of more. The world seems to keep throwing them at you once it knows you can take it. Which is good, because we get better with every attempt. Never rattled. Never frantic. Always hustling and acting with creativity. Never anything but deliberate. Never attempting to do the impossible—but everything up to that line. Simply flipping the obstacles that life throws at you by improving in spite of them, because of them. And therefore no longer afraid. But excited, cheerful, and eagerly anticipating the next round.

you assume responsibility for yourself—teaching yourself, compensating for disadvantages, and pursuing your rightful calling and place in the world.