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

by Ryan Holiday

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? You could write it off, greet it calmly.

Perspective is everything.

The Greeks understood that we often choose the ominous explanation over the simple one, to our detriment. That we are scared of obstacles because our perspective is wrong—that a simple shift in perspective can change our reaction entirely. The task, as Pericles showed, is not to ignore fear but to explain it away. Take what you’re afraid of—when fear strikes you—and break it apart.

And with the wrong perspective, we become consumed and overwhelmed with something actually quite small. So why subject ourselves to that?

Richard Branson likes to say, is that “business opportunities are like buses; there’s always another coming around.”

How we interpret the events in our lives, our perspective, is the framework for our forthcoming response—whether there will even be one or whether we’ll just lie there and take it.

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

This is how they focus their efforts. It’s a lot easier to fight addiction when you aren’t also fighting the fact that you were born, that your parents were monsters, or that you lost everything. That stuff is done. Delivered. Zero in one hundred chances that you can change it.

Focusing exclusively on what is in our power magnifies and enhances our power. But every ounce of energy directed at things we can’t actually influence is wasted—self-indulgent and self-destructive. So much power—ours, and other people’s—is frittered away in this manner.

Those who survive it, survive because they took things day by day—that’s the real secret.

Focus on the moment, not the monsters that may or may not be up ahead.

For all species other than us humans, things just are what they are. Our problem is that we’re always trying to figure out what things mean—why things are the way they are. As though the why matters. Emerson put it best: “We cannot spend the day in explanation.” Don’t waste time on false constructs.

What matters is that right now is right now.

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.

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?

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.

Of course, none of these things affect the objective reality of that deadline. Not in the way that pushing forward can. Jobs refused to tolerate people who didn’t believe in their own abilities to succeed. Even if his demands were unfair, uncomfortable, or ambitious.

It’s this all-too-common impulse to complain, defer, and then give up that holds us back.

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.”

you’re looking not at the obstacle but at the opportunity within 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. When really, it’s all fair game, and every situation is an opportunity for us to act.

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.

How about that business decision that turned out to be a mistake? Well, you had a hypothesis and it turned out to be wrong. Why should that upset you? It wouldn’t piss off a scientist, it would help him.

Of all the strategies we’ve talked about, this is the one you can always use. Everything can be flipped, seen with this kind of gaze: a piercing look that ignores the package and sees only the gift. Or we can fight it the entire way. The result is the same. The obstacle still exists. One just hurts less. The benefit is still there below the surface. What kind of idiot decides not to take it?

Seeing through the negative, past its underside, and into its corollary: the positive.

Once you see the world as it is, for what it is, you must act. The proper perception—objective, rational, ambitious, clean—isolates the obstacle and exposes it for what it is.

But boldness is acting anyway, even though you understand the negative and the reality of your obstacle. Decide to tackle what stands in your way—not because you’re a gambler defying the odds but because you’ve

calculated them and boldly embraced the risk.

directed action. Everything must be done in the service of the whole. Step by step, action by action, we’ll dismantle the obstacles in front of us. With persistence and flexibility, we’ll act in the best interest of our goals. Action requires courage, not brashness—creative application and not brute force.

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.

Every moment, every conversation, every transaction, was an opportunity for him to improve his art.

He would be successful precisely because of what he’d been through and how he’d reacted to it.

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? There’s an explosion, metaphoric or otherwise. Are you the guy running toward it? Or running away from it? Or worse, are you paralyzed and do nothing?

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.

We forget: In life, it doesn’t matter what happens to you or where you came from. It matters what you do with what happens and what you’ve been given. And the only way you’ll do something spectacular is by using it all to your advantage.

No one is saying you can’t take a minute to think, Dammit, this sucks. By all means, vent. Exhale. Take stock. Just don’t take too long. Because you have to get back to work. Because each obstacle we overcome makes us stronger for the next one.

Therefore, we can always (and only) greet our obstacles with energy with persistence with a coherent and deliberate process with iteration and resilience with pragmatism with strategic vision with craftiness and savvy and an eye for opportunity and pivotal moments

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

Because that’s what people who defy the odds do. That’s how people who become great at things—whether it’s flying or blowing through gender stereotypes—do. They start. Anywhere. Anyhow.

What mattered was that she took the opening and then pressed ahead. That was the reason for her success.

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

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.

“Always think with your stick forward.” That is: You can’t ever let up your flying speed—if you do, you crash. Be deliberate, of course, but you always need to be moving forward.

Stay moving, always.

Just because the conditions aren’t exactly to your liking, or you don’t feel ready yet, doesn’t mean you get a pass. If you want momentum, you’ll have to create it yourself, right now, by getting up and getting started.

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.

genius often really is just persistence in disguise.

Epictetus: “persist and resist.” Persist in your efforts. Resist giving in to distraction, discouragement, or disorder.

Stop looking for an epiphany, and start looking for weak points. Stop looking for angels, and start looking for angles. There are options. Settle in for the long haul and then try each and every possibility, and you’ll get there.