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

by Ryan Holiday

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...

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

he got really good at asking himself and others, in various forms, one question over and over again: Is there a chance? Do I have a shot? Is there something I can do?

The things that Tommy John could change—when he had a chance—got a full 100 percent of the effort he could muster. He used to tell coaches that he would die on the field before he quit. He understood that as a professional athlete his job was to parse the difference between the unlikely and the impossible. Seeing that minuscule distinction was what made him who he was. To harness the same power, recovering addicts learn the Serenity Prayer.

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.

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

The point is that most people start from disadvantage (often with no idea they are doing so) and do just fine. It’s not unfair, it’s universal. Those who survive it, survive because they took things day by day—that’s the real secret.

You can take the trouble you’re dealing with and use it as an opportunity to focus on the present moment. To ignore the totality of your situation and learn to be content with what happens, as it happens. To have no “way” that the future needs to be to confirm your predictions, because you didn’t make any. To let each new moment be a refresh wiping clear what came before and what others were hoping would come next.

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.

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?

Now, how do you and I usually deal with an impossible deadline handed down from someone above us? We complain. We get angry. We question. How could they? What’s the point? Who do they think I am? We look for a way out and feel sorry for ourselves.

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.

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

Yet we are so bad at looking. We close our eyes to the gift. Imagine if you’d been in Eisenhower’s shoes, with an army racing toward you, and you could see only impending defeat. How much longer would the war have gone on? How many more lives lost?

Let’s take a circumstance we’ve all been in: 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.

The struggle against an obstacle inevitably propels the fighter to a new level of functioning. The extent of the struggle determines the extent of the growth. The obstacle is an advantage, not adversity. The enemy is any perception that prevents us from seeing this. 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? Now the things that other people avoid, or flinch away from, we’re thankful for. When people are: —rude or disrespectful: They underestimate us. A huge advantage. —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.

These are perfectly fine starting points, better, in some cases, than whatever you’d have hoped for in the best scenario. What advantage do you derive from someone being polite? Or pulling their punches? Behind the behaviors that provoke an immediate negative reaction is opportunity—some exposed benefit that we can seize mentally and then act upon.

No one is talking glass-half-full-style platitudes here. This must be a complete flip. Seeing through the negative, past its underside, and into its corollary: the positive.

The demand on you is this: 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. A clearer head makes for steadier hands. And then those hands must be put to work. Good use.

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?

And it’s sad that so many of us fail—opting away from action. Because action is natural, innate. You trip and fall right now, your body’s instincts protect you. You extend your hands to break your fall, so you don’t break your face. In a vicious accident, you go into shock but still manage to get your arms up around your face. That’s where the term defensive wounds comes from. We don’t think, we don’t complain, we don’t argue. We act. We have real strength—more strength than we know.

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

Life can be frustrating. Oftentimes we know what our problems are. We may even know what to do about them. But we fear that taking action is too risky, that we don’t have the experience or that it’s not how we pictured it or because it’s too expensive, because it’s too soon, because we think something better might come along, because it might not work.

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

For some reason, these days we tend to downplay the importance of aggression, of taking risks, of barreling forward. It’s probably because it’s been negatively associated with certain notions of violence or masculinity.

So when you’re frustrated in pursuit of your own goals, don’t sit there and complain that you don’t have what you want or that this obstacle won’t budge. If you haven’t even tried yet, then of course you will still be in the exact same place. You haven’t actually pursued anything.

The thing standing in your way isn’t going anywhere. You’re not going to outthink it or outcreate it with some world-changing epiphany. You’ve got to look at it and the people around you, who have begun their inevitable chorus of doubts and excuses, and say, as Margaret Thatcher famously did: “You turn if you want to. The lady’s not for turning.”

politics and drama of working with a group? Once you start attacking an obstacle, quitting is not an option. It cannot enter your head. Abandoning one path for another that might be more promising? Sure, but that’s a far cry from giving up. Once you can envision yourself quitting altogether, you might as well ring the bell. It’s done. Consider this mind-set. never in a hurry never worried never desperate never stopping short

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.

In other words: It’s supposed to be hard. Your first attempts aren’t going to work. It’s going to take a lot out of you—but energy is an asset we can always find more of. It’s a renewable resource. 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.

When people ask where we are, what we’re doing, how that “situation” is coming along, the answer should be clear: We’re working on it. We’re getting closer. When setbacks come, we respond by working twice as hard.

Instead, they release their “Minimum Viable Product” (MVP)—the most basic version of their core idea with only one or two essential features.

But it’s no joke. Failure really can be an asset if what you’re trying to do is improve, learn, or do something new. It’s the preceding feature of nearly all successes. There’s nothing shameful about being wrong, about changing course. Each time it happens we have new options. Problems become opportunities.

When failure does come, ask: What went wrong here? What can be improved? What am I missing? This helps birth alternative ways of doing what needs to be done, ways that are often much better than what we started with. Failure puts you in corners you have to think your way out of. It is a source of breakthroughs.

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

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.

People fail in small ways all the time. But they don’t learn. They don’t listen. They don’t see the problems that failure exposes. It doesn’t make them better.

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

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.”

It says: Okay, you’ve got to do something very difficult. Don’t focus on that. Instead break it down into pieces. Simply do what you need to do right now. And do it well. And then move on to the next thing. Follow the process and not the prize.

The process is about finishing. Finishing games. Finishing workouts. Finishing film sessions. Finishing drives. Finishing reps. Finishing plays. Finishing blocks. Finishing the smallest task you have right in front of you and finishing it well.

And when you really get it right, even the hardest things become manageable. Because the process is relaxing. Under its influence, we needn’t panic. Even mammoth tasks become just a series of component parts.

That may seem almost too simple. But envision, a master practicing an exceedingly difficult craft and making it look effortless. There’s no strain, no struggling. So relaxed. No exertion or worry. Just one clean movement after another. That’s a result of the process.

The unordered mind loses track of what’s in front of it—what matters—and gets distracted by thoughts of the future. The process is order, it keeps our perceptions in check and our actions in sync.

Being trapped is just a position, not a fate.

forgetting all about B through Y. We want to have goals, yes, so everything we do can be in the service of something purposeful.

When we get distracted, when we start caring about something other than our own progress and efforts, the process is the helpful, if occasionally bossy, voice in our head. It is the bark of the wise, older leader who knows exactly who he is and what he’s got to do: Shut up. Go back to your stations and try to think about what we are going to do ourselves instead of worrying about what’s going on out there. You know what your job is. Stop jawing and get to work. The process is the voice that demands we take responsibility and ownership. That prompts us to act even if only in a small way. Like a relentless machine, subjugating resistance each and every way it exists, little by little. Moving forward, one step at a time. Subordinate strength to the process. Replace fear with the process. Depend on it. Lean on it. Trust in it. Take your time, don’t rush. Some problems are harder than others. Deal with the ones right in front of you first. Come back to the others later. You’ll get there. The process is about doing the right things, right now. Not worrying about what might happen later, or the results, or the whole picture.