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

by Ryan Holiday

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

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. If what’s up to us is the playing field, then what is not up to us are the rules and conditions of the game. Factors that winning athletes make the best of and don’t spend time arguing against (because there is no point). To argue, to complain, or worse, to just give up, these are choices. Choices that more often than not, do nothing to get us across the finish line.

🙂 Nice to know about the Serenity Prayer. I’m always fascinated by timeless philosophy that’s poeticized, romanticized, or otherwise for modern consumption.

In its own way, the most harmful dragon we chase is the one that makes us think we can change things that are simply not ours to change.

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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. To see an obstacle as a challenge, to make the best of it anyway, that is also a choice—a choice that is up to us. Will I have a chance, Coach? Ta eph’hemin? Is this up to me?

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

Our understanding of the world of business is all mixed up with storytelling and mythology. Which is funny because we’re missing the real story by focusing on individuals. In fact, half the companies in the Fortune 500 were started during a bear market or recession. Half. 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. 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. 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.

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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.

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

Having learned early in life that reality was falsely hemmed in by rules and compromises that people had been taught as children, Jobs had a much more aggressive idea of what was or wasn’t possible. To him, when you factored in vision and work ethic, much of life was malleable.

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?

It’s one thing to not be overwhelmed by obstacles, or discouraged or upset by them. This is something that few are able to do. But after you have controlled your emotions, and you can see objectively and stand steadily, the next step becomes possible: a mental flip, so you’re looking not at the obstacle but at the opportunity within it. 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. When really, it’s all fair game, and every situation is an opportunity for us to act.

Sports psychologists recently did a study of elite athletes who were struck with some adversity or serious injury. Initially, each reported feeling isolation, emotional disruption, and doubts about their athletic ability. Yet afterward, each reported gaining a desire to help others, additional perspective, and realization of their own strengths. In other words, every fear and doubt they felt during the injury turned into greater abilities in those exact areas. It’s a beautiful idea. Psychologists call it adversarial growth and post-traumatic growth. “That which doesn’t kill me makes me stronger” is not a cliché but fact. 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.

Problems are rarely as bad as we think—or rather, they are precisely as bad as we think. It’s a huge step forward to realize that the worst thing to happen is never the event, but the event and losing your head. Because then you’ll have two problems (one of them unnecessary and post hoc).

WHAT IS ACTION? Action is commonplace, right action is not. As a discipline, it’s not any kind of action that will do, but 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. Our movements and decisions define us: We must be sure to act with deliberation, boldness, and persistence. Those are the attributes of right and effective action. Nothing else—not thinking or evasion or aid from others. Action is the solution and the cure to our predicaments.

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. When he did venture out, it was to learn even more. Every moment, every conversation, every transaction, was an opportunity for him to improve his art.

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.

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.

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.

We talk a lot about courage as a society, but we forget that at its most basic level it’s really just taking action—whether that’s approaching someone you’re intimidated by or deciding to finally crack a book on a subject you need to learn. 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.

Doing new things invariably means obstacles. A new path is, by definition, uncleared. Only with persistence and time can we cut away debris and remove impediments. Only in struggling with the impediments that made others quit can we find ourselves on untrodden territory—only by persisting and resisting can we learn what others were too impatient to be taught.

Edison once explained that in inventing, “the first step is an intuition—and comes with a burst—then difficulties arise.” What set Edison apart from other inventors is tolerance for these difficulties, and the steady dedication with which he applied himself toward solving them. 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.

It’s time you understand that the world is telling you something with each and every failure and action. It’s feedback—giving you precise instructions on how to improve, it’s trying to wake you up from your cluelessness. It’s trying to teach you something. Listen.

Being able to see and understand the world this way is part and parcel of overturning obstacles. Here, a negative becomes a positive. We turn what would otherwise be disappointment into opportunity. Failure shows us the way—by showing us what isn’t the way.

In the chaos of sport, as in life, process provides us a way. 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.

Excellence is a matter of steps.

Remember the first time you saw a complicated algebra equation? It was a jumble of symbols and unknowns. But then you stopped, took a deep breath, and broke it down. You isolated the variables, solved for them, and all that was left was the answer. Do that now, for whatever obstacles you come across. We can take a breath, do the immediate, composite part in front of us—and follow its thread into the next action. Everything in order, everything connected.

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.

There will never be any obstacles that can ever truly prevent us from carrying out our obligation—harder or easier challenges, sure, but never impossible. Each and every task requires our best.

In every design predicament, Jobs knew his marching orders: Respect the craft and make something beautiful.

The great psychologist Viktor Frankl, survivor of three concentration camps, found presumptuousness in the age-old question: “What is the meaning of life?” As though it is someone else’s responsibility to tell you. Instead, he said, the world is asking you that question. And it’s your job to answer with your actions. In every situation, life is asking us a question, and our actions are the answer. Our job is simply to answer well.

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Sure, the goal is important. But never forget that each individual instance matters, too—each is a snapshot of the whole. The whole isn’t certain, only the instances are. How you do anything is how you can do everything. We can always act right.

With the stakes this high, you better be willing to bend the rules or do something desperate or crazy. To thumb your nose at the authorities and say: What? This is not a bridge. I don’t know what you’re talking about. Or, in some cases, giving the middle finger to the people trying to hold you down and blowing right through their evil, disgusting rules.

Start thinking like a radical pragmatist: still ambitious, aggressive, and rooted in ideals, but also imminently practical and guided by the possible. Not on everything you would like to have, not on changing the world right at this moment, but ambitious enough to get everything you need. Don’t think small, but make the distinction between the critical and the extra. Think progress, not perfection. Under this kind of force, obstacles break apart. They have no choice. Since you’re going around them or making them irrelevant, there is nothing for them to resist.

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.

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Part of the reason why a certain skill often seems so effortless for great masters is not just because they’ve mastered the process—they really are doing less than the rest of us who don’t know any better. They choose to exert only calculated force where it will be effective, rather than straining and struggling with pointless attrition tactics.

You don’t convince people by challenging their longest and most firmly held opinions. You find common ground and work from there. Or you look for leverage to make them listen. Or you create an alternative with so much support from other people that the opposition voluntarily abandons its views and joins your camp. The way that works isn’t always the most impressive. Sometimes it even feels like you’re taking a shortcut or fighting unfairly. There’s a lot of pressure to try to match people move for move, as if sticking with what works for you is somehow cheating. Let me save you the guilt and self-flagellation: It’s not. You’re acting like a real strategist. You aren’t just throwing your weight around and hoping it works. You’re not wasting your energy in battles driven by ego and pride rather than tactical advantage. Believe it or not, this is the hard way. That’s why it works. Remember, sometimes the longest way around is the shortest way home.

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