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

by Ryan Holiday

Certain things in life will cut you open like a knife. When that happens—at that exposing moment—the world gets a glimpse of what’s truly inside you. So what will be revealed when you’re sliced open by tension and pressure? Iron? Or air? Or bullshit?

“Theodore, you have the mind but haven’t got the body. I’m giving you the tools to make your body. It’s going to be hard drudgery and I think you have the determination to go through with it.”

Not everyone accepts their bad start in life. They remake their bodies and their lives with activities and exercise. They prepare themselves for the hard road. Do they hope they never have to walk it? Sure. But they are prepared for it in any case. Are you?

To Roosevelt, life was like an arena and he was a gladiator. In order to survive, he needed to be strong, resilient, fearless, ready for anything. And he was willing to risk great personal harm and expend massive amounts of energy to develop that hardiness.

A premortem is different. In it, we look to envision what could go wrong, what will go wrong, in advance, before we start. Far too many ambitious undertakings fail for preventable reasons. Far too many people don’t have a backup plan because they refuse to consider that something might not go exactly as they wish.

Because sometimes the only answer to “What if . . .” is, It will suck but we’ll be okay.

The only guarantee, ever, is that things will go wrong. The only thing we can use to mitigate this is anticipation. Because the only variable we control completely is ourselves.

Jefferson just wasn’t a public speaker—that doesn’t make him less of a man for acknowledging it and acting accordingly.

It doesn’t always feel that way but constraints in life are a good thing. Especially if we can accept them and let them direct us. They push us to places and to develop skills that we’d otherwise never have pursued.

You don’t have to like something to master it—or to use it to some advantage. When the cause of our problem lies outside of us, we are better for accepting it and moving on. For ceasing to kick and fight against it, and coming to terms with it. The Stoics have a beautiful name for this attitude. They call it the Art of Acquiescence.

It is far easier to talk of the way things should be. It takes toughness, humility, and will to accept them for what they actually are. It takes a real man or woman to face necessity.

Unfortunately, we are often too greedy to do this. We instinctively think about how much better we’d like any given situation to be. We start thinking about what we’d rather have. Rarely do we consider how much worse things could have been.

It’s time to be humble and flexible enough to acknowledge the same in our own lives. That there is always someone or something that could change the plan. And that person is not us. As the saying goes, “Man proposes but God disposes.

Because (a) you’re robust and resilient enough to handle whatever occurs, (b) you can’t do anything about it anyway, and (c) you’re looking at a big-enough picture and long-enough time line that whatever you have to accept is still only a negligible blip on the way to your goal. We’re indifferent and that’s not a weakness.

To do great things, we need to be able to endure tragedy and setbacks. We’ve got to love what we do and all that it entails, good and bad. We have to learn to find joy in every single thing that happens.

The next step after we discard our expectations and accept what happens to us, after understanding that certain things—particularly bad things—are outside our control, is this: loving whatever happens to us and facing it with unfailing cheerfulness.

Your obstacle may not be so serious or violent. But they are nevertheless significant and outside your control. They warrant only one response: a smile.

You love it because it’s all fuel. And you don’t just want fuel. You need it. You can’t go anywhere without it. No one or no thing can. So you’re grateful for it.

Persistence. Everything directed at one problem, until it breaks.

If persistence is attempting to solve some difficult problem with dogged determination and hammering until the break occurs, then plenty of people can be said to be persistent. But perseverance is something larger. It’s the long game. It’s about what happens not just in round one but in round two and every round after—and then the fight after that and the fight after that, until the end.

Life is not about one obstacle, but many. What’s required of us is not some shortsighted focus on a single facet of a problem, but simply a determination that we will get to where we need to go, somehow, someway, and nothing will stop us.

If our young men miscarry in their first enterprises, they lose all heart. If the young merchant fails, men say he is ruined. If the finest genius studies at one of our colleges, and is not installed in an office within one year afterwards in the cities or suburbs of Boston or New York, it seems to his friends and to himself that he is right in being disheartened, and in complaining the rest of his life.

We’d be so much better following the lead of Emerson’s counterexample. Someone who is willing to try not one thing, but “tries all the professions, who teams it, farms it, peddles, keeps a school, preaches, edits a newspaper, goes to Congress, buys a township, and so forth, in successive years, and always, like a cat, falls on his feet.”

Emerson said, “with the exercise of self-trust, new powers shall appear.”

Determination, if you think about it, is invincible. Nothing other than death can prevent us from following

The true threat to determination, then, is not what happens to us, but us ourselves. Why would you be your own worst enemy? Hold on and hold steady.

So he set up a network of support inside the camp, specifically to help soldiers who felt ashamed for having broken under the pressure. We’re in this together, he told them. He gave them a watchword to remind them: U.S.—Unity over Self.

People are getting a little desperate. People might not show their best elements to you. You must never lower yourself to being a person you don’t like. There is no better time than now to have a moral and civic backbone. To have a moral and civic true north. This is a tremendous opportunity for you, a young person, to be heroic.

Not that you need to martyr yourself. See, when we focus on others, on helping them or simply providing a good example, our own personal fears and troubles will diminish.

The desire to quit or compromise on principles suddenly feels rather selfish when we consider the people who would be affected by that decision. When it comes to obstacles and whatever reactions they provoke—boredom, hatred, frustration, or confusion—just because you feel that way, doesn’t mean everyone else does. Sometimes

What doesn’t help anyone is making this all about you, all the time. Why did this happen to me? What am I going to do about this?

Pride can be broken. Toughness has its limits. But a desire to help? No harshness, no deprivation, no toil should interfere with our empathy toward others. Compassion is always an option. Camaraderie as well. That’s a power of the will that can never be taken away, only relinquished.

You can always remember that a decade earlier, a century earlier, a millennium earlier, someone just like you stood right where you are and felt very similar things, struggling with the very same thoughts. They had no idea that you would exist, but you know that they did. And a century from now, someone will be in your exact same position, once more.

Be strong for them, and it will make you stronger.

Death doesn’t make life pointless, but rather purposeful.

Memento mori, the Romans would remind themselves. Remember you are mortal.

Remember the serenity prayer: If something is in our control, it’s worth every ounce of our efforts and energy. Death is not one of those things—it is not in our control how long we will live or what will come and take us from life.

But thinking about and being aware of our mortality creates real perspective and urgency. It doesn’t need to be depressing. Because it’s invigorating.

We can learn to adjust and come to terms with death—this final and most humbling fact of life—and find relief in the understanding that there is nothing else nearly as hard left.

Life is a process of breaking through these impediments—a series of fortified lines that we must break through. Each time, you’ll learn something. Each time, you’ll develop strength, wisdom, and perspective. Each time, a little more of the competition falls away. Until all that is left is you: the best version of you.

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. Get used to it and train accordingly.

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.

Not everyone looks at obstacles—often the same ones you and I face—and sees reason to despair. In fact, they see the opposite. They see a problem with a ready solution. They see a chance to test and improve themselves.