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

by Ryan Holiday

How skilled we are at cataloging what holds us back!

Every obstacle is unique to each of us. But the responses they elicit are the same: Fear. Frustration. Confusion. Helplessness. Depression. Anger.

On the other hand, not everyone is paralyzed. We watch in awe as some seem to turn those very obstacles, which stymie us, into launching pads for themselves. How do they do that? What’s the secret?

What do these figures have that we lack? What are we missing? It’s simple: a method and a framework for understanding, appreciating, and acting upon the obstacles life throws at us.

Andy Grove, former CEO of Intel, outlined when he described what happens to businesses in tumultuous times: “Bad companies are destroyed by crisis. Good companies survive them. Great companies are improved by them.”

Who lived the words of Marcus Aurelius and followed a group which Cicero called the only “real philosophers”—the ancient Stoics—even if they’d never read them.* They had the ability to see obstacles for what they were, the ingenuity to tackle them, and the will to endure a world mostly beyond their comprehension and control.

Rather, we face some minor disadvantage or get stuck with some less-than-favorable conditions. Or we’re trying to do something really hard and find ourselves outmatched, overstretched, or out of ideas. Well, the same logic applies. Turn it around. Find some benefit. Use it as fuel. It’s simple. Simple but, of course, not easy.

Not “be positive” but learn to be ceaselessly creative and opportunistic. Not: This is not so bad. But: I can make this good.

“The obstacle in the path becomes the path. Never forget, within every obstacle is an opportunity to improve our condition.”

But run down the list of those who came before you. Athletes who were too small. Pilots whose eyesight wasn’t good enough. Dreamers ahead of their time. Members of this race or that. Dropouts and dyslexics. Bastards, immigrants, nouveaux riches, sticklers, believers, and dreamers. Or those who came from nothing or worse, from places where their very existence was threatened on a daily basis. What happened to them? Well, far too many gave up. But a few didn’t. They took “twice as good” as a challenge. They practiced harder. Looked for shortcuts and weak spots. Discerned allies among strange faces. Got kicked around a bit. Everything was an obstacle they had to flip. And so?

When you have a goal, obstacles are actually teaching you how to get where you want to go—carving you a path. “The Things which hurt,” Benjamin Franklin wrote, “instruct.”

Instead of opposing enemies, we have internal tension. We have professional frustration. We have unmet expectations. We have learned helplessness. And we still have the same overwhelming emotions humans have always had: grief, pain, loss.

Many of our problems come from having too much: rapid technological disruption, junk food, traditions that tell us the way we’re supposed to live our lives. We’re soft, entitled, and scared of conflict. Great times are great softeners.

It begins with how we look at our specific problems, our attitude or approach; then the energy and creativity with which we actively break them down and turn them into opportunities; finally, the cultivation and maintenance of an inner will that allows us to handle defeat and difficulty. It’s three interdependent, interconnected, and fluidly contingent disciplines: Perception, Action, and the Will

It’s three interdependent, interconnected, and fluidly contingent disciplines: Perception, Action, and the Will.

It takes skill and discipline to bat away the pests of bad perceptions, to separate reliable signals from deceptive ones, to filter out prejudice, expectation, and fear.

“Oh, how blessed young men are who have to struggle for a foundation and beginning in life,” he once said. “I shall never cease to be grateful for the three and half years of apprenticeship and the difficulties to be overcome, all along the way.”

You must realize: Nothing makes us feel this way; we choose to give in to such feelings.

Too often we react emotionally, get despondent, and lose our perspective. All that does is turn bad things into really bad things. Unhelpful perceptions can invade our minds—that sacred place of reason, action and will—and throw off our compass.

There are a few things to keep in mind when faced with a seemingly insurmountable obstacle. We must try: To be objective To control emotions and keep an even keel To choose to see the good in a situation To steady our nerves To ignore what disturbs or limits others To place things in perspective To revert to the present moment To focus on what can be controlled This is how you see the opportunity within the obstacle.

In fact, if we have our wits fully about us, we can step back and remember that situations, by themselves, cannot be good or bad. This is something—a judgment—that we, as human beings, bring to them with our perceptions.

As for us, we face things that are not nearly as intimidating, and then we promptly decide we’re screwed. This is how obstacles become 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.

Just because your mind tells you that something is awful or evil or unplanned or otherwise negative doesn’t mean you have to agree.

never in a hurry never worried never desperate never stopping short

Epictetus: “persist and resist.”

It’s okay to be discouraged. It’s not okay to quit.

No! There are some things that you should definetely quit!

Edison once explained that in inventing, “the first step is an intuition—and comes with a burst—then difficulties arise.”

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.

What is defeat? Nothing but education; nothing but the first steps to something better. —WENDELL PHILLIPS

As engineers now like to quip: Failure is a Feature.

There’s nothing shameful about being wrong, about changing course. Each time it happens we have new options. Problems become opportunities.

Action and failure are two sides of the same coin. One doesn’t come without the other. What breaks this critical connection down is when people stop acting—because they’ve taken failure the wrong way.

The one way to guarantee we don’t benefit from failure—to ensure it is a bad thing—is to not learn from it.

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.

We can channel this, too. We needn’t scramble like we’re so often inclined to do when some difficult task sits in front of us. 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.

We shy away from writing a book or making a film even though it’s our dream because it’s so much work—we can’t imagine how we get from here to there.

This is what happens when you do your job—whatever it is—and do it well. These men went from humble poverty to power by always doing what they were asked to do—and doing it right and with real pride.

Sometimes, on the road to where we are going or where we want to be, we have to do things that we’d rather not do. Often when we are just starting out, our first jobs “introduce us to the broom,” as Andrew Carnegie famously put it. There’s nothing shameful about sweeping. It’s just another opportunity to excel—and to learn. But you, you’re so busy thinking about the future, you don’t take any pride in the tasks you’re given right now. You just phone it all in, cash your paycheck, and dream of some higher station in life. Or you think, This is just a job, it isn’t who I am, it doesn’t matter. Foolishness.

Wherever we are, whatever we’re doing and wherever we are going, we owe it to ourselves, to our art, to the world to do it well. That’s our primary duty. And our obligation. When action is our priority, vanity falls away.

Each project matters, and the only degrading part is giving less than one is capable of giving.

Whether anyone notices, whether we’re paid for it, whether the project turns out successfully—it doesn’t matter. We can and always should act with those three traits—no matter the obstacle.

Instead he would show new ways of looking at or understanding the world. 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.