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

by Ryan Holiday

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The impediment to action advances action. What stands in the way becomes the way.

In Marcus’s words is the secret to an art known as turning obstacles upside down. To act with “a reverse clause,” so there is always a way out or another route to get to where you need to go. So that setbacks or problems are always expected and never permanent. Making certain that what impedes us can empower us.

And from what we know, he truly saw each and every one of these obstacles as an opportunity to practice some virtue: patience, courage, humility, resourcefulness, reason, justice, and creativity.

Whatever we face, we have a choice: Will we be blocked by obstacles, or will we advance through and over them?

Let’s be honest: Most of us are paralyzed. Whatever our individual goals, most of us sit frozen before the many obstacles that lie ahead of us.

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

We blame our bosses, the economy, our politicians, other people, or we write ourselves off as failures or our goals as impossible. When really only one thing is at fault: our attitude and approach.

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.

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.

I want to show you the way to turn every obstacle into an advantage.

It’s not just: How can I think this is not so bad? No, it is how to will yourself to see that this must be good—an opportunity to gain a new foothold, move forward, or go in a better direction. Not “be positive” but learn to be ceaselessly creative and opportunistic.

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

“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. Abundance can be its own obstacle, as many people can attest.

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

While others are excited or afraid, we will remain calm and imperturbable. We will see things simply and straightforwardly, as they truly are—neither good nor bad. This will be an incredible advantage for us in the fight against obstacles.

Rockefeller had sangfroid: unflappable coolness under pressure. He could keep his head while he was losing his shirt. Better yet, he kept his head while everyone else lost theirs.

It was this intense self-discipline and objectivity that allowed Rockefeller to seize advantage from obstacle after obstacle in his life, during the Civil War, and the panics of 1873, 1907, and 1929. As he once put it: He was inclined to see the opportunity in every disaster. To that we could add: He had the strength to resist temptation or excitement, no matter how seductive, no matter the situation.

You will come across obstacles in life—fair and unfair. And you will discover, time and time again, that what matters most is not what these obstacles are but how we see them, how we react to them, and whether we keep our composure.

Nothing makes us feel this way; we choose to give in to such feelings. Or, like Rockefeller, choose not to.

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.

We have a choice about how we respond to this situation (or any situation, for that matter). We can be blindly led by these primal feelings or we can understand them and learn to filter them.

Seen properly, everything that happens—be it an economic crash or a personal tragedy—is a chance to move forward. Even if it is on a bearing that we did not anticipate.

Choose not to be harmed—and you won’t feel harmed. Don’t feel harmed—and you haven’t been. —MARCUS AURELIUS

It took nineteen years and two trials to overturn that verdict, but when Carter walked out of prison, he simply resumed his life. No civil suit to recover damages, Carter did not even request an apology from the court. Because to him, that would imply that they’d taken something of his that Carter felt he was owed.

We decide what we will make of each and every situation. We decide whether we’ll break or whether we’ll resist. We decide whether we’ll assent or reject.

It’s how they turned prison into the workshop where they transformed themselves and the schoolhouse where they began to transform others.

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.

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.

A mistake becomes training

When we aim high, pressure and stress obligingly come along for the ride. Stuff is going to happen that catches us off guard, threatens or scares us. Surprises (unpleasant ones, mostly) are almost guaranteed. The risk of being overwhelmed is always there.

In these situations, talent is not the most sought-after characteristic. Grace and poise are, because these two attributes precede the opportunity to deploy any other skill.

There is always a countermove, always an escape or a way through, so there is no reason to get worked up. No one said it would be easy and, of course, the stakes are high, but the path is there for those ready to take it.

Because, as you now realize, it’s true. If your nerve holds, then nothing really did “happen”—our perception made sure it was nothing of consequence.

Welcome to the source of most of our problems down here on Earth. Everything is planned down to the letter, then something goes wrong and the first thing we do is trade in our plan for a good ol’ emotional freak-out. Some of us almost crave sounding the alarm, because it’s easier than dealing with whatever is staring us in the face.

Thus, the question for astronauts was not How skilled a pilot are you, but Can you keep an even strain? Can you fight the urge to panic and instead focus only on what you can change? On the task at hand?

Don’t let the negativity in, don’t let those emotions even get started. Just say: No, thank you. I can’t afford to panic.

As Gavin de Becker writes in The Gift of Fear, “When you worry, ask yourself, ‘What am I choosing to not see right now?’ What important things are you missing because you chose worry over introspection, alertness or wisdom?”

You can always remind yourself: I am in control, not my emotions. I see what’s really going on here. I’m not going to get excited or upset.

Try having that conversation with yourself and see how those extreme emotions hold up. They won’t last long, trust that.

It might help to say it over and over again whenever you feel the anxiety begin to come on: I am not going to die from this. I am not going to die from this. I am not going to die from this.

Does what happened keep you from acting with justice, generosity, self-control, sanity, prudence, honesty, humility, straightforwardness?

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No, because I practiced for this situation and I can control myself. Or, No, because I caught myself and I’m able to realize that that doesn’t add anything constructive.

The observing eye sees events, clear of distractions, exaggerations, and misperceptions. The perceiving eye sees “insurmountable obstacles” or “major setbacks” or even just “issues.” It brings its own issues to the fight. The former is helpful, the latter is not.

Perceptions are the problem. They give us the “information” that we don’t need, exactly at the moment when it would be far better to focus on what is immediately in front of us: the thrust of a sword, a crucial business negotiation, an opportunity, a flash of insight or anything else, for that matter.

Epictetus told his students, when they’d quote some great thinker, to picture themselves observing the person having sex. It’s funny, you should try it the next time someone intimidates you or makes you feel

Objectivity means removing “you”—the subjective part—from the equation. Just think, what happens when we give others advice? Their problems are crystal clear to us, the solutions obvious. Something that’s present when we deal with our own obstacles is always missing when we hear other people’s problems: the baggage. With other people we can be objective.