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

by Ryan Holiday

businesses and teams and people can take seemingly impossible situations and find ways to triumph over them.

loads made lighter for those who can apply the right pressure.”

What I understand today is that when the Stoics said that there was an opportunity in every obstacle, what they meant was the opportunity to practice virtue. To be a good person despite the bad things that have happened. To do good in the world despite the bad that has befallen you. They were speaking of the idea of arete. Excellence—in all forms.

What they meant when they said that the obstacle is the way is that the hardest, most heartbreaking moments of life can be transformed by endurance, by selflessness, by courage, by kindness, by decency.

“A writer—and, I believe, generally all persons—must think that whatever happens to him or her is a resource,” the great Jorge Luis Borges once explained.

“All things have been given to us for a purpose, and an artist must feel this more intensely. All that happens to us, including our humiliations, our misfortunes, our embarrassments, all is given to us as raw material, as clay, so that we may shape our art.”

Our experiences become the fuel for w...

It doesn’t matter how awful, how unfair, how expensive an experience is, I’ve come to understand that I have the greatest job in the world in that I can take what happens to me, even heartbreak, and turn it into material. In this way, noth...

For that’s what Stoicism is—a great conversation that stretches back thousands of years. Men and women talking to themselves, talking themselves through obstacles and opportunities, big moments and small ones, reminding themselves to be excellent, to follow virtue, to do what is demanded of them.

A formula for thriving not just in spite of whatever happens but because of it.

Our actions may be impeded…but there can be no impeding our intentions or dispositions. Because we can accommodate and adapt. The mind adapts and converts to its own purposes the obstacle to our acting.

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

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.

On the battlefield or in the boardroom, across oceans and many centuries, members of every group, gender, class, cause, and business have had to confront obstacles and struggle to overcome them—learning to turn those obstacles upside down.

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

Are you worthy? Can you get past the things that inevitably fall in your way? Will you stand up and show us what you’re made of?

That the challenge makes them better than if they’d never faced the adversity at all.

“Bad companies are destroyed by crisis,” he said. “Good companies survive them. Great companies are improved by them.”

What if you could turn every obstacle into an advantage? What if you could use each one to become who you were meant to become in that moment?

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.

Today, most of our obstacles are internal, not external.

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. But it’s worth it, for what’s left is truth.

He was inclined to see the opportunity in every disaster.

He had the strength to resist temptation or excitement, no matter how seductive, no matter the situation.

This insight lives on today in Warren Buffett’s famous adage to “be fearful when others are greedy and greedy when others are fearful.”

Rockefeller, like all great investors, could resist impulse in favor of cold, hard common sense.

He was resilient, adaptable, calm, always growing, hard to pin down.

He could not be rattled—not by economic crisis, not by a glittery mirage of false opportunities, not by aggressive, bullying enemies, not even by federal prosecutors (for whom he was a notoriously difficult witness to cross-examine, never rising to take the bait or defend himself or get upset).

“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 a half years of apprenticeship and the difficulties to be overcome, all along the way.”

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. You will learn that this reaction determines how successful we will be in overcoming—or possibly thriving because of—them.

Desperation, despair, fear, powerlessness—these reactions are functions of our perceptions.

To perceive what others see as negative, as something to be approached rationally, clearly, and, most important, as an opportunity—not as something to fear or bemoan.

What’s contained within a circumstance, what we can turn it into, is what matters.

We can stop seeing the “problems” in front of us as problems.

Discipline in perception lets you clearly see the advantage and the proper course of action in every situation—without the pestilence of panic or fear.

“The greatest empire,” Seneca—an adviser to emperors and a wealthy man himself—would say, “is command of yourself.”

We can learn to see all things rationally. Or better, like Rockefeller, we can see opportunity everywhere, including in disaster, and transform negative situations into an education, a skill set, or a fortune.

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

he would not be treated like a prisoner—because he was not powerless.

Whether they threw him in prison or threw him in solitary confinement for weeks on end, Carter maintained that he still had choices, choices that could not be taken from him even though his physical freedom had been.

They can throw us in jail, label us, deprive us of our possessions, but they’ll never control our thoughts, our beliefs, our reactions.

Even in prison, deprived of nearly everything, some freedoms remain. Your mind remains your own (if you’re lucky, you have books) and you have time—lots of time.

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

If an unjust prison sentence can be not only salvaged but transformative and beneficial, then for our purposes, nothing we’ll experience is likely without potential benefit.

“There is nothing either good or bad, but thinking makes it so,” as Shakespeare put it.

Or, with a shift in perception, it can be exactly what you were looking for—the chance to pierce through defenses and teach a lesson that can be learned only by experience. A mistake becomes training.

With one approach you took advantage; with the other you succumbed to anger or fear.