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

by Ryan Holiday

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.

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

Great individuals, like great companies, find a way to transform weakness into strength.

The market was inherently unpredictable and often vicious—only the rational and disciplined mind could hope to profit from it. Speculation led to disaster, he realized, and he needed to always ignore the “mad crowd” and its inclinations.

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).

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.

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.

Opposites work. Nonaction can be action. It uses the power of others and allows us to absorb their power as our own. Letting them—or the obstacle—do the work for us.

Instead of fighting the obstacle, you try to use its energy to your advantage—you see what you can get for free from it. That they underestimate you? That they attacked you and made you sympathetic? That they ignored you entirely? That the tough market has eliminated a lot of the competition? These are all things you’ve gotten for free, things that direct us toward various strategies, things we can be thankful for and use.

There is a famous story of Alexander the Great and a famously difficult horse named Bucephalus—a horse that even his father, King Philip II of Macedon, could not break. While others had tried sheer force and whips and ropes, a young Alexander succeeded by lightly mounting and simply hanging onto the racing and wild animal until the horse was calm. Having exhausted himself, Bucephalus finally submitted to his rider’s influence. Alexander, having taken Bucephalus’s energy and used it against him, would ride into battle on that faithful horse for the next twenty years. Now what of your obstacles? Yes, sometimes we need to learn from Amelia Earhart and just take action. But we also have to be ready to see that restraint might be the best action for us to take. Gandhi’s campaign against bigotry and the British lasted for decades—more often than not, he was reining in his supporters instead of spurring them toward some decisive action. He understood it would take time for the British to beat themselves, for public opinion to be changed by each mistake he baited them into.

Sometimes in your life you need to have patience—wait for temporary obstacles to fizzle out. Let two jousting egos settle things between themselves instead of jumping immediately into the fray. Sometimes a problem needs less of you—fewer people period—and not more. When we want things too badly we can be our own worst enemy. In our eagerness, we strip the very screw we want to turn and make it impossible to ever get what we want. We spin our tires in the snow or mud and dig a deeper rut—one that we’ll never get out of. We get so consumed with moving forward that we forget that th...

There is a certain humility required in the approach. It means accepting that the way you originally wanted to do things is not possible. You just haven’t got it in you to do it the “traditional” way. But so what? What matters is whether a certain approach gets you to where you want to go. And let’s be clear, using obstacles against themselves is very different from doing nothing. Passive resistance is, in fact, incredibly active. But those actions come in the form of discipline, self-control, fearlessness, determination, and grand strategy. The great strategist Saul Alinsky believed that if you “push a negative hard enough and deep enough it will break through into its counterside.” Every positive has its negative. Every negative has its positive. The action is in the pushing through—all the way through to the other side. Making a negative into a positive.

When jarred, unavoidably, by circumstance, revert at once to yourself, and don’t lose the rhythm more than you can help. You’ll have a better grasp of harmony if you keep going back to it. —Marcus Aurelius

The best men are not those who have waited for chances—but taken them, besieged the chance, conquered the chance, and made the chance their servitor. —E. H. Chapin In the spring of 2008, Barack

Ordinary people shy away from negative situations, just as they do with failure. They do their best to avoid trouble. What great people do is the opposite. They are their best in these situations. They turn personal tragedy or misfortune—really anything, everything—to their advantage.

Life speeds on the bold and favors the brave.

You are invincible if nothing outside the will can disconcert you. —Epictetus

It’s almost a cliché at this point, but the observation that the way to strengthen an arch is to put weight on it—because it binds the stones together, and only with tension does it hold weight—is a great metaphor. The path of least resistance is a terrible teacher. We can’t afford to shy away from the things that intimidate us. We don’t need to take our weaknesses for granted.

Are you okay being alone? Are you strong enough to go a few more rounds if it comes to that? Are you comfortable with challenges? Does uncertainty bother you? How does pressure feel?

It’s your armor plating. It doesn’t make you invincible, but it helps prepare you for when fortune shifts…and it always does.

The credit goes to the Stoics. They even had a better name: premeditatio malorum (premeditation of evils).

If it can happen, it will. Are you ready for when it happens to you?

Always prepared for disruption, always working that disruption into our plans. Fitted, as they say, for defeat or victory. And let’s be honest, a pleasant surprise is a lot better than an unpleasant one.

And in the case where nothing could be done, the Stoics would use it as an important practice to do something the rest of us too often fail to do: manage expectations. Because sometimes the only answer to “What if…” is, It will suck but we’ll be okay. We’ll endure it. We won’t be broken by it.

“Offer a guarantee and disaster threatens” went the inscription at the Oracle of Delphi. Be humble. Be prepared.

Common wisdom provides us with the maxims: Beware the calm before the storm. Hope for the best, prepare for the worst. The worst is yet to come.

It gets worse before it gets better. It always takes longer than you expect…even when you take this into account.

It’s far better to seem like a downer than to be blindsided or caught off guard. It’s better to meditate on what could happen, to probe for weaknesses in our plans, so those inevitable failures can be correctly perceived, appropriately addressed, or simply endured.