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

by Ryan Holiday

This is what happens when you do your job—whatever it is—and do it well.

Everything we do matters—whether it’s making smoothies while you save up money or studying for the bar—even after you already achieved the success you sought. Everything is a chance to do and be your best. Only self-absorbed assholes think they are too good for whatever their current station requires.

To whatever we face, our job is to respond with: hard work honesty helping others as best we can

You should never have to ask yourself, But what am I supposed to do now? Because you know the answer: your job.

Jobs knew his marching orders: Respect the craft and make something beautiful.

The great psychologist Viktor Frankl, survivor of three concentration camps, found presumptuousness in the age-old question: “What is the meaning of life?” As though it is someone else’s responsibility to tell you. Instead, he said, the world is asking you that question. And it’s your job to answer with your actions.

Forget the rule book, settle the issue.

This is pragmatism embodied. Don’t worry about the “right” way, worry about the right way. This is how we get things done.

We spend a lot of time thinking about how things are supposed to be, or what the rules say we should do. Trying to get it all perfect. We tell ourselves that we’ll get started once the conditions are right, or once we’re sure we can trust this or that. When, really, it’d be better to focus on making due with what we’ve got. On focusing on results instead of pretty methods.

Scratch the complaining. No waffling. No submitting to powerlessness or fear. You can’t just run home to Mommy. How are you going to solve this problem? How are you going to get around the rules that hold you back?

Start thinking like a radical pragmatist: still ambitious, aggressive, and rooted in ideals, but also imminently practical and guided by the possible. Not on everything you would like to have, not on changing the world right at this moment, but ambitious enough to get everything you need. Don’t think small, but make the distinction between the critical and the extra. Think progress, not perfection. Under this kind of force, obstacles break apart. They have no choice. Since you’re going around them or making them irrelevant, there is nothing for them to resist.

From everywhere else. From the flanks. From the unexpected. From the psychological. From drawing opponents out from their defenses. From the untraditional. From anything but . . . As Hart writes in his masterwork Strategy: [T]he Great Captain will take even the most hazardous indirect approach—if necessary over mountains, deserts or swamps, with only a fraction of the forces, even cutting himself loose from his communications. Facing, in fact, every unfavorable condition rather than accept the risk of stalemate invited by direct approach.

Take a step back, then go around the problem. Find some leverage. Approach from what is called the “line of least expectation.”

What’s your first instinct when faced with a challenge? Is it to outspend the competition? Argue with people in an attempt to change long-held opinions? Are you trying to barge through the front door? Because the back door, side doors, and windows may have been left wide open.

Of course, when pushed, the natural instinct is always to push back. But martial arts teach us that we have to ignore this impulse. We can’t push back, we have to pull until opponents lose their balance. Then we make our move.

The art of the side-door strategy is a vast, creative space. And it is by no means limited to war, business, or sales.

You don’t convince people by challenging their longest and most firmly held opinions. You find common ground and work from there.

Remember, sometimes the longest way around is the shortest way home.

Sometimes you overcome obstacles not by attacking them but by withdrawing and letting them attack you. You can use the actions of others against themselves instead of acting yourself.

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.

Just ask the Russians, who defeated Napoléon and the Nazis not by rigidly protecting their borders but by retreating into the interior and leaving the winter to do their work on the enemy, bogged down in battles far from home.

So instead of fighting obstacles, find a means of making them defeat themselves.

We push and push—to get a raise, a new client, to prevent some exigency from happening. In fact, the best way to get what we want might be to reexamine those desires in the first place.

We wrongly assume that moving forward is the only way to progress, the only way we can win. Sometimes, staying put, going sideways, or moving backward is actually the best way to eliminate what blocks or impedes your path.

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?

The harder you fight, the less you’ll achieve (other than exhaustion). So it goes with our problems.

Adversity can harden you. Or it can loosen you up and make you better—if you let it.

If you think it’s simply enough to take advantage of the opportunities that arise in your life, you will fall short of greatness. Anyone sentient can do that. What you must do is learn how to press forward precisely when everyone around you sees disaster.

It’s at the seemingly bad moments, when people least expect it, that we can act swiftly and unexpectedly to pull off a big victory. While others are arrested by discouragement, we are not. We see the moment differently, and act accordingly.

You always planned to do something. Write a screenplay. Travel. Start a business. Approach a possible mentor. Launch a movement. Well, now something has happened—some disruptive event like a failure or an accident or a tragedy. Use it.

Perhaps you’re stuck in bed recovering. Well, now you have time to write. Perhaps your emotions are overwhelming and painful, turn it into material. You lost your job or a relationship? That’s awful, but now you can travel unencumbered. You’re having a problem? Now you know exactly what to approach that mentor about. Seize this moment to deploy the plan that has long sat dormant in your head. Every chemical reaction requires a catalyst. Let this be yours.

But this crisis in front of you? You’re wasting it feeling sorry for yourself, feeling tired or disappointed. You forget: Life speeds on the bold and favors the brave.

Great commanders look for decision points. For it is bursts of energy directed at decisive points that break things wide open. They press and press and press and then, exactly when the situation seems hopeless—or, more likely, hopelessly deadlocked—they press once more.

What we can’t do is control the world around us—not as much as we’d like to, anyway. We might perceive things well, then act rightly, and fail anyway.

WHAT IS WILL? Will is our internal power, which can never be affected by the outside world. It is our final trump card. If action is what we do when we still have some agency over our situation, the will is what we depend on when agency has all but disappeared.

Leadership requires determination and energy. And certain situations, at times, call on leaders to marshal that determined energy simply to endure.

This is the avenue for the final discipline: the Will. If Perception and Action were the disciplines of the mind and the body, then Will is the discipline of the heart and the soul. The will is the one thing we control completely, always. Whereas I can try to mitigate harmful perceptions and give 100 percent of my energy to actions, those attempts can be thwarted or inhibited. My will is different, because it is within me.

Lincoln was strong and decisive as a leader. But he also embodied the Stoic maxim: sustine et abstine. Bear and forbear. Acknowledge the pain but trod onward in your task.

These lessons come harder but are, in the end, the most critical to wresting advantage from adversity. In every situation, we can Always prepare ourselves for more difficult times. Always accept what we’re unable to change. Always manage our expectations. Always persevere. Always learn to love our fate and what happens to us. Always protect our inner self, retreat into ourselves. Always submit to a greater, larger cause. Always remind ourselves of our own mortality.

And, of course, prepare to start the cycle once more.

We craft our spiritual strength through physical exercise, and our physical hardiness through mental practice (mens sana in corpore sano—sound mind in a strong body).

This is strikingly similar to what the Stoics called the Inner Citadel, that fortress inside of us that no external adversity can ever break down.

An important caveat is that we are not born with such a structure; it must be built and actively reinforced. During the good times, we strengthen ourselves and our bodies so that during the difficult times, we can depend on it. We protect our inner fortress so it may protect us.

To be great at something takes practice. Obstacles and adversity are no different. Though it would be easier to sit back and enjoy a cushy modern life, the upside of preparation is that we’re not disposed to lose all of it—least of all our heads—when someone or something suddenly messes with our plans.

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.

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. What if . . . Then I will . . . What if . . . Instead I’ll just . . . What if . . . No problem, we can always . . .

If this comes as a constant surprise each and every time it occurs, you’re not only going to be miserable, you’re going to have a much harder time accepting it and moving on to attempts number two, three, and four. 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. 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.

The world might call you a pessimist. Who cares? 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.

We are prepared for failure and ready for success.

After you’ve distinguished between the things that are up to you and the things that aren’t (ta eph’hemin, ta ouk eph’hemin), and the break comes down to something you don’t control . . . you’ve got only one option: acceptance.