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

by Ryan Holiday

Take your time, don’t rush. Some problems are harder than others. Deal with the ones right in front of you first.

The process is about doing the right things, right now. Not worrying about what might happen later, or the results,

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. And doing it better than anyone else. In fact, doing it well because no one else wanted to do it.

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.

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. Of course it does!

When action is our priority, vanity falls away.

An artist is given many different canvases and commissions in their lifetime, and what matters is that they treat each one as a priority.

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

Steve Jobs even cared about the inside of his products, making sure they were beautifully designed even though the users would never see them.

In every design predicament, Jobs knew his marching orders: Respect the craft and make something beautiful.

When we do things seriously, conscientiously, when we do them well, we’re saying: This matters. I matter. Life is meaningful.

It’s a way to turn every obstacle into an opportunity. It’s a chance to do great work in a crummy situation.

Because all we need to do is those three little duties—to try hard, to be honest, and to help others and ourselves.

But never forget that each individual instance matters, too—each is a snapshot of the whole. The whole isn’t certain, only the instances are.

How you do anything is how you can do everything.

Pragmatism is not so much realism as flexibility. There are a lot of ways to get from point A to point B. It doesn’t have to be a straight line. It’s just got to get you where you need to go. But so many of us spend so much time looking for the perfect solution that we pass up what’s right in front of us.

As Deng Xiaoping once said, “I don’t care if the cat is black or white, so long as it catches mice.”

Start thinking like a pragmatist: still ambitious, aggressive, and rooted in virtue but also imminently practical and guided by the possible.

Don’t think small, but make the distinction between the critical and the extra. Think progress, not perfection.

Take a step back, then go around the problem. Find some leverage. Approach from what is called the “line of least expectation.” The thing they thought was impossible. The thing everyone else was afraid to try. The thing that only you could do.

Part of the reason why a certain skill often seems so effortless for great masters is not just because they’ve mastered the process—they really are doing less than the rest of us who don’t know any better.

Being outnumbered, coming from behind, being low on funds, these don’t have to be disadvantages. They can be gifts. Assets that make us less likely to foolishly try a head-to-head attack. These things force us to be creative, to find work-arounds, to sublimate the ego and do anything to win besides challenging our enemies where they are strongest.

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.

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.

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.

The actress Kate Winslet, a seven-time Academy Award nominee despite lacking any classical training, once explained that her secret on camera was to ask herself the question, “What can I get for free?” Meaning, if she’s tired, she uses that in the character.

Instead of fighting the obstacle, you try to use its energy to your advantage—you see what you can get for free from it.

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.

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 get so consumed with moving forward that we forget that there are other ways to get where we are heading.

We push and push. We’re pushing 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. Or it might be to aim for something else entirely, and use the impediment as an opportunity to explore a new direction.

Or we might discover that in ignoring clients, we attract more—finding that they want to work with someone who does not so badly want to work with them. Or we rethink that disaster we feared (along with everyone else) and come up with a way to profit from it when and if it happens.

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.

Remember, a castle can be an intimidating, impenetrable fortress, or it can be turned into a prison when surrounded. The difference is simply a shift in action and approach. We can use the things that block us to our advantage, letting them do the difficult work for us. Sometimes this means leaving the obstacle as is, instead of trying so hard to change it.

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

Instead of giving in to frustration, we can put it to good use. It can power our actions, which become stronger and better when loose and bold. While others obsess over observing the rules, we’re subtly undermining them and subverting them to our advantage.

To be physically and mentally loose takes no talent. That’s just recklessness. (We want right action, not action period.)

To be physically and mentally tight? That’s called anxiety. It doesn’t work, either. Eventually we snap.

But physical looseness combined with mental restraint?...

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

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 because you’ve just had your heart broken. This is material. You lost your job? That’s awful, but now you can travel unencumbered.

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.

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.

Or more precisely, can we see that this “problem” presents an opportunity for a solution that we have long been waiting for?

The obstacle is not only turned upside down but used as a catapult.

We can turn every obstacle upside down, too, simply by using it as an opportunity to practice some other virtue or skill—even if it is just learning to accept that bad things happen, or practicing humility.