#StoicWeek: 10 Strategies for Turning Obstacles Into Opportunities

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

(Photo: Pexels)
(Photo: Pexels)

There is an old Zen story about a king whose people had grown soft and entitled. Dissatisfied with this state of affairs, he hoped to teach them a lesson. His plan was simple: He would place a large boulder in the middle of the main road, completely blocking entry into the city. He would then hide nearby and observe their reactions.

Sign Up For Our Daily Newsletter

By clicking submit, you agree to our <a href="http://observermedia.com/terms">terms of service</a> and acknowledge we may use your information to send you emails, product samples, and promotions on this website and other properties. You can opt out anytime.

See all of our newsletters

How would they respond? Would they band together to remove it? Or would they get discouraged, quit, and return home?

With growing disappointment, the king watched as subject after subject came to this impediment and turned away. Or, at best, tried halfheartedly before giving up. Many openly complained or cursed the king or fortune or bemoaned the in- convenience, but none managed to do anything about it.

After several days, a lone peasant came along on his way into town. He did not turn away. Instead he strained and strained, trying to push it out of the way. Then an idea came to him: He scrambled into the nearby woods to find some- thing he could use for leverage. Finally, he returned with a large branch he had crafted into a lever and deployed it to dislodge the massive rock from the road.

Beneath the rock were a purse of gold coins and a note from the king, which said:

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

What if you had the ability to flip your obstacles and turn them into opportunities?

Here are 10 historical strategies for doing just that—practiced by great men and women throughout the centuries.

Strategy 1: Alter Your Perspective

Man does not simply exist but always decides what his existence will be, what he will become the next moment. — Viktor Frankl

We chose how we look at things. How we approach an obstacle determines how daunting it will be to overcome.

By controlling our irrational emotions, we are able to see thing as they are, not as we perceive them to be.

Think of it as selective editing—not to deceive others, but to properly orient ourselves.

Where the head goes, the body follows. Perception precedes action. Right action follows the right perspective.

Strategy 2: Flip The Obstacle On Its Head

There is good in everything, if only we look for it.— Laura Ingalls Wilder

The events that we initially perceive as negative all contain a positive, exposed benefit that we can recognize and act on.

A computer glitch that destroys your work is now a means to make it twice as good because you’re better prepared.

Having a terrible boss is now an opportunity to learn from his faults while you fill up your resume and look for better jobs elsewhere.

Notice this is a complete mental flip: Seeing through the negative, past its underside and through to the positive.

Strategy 3: Stay Moving, Always.

We must all either wear out or rust out, every one of us. My choice is to wear out. — Theodore Roosevelt

Those who attack problems and life with most initiative and energy usually win.

Courage is really just taking action. Start by saying yes to create momentum and you’ll be on your way.

Obstacles seem more intimidating when we stop to look up at them.

Strategy 4: Fail Cheaply and Quickly

What is defeat? Nothing but education; nothing but the first steps to something better. —Wendell Phillips

Engineers now like to quip: Failure is a Feature.

There’s nothing wrong with being wrong. Each time it happens, new options open up to us and problems can be flipped into opportunities.

When failure does come ask: Why did this happen? This helps birth alternative ways of doing what needs to be done. Failure puts you in corners you have to think your way out of and is a source of breakthroughs.

Strategy 5: Follow The Process

Under the comb the tangle and the straight path are the same. — Heraclitus

In the chaos of life, process provides us a way.

For whatever obstacles you come across, take a breath, do the immediate, composite part in front of you—and follow its thread into the next action.

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

Strategy 6: What’s Right Is What Works

I don’t care if the cat is black or white, so long as it catches mice. — Deng Xiaoping

We spend a lot of time thinking about how things are supposed to be.

As they say in Brazilian jiu-jitsu, it doesn’t matter how you get our opponent to the ground, only that you take them down.

Start thinking like a radical pragmatist: not on changing the world right at this moment,but ambitious enough to get everything you need.

Think progress, not perfection.

Strategy 7: Use The Flank Attack

Where little danger is apprehended, the more the enemy will be unprepared and consequently there is the fairest prospect of success. — George Washington

Think about this: In a study of more than 280 military campaigns, only two percent were decided on a direct attack on the enemy’s main army.

Being overmatched don’t have to be a disadvantage. It forces us to find workarounds, instead of challenging our enemy head on.

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

Strategy 8: Use The Obstacle Against Itself

Wise men are able to make a fitting use even of their enemies. — Plutarch

Action has many definitions. Sometimes you overcome obstacles not by attacking them but by withdrawing and letting them attack you.

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.

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

Strategy 9: Seize The Offensive

The best men are not those who have waited for chances but who have taken them; besieged chance, conquered the change, and made chance the servitor. — E.H. Chapin

Ordinary people shy away from negative situations and avoid trouble. What great people do is the opposite.

They never waste an opportunity to flip a personal tragedy or crisis to their advantage.

At certain moments in our brief existences we are faced with great trials. We must see that this “problem” presents an opportunity for a solution that we have long been waiting for.

It is in these moments that we must seize the offensive, because it is when people least expect it that we can pull off our biggest victories.

Strategy 10: Focus On Something Bigger Than Yourself

A man’s job is to make the world a better place to live in, so far as he is able—always remembering the results will be infinitesimal—and to attend to his own soul. — Leroy Percy

Sometimes when we are personally stuck with some impossible problem, one of the best ways to create opportunities or new avenues for movement is to think:

If I can’t solve this for myself, how can I at least make this better for other people?

You’ll be shocked by how much of the hopelessness lifts when we reach that conclusion—the strength that comes by thinking of people other than yourself.

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

So when you’re frustrated in pursuit of your own goals, don’t sit there and complain that you don’t have what you want or that this obstacle won’t budge. If you haven’t even tried yet, then of course you will still be in the exact same place. You haven’t actually pursued anything.

All the greats we admire started by saying, Yes, let’s go. And they usually did it in less desirable circumstances than we’ll ever suffer.

Just because the conditions aren’t exactly to your liking, or you don’t feel ready yet, doesn’t mean you get a pass. If you want momentum, you’ll have to create it yourself, right now, by getting up and getting started.

Ryan Holiday is the best-selling author of The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph. Ryan is an editor-at-large for the Observer, and he lives in Austin, Texas.

He’s also put together this list of 15 books that you’ve probably never heard of that will alter your worldview, help you excel at your career and teach you how to live a better life.

#StoicWeek: 10 Strategies for Turning Obstacles Into Opportunities