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

by Ryan Holiday

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.

A mistake becomes training.

Just because your mind tells you that something is awful or evil or unplanned or otherwise negative doesn’t mean you have to agree.

When people panic, they make mistakes.

Fear is debilitating, distracting, tiring, and often irrational.

we are scared of obstacles because our perspective is wrong—that a simple shift in perspective can change our reaction entirely.

We choose how we’ll look at things. We retain the ability to inject perspective into a situation. We can’t change the obstacles themselves—that part of the equation is set—but the power of perspective can change how the obstacles appear. How we approach, view, and contextualize an obstacle, and what we tell ourselves it means, determines how daunting and trying it will be to overcome.

“ta eph’hemin, ta ouk eph’hemin.”

An entrepreneur is someone with faith in their ability to make something where there was nothing before.

“There is good in everything, if only we look for it.”

“That which doesn’t kill me makes me stronger”

The struggle against an obstacle inevitably propels the fighter to a new level of functioning. The extent of the struggle determines the extent of the growth. The obstacle is an advantage, not adversity. The enemy is any perception that prevents us from seeing this.

In life, it doesn’t matter what happens to you or where you came from. It matters what you do with what happens and what you’ve been given.

Life can be frustrating. Oftentimes we know what our problems are. We may even know what to do about them. But we fear that taking action is too risky, that we don’t have the experience or that it’s not how we pictured it or because it’s too expensive, because it’s too soon, because we think something better might come along, because it might not work.

You’ve got to start, to go anywhere.

Persist in your efforts. Resist giving in to distraction, discouragement, or disorder.

It’s okay to be discouraged. It’s not okay to quit.

Failure really can be an asset if what you’re trying to do is improve, learn, or do something new.

Our capacity to try, try, try is inextricably linked with our ability and tolerance to fail, fail, fail.

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.

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

Think progress, not perfection.

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.

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.

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

When we want things too badly we can be our own worst enemy.

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.

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

In every situation, that which blocks our path actually presents a new path with a new part of us.

Problems, as Duke Ellington once said, are a chance for us to do our best.

We must prepare for adversity and turmoil, we must learn the art of acquiescence and practice cheerfulness even in dark times.

True will is quiet humility, resilience, and flexibility; the other kind of will is weakness disguised by bluster and ambition.

Leadership requires determination and energy.

determined energy simply to endure. To provide strength in terrible times.

If Perception and Action were the disciplines of the mind and the body, then Will is the discipline of the heart and the soul.

Nobody is born with a steel backbone. We have to forge that ourselves.

To do great things, we need to be able to endure tragedy and setbacks. We’ve got to love what we do and all that it entails, good and bad. We have to learn to find joy in every single thing that happens.

We don’t get to choose what happens to us, but we can always choose how we feel about it.

That is not to say that the good will always outweigh the bad. Or that it comes free and without cost. But there is always some good—even if only barely perceptible at first—contained within the bad.

People are getting a little desperate. People might not show their best elements to you. You must never lower yourself to being a person you don’t like.

the powers of perception, action, and the will.

First, see clearly. Next, act correctly. Finally, endure and accept the world as it is.

Perceive things as they are, leave no option unexplored, then stand strong and transform whatever can’t be changed.

Our actions give us the confidence to ignore or control our perceptions. We prove and support our will with our actions.

“transforms fear into prudence, pain into information, mistakes into initiation and desire into undertaking.”