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

By Ryan Holiday


I want to hate Ryan Holiday. He’s younger than me, richer, and more successful. He is also a practitioner of stoicism, and a terrific writer. Those two attributes came together to create this book. Using examples from history–figures include Ulysses S. Grant and Abraham Lincoln–Holiday has produced a sort of how-to guide on the application of Stoic philosophy to modern life. Ever have a book that hits you in just the right way, at exactly the right time? This is mine.

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.
-Marcus Aurelius

This will be a book of ruthless pragmatism and stories from history that illustrate the arts of relentless persistence and indefatigable ingenuity. It teaches you how to get unstuck, unfucked, and unleashed.

“The Things which hurt,” Benjamin Franklin wrote, “instruct.”

It begins with how we look at our specific problems, our attitude or approach; then the energy and creativity with which we actively break them down and turn them into opportunities; finally, the cultivation and maintenance of an inner will that allows us to handle defeat and difficulty.

“I shall never cease to be grateful for the three and a half years of apprenticeship and the difficulties to be overcome, all along the way.” -John D. Rockefeller

There are a few things to keep in mind when faced with a seemingly insurmountable obstacle. We must try:

  • To be objective
  • To control emotions and keep an even keel
  • To choose to see the good in a situation
  • To steady our nerves
  • To ignore what disturbs or limits others
  • To place things in perspective
  • To revert to the present moment
  • To focus on what can be controlled

This can’t harm me–I might not have wanted it to happen, but I decide how it will affect me.

When we aim high, pressure and stress obligingly come along for the ride. Stuff is going to happen that catches us off guard, threatens or scares us. Surprises (unpleasant ones, mostly) are almost guaranteed. The risk of being overwhelmed is always there.
In these situations, talent is not the most sought-after characteristic. Grace and poise are, because those two attributes precede the opportunity to deploy any other skill.

Defiance and acceptance come together well in the following principle: There is always a countermove, always an escape or a way through, so there is no reason to get worked up.

Training is authority. It’s a release valve. With enough exposure, you can adapt out those perfectly ordinary, even innate, fears that are bred from unfamiliarity.

“Does what happened keep you from acting with justice, generosity, self-control, sanity, prudence, honesty, humility, straightforwardness?” -Marcus Aurelius

Take your situation and pretend it is not happening to you. Pretend it is not important, that it doesn’t matter. How much easier would it be for you to know what to do?

Perspective has two definitions.
1. Context: a sense of the larger picture of the world, not just what is immediately in front of us
2. Framing: an individual’s unique way of looking at the world, a way that interprets its events

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

Behind the Serenity Prayer is a two-thousand-year-old Stoic phrase: “What is up to us, what is not up to us.”

In its own way, the most harmful dragon we can chase is the one that makes us think we can change things that are simply not ours to change.

Our problem is that we’re always trying to find out what things mean–why things are the way they are. As though the why matters. Emerson put it best: “We cannot spend the day in explanation.” Don’t waste time on false constructs.

Catch your mind when it wanders–don’t let it get away from you. Discard distracting thoughts. Leave things well enough alone–no matter how much you feel like doing otherwise.

If you mean it when you say you’re at the end of your rope and would rather quit, you actually have a unique chance to grow and improve yourself. A unique opportunity to experiment with different solutions, to try different tactics, or to take on new projects to add to your skill set.

“That which doesn’t kill me makes me stronger,” is not a cliche but fact.

When people are:
rude or disrespectful, they underestimate us. A huge advantage.
conniving, we won’t have to apologize when we make an example out of them.
critical or question our abilities, lower expectations are easier to exceed.
lazy, makes whatever we accomplish seem all the more admirable.

Problems are rarely as bad as we think–or rather, they are precisely as bad as we think.

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. And the only way you’ll do something spectacular is by using it all to your advantage.

No one is saying you can’t take a minute to think, Dammit, this sucks. By all means, vent. Exhale. Take stock. Just don’t take too long.

We delay when we should initiate. We jog when we should be running or, better yet, sprinting. And then we’re shocked–shocked!–when nothing big ever happens, when opportunities never show up, when new obstacles begin to pile up, or the enemies finally get their act together.

Just because the conditions aren’t exactly to your liking, or you don’t feel ready yet, doesn’t mean you get a pass.

Stop looking for angels, and start looking for angles.

Action and failure are two sides of the same coin. One doesn’t come without the other. What breaks this critical connection down is when people stop acting–because they’ve taken failure the wrong way.

Like any good school, learning from failure isn’t free. The tuition is paid in discomfort or loss and having to start over.

Being trapped is just a position, not a fate. You get out of it by addressing and eliminating each part of that position through small, deliberate actions–not by trying (and failing) to push it away with superhuman strength.

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

As they say in Brazilian jujitsu, it doesn’t matter how you get your opponents to the ground, after all, only that you take them down.

Don’t think small, but make the distinction between the critical and the extra.

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

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. They choose to exert calculated force where it will be effective, rather than straining and struggling with pointless attrition tactics.

The inertia of success makes it much harder to truly develop good technique. People or companies who have that size advantage never really have to learn the process when they’ve been able to coast on brute force. And that works for them… until it doesn’t.

Opposites work. Nonaction can be action. It uses the power of others and allows us to absorb their power as our own.

We get so consumed with moving forward that we forget that there are other ways to get where we are heading. It doesn’t naturally occur to us that standing still–or in some cases, even going backward–might be the best way to advance. Don’t just do something, stand there!

Think water. When dammed by a man-made obstacle, it does not simply sit stagnant. Instead, its energy is stored and deployed, fueling the power plants that run entire cities.

To be physically and mentally loose takes no talent. That’s just recklessness. To be physically and mentally tight? That’s called anxiety. But physical looseness combined with mental restraint? That’s powerful.

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.

We have it within us to be the type of people who try to get things done, try with everything we’ve got and, whatever verdict comes in, are ready to accept it instantly and move on to whatever is next.

“This too shall pass,” was Lincoln’s favorite saying, one he once said was applicable in any and every situation one could encounter.

Will is fortitude and wisdom–not just about specific obstacles but about life itself and where the obstacles we are facing fit within it.

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

We craft our spiritual strength through physical exercise, and our physical hardiness through mental practice.

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.

The path of least resistance is a terrible teacher.

Your plan and the way things turn out rarely resemble each other. What you think you deserve is also rarely what you’ll get.

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.

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

It is far easier to talk of the way things should be. It takes toughness, humility, and will to accept them for what they actually are.

The next step after we discard our expectations and accept what happens to us, after understanding that certain things–particularly bad things–are outside our control, is this: loving whatever happens to us and facing it with unfailing cheerfulness.

If the event must occur, Amor fati (a love of fate) is the response.

There are far more failures in the world due to a collapse of will than there will ever be from objectively conclusive external events.

Our plans–even our bodies–can be broken. But belief in ourselves? No matter how many times we are thrown back, we alone retain the power to decide to go once more.

“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. There is no better time than now to have a moral and civic backbone. To have a moral and civic true north. This is a tremendous opportunity for you, a young person, to be heroic.” -Henry Rollins

Stop putting that dangerous “I” in front of events. I did this. I was so smart. I had that. I deserve better than this. No wonder you take losses so personally, no wonder you feel so alone. You’ve inflated your own role and importance.

Whatever you’re going through, whatever is holding you down or standing in your way, can be turned into a source of strength–by thinking of people other than yourself.

Stop pretending that what you’re going through is somehow special or unfair. Whatever trouble you’re having–no matter how difficult–is not some unique misfortune picked out especially for you. It just is what it is.

It’s a story as old as time. Man nearly dies, he takes stock, and emerges from the experience a completely different, and better, person.

If even our own mortality can have some benefit, how dare you say that you can’t derive value from each and every other kind of obstacle you encounter?

Passing one obstacle simply says you’re worthy of more.

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

Of course, it is not simply enough to read this or say it. We must practice these maxims rolling them over and over in our minds and acting on them until they become muscle memory.

Philosophy was never what happened in the classroom. It was a set of lessons from the battlefield of life.


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