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The Obstacle Is The Way Book Summary

Table of Contents

Book Title: The Obstacle Is The Way: The Timeless Art Of Turning Trials into Triumph
Author: Ryan Holiday
Date of Reading: December 2017
Rating: 10/10


What Is The Book About As A Whole:


The Obstacle Is The Way is a book on stoicism that doesn’t want to rewrite the ancient texts; the book shares the ancient wisdom needed to deal with something that’s urgent for every single one of us— overcoming obstacles in any shape or form. 


What Is Being Said In Detail:


The Obstacle Is The Way, just like any of Ryan Holiday’s books, is composed of a three-part structure. 

The first part covers Perception. 

Here, the author provides points, history data, examples, of how to change, control, and recognize the power of your perception. How to look at things that happen with two eyes– the perceiving and observing eye. The observing eye sees what has happened. The perceiving eye sees much more– the thing that happened and what it meant. And that meaning is what can either help you (give you strength) or plunge you into depths of negativity. So discipline your perception and become aware of its power. 

The second part covers Action.

Here, the author provides us with examples on how to practice persistence and iterate your action-taking process to do the job right. Perception is the first step, but that perception comes to fruition only in action. And that action needs to be controlled, smart, and effective to be the right one

The third part covers Will.

This part covers the points of building your inner citadel, anticipating all the negative that can happen so you’re not taken by surprise by them, and finding something bigger than yourself so you can stand up for it. That becomes the true source of your eternal will and fuels your persistence. 


Most Important Keywords, Sentences, Quotes:


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

“Bad companies are destroyed by crisis. Good companies survive them. Great companies are improved by them.”

It’s simple. Simple but, of course, not easy.

We’re soft, entitled, and scared of conflict. Great times are great softeners. Abundance can be its own obstacle, as many people can attest.

While others are excited or afraid, we will remain calm and imperturbable. We will see things simply and straightforwardly, as they truly are—neither good nor bad. This will be an incredible advantage for us in the fight against obstacles.

Where one person sees a crisis, another can see opportunity. Where one is blinded by success, another sees reality with ruthless objectivity. Where one loses control of emotions, another can remain calm. Desperation, despair, fear, powerlessness—these reactions are functions of our perceptions. You must realize: Nothing makes us feel this way; we choose to give in to such feelings. 

Looking the warden in the eye, Carter proceeded to inform him and the guards that he was not giving up the last thing he controlled: himself. In his remarkable declaration, he told them, in so many words, “I know you had nothing to do with the injustice that brought me to this jail, so I’m willing to stay here until I get out. But I will not, under any circumstances, be treated like a prisoner—because I am not and never will be powerless.”

It took nineteen years and two trials to overturn that verdict, but when Carter walked out of prison, he simply resumed his life. No civil suit to recover damages, Carter did not even request an apology from the court. Because to him, that would imply that they’d taken something of his that Carter felt he was owed. That had never been his view, even in the dark depths of solitary confinement. He had made his choice: This can’t harm me—I might not have wanted it to happen, but I decide how it will affect me. No one else has the right.

Ryan Holiday Quote


As for us, we face things that are not nearly as intimidating, and then we promptly decide we’re screwed. This is how obstacles become obstacles.

A mistake becomes training.

Uncertainty and fear are relieved by authority. Training is authority. It’s a release valve. With enough exposure, you can adapt out those perfectly ordinary, even innate, fears that are bred mostly from unfamiliarity. Fortunately, unfamiliarity is simple to fix (again, not easy), which makes it possible to increase our tolerance for stress and uncertainty.

The Greeks had a word for this: apatheia. It’s the kind of calm equanimity that comes with the absence of irrational or extreme emotions.

Does what happened keep you from acting with justice, generosity, self-control, sanity, prudence, honesty, humility, straightforwardness? Nope. Then get back to work!

The phrase “This happened and it is bad” is actually two impressions. The first—“This happened”— is objective. The second—“it is bad”—is subjective.

Musashi understood that the observing eye sees simply what is there. The perceiving eye sees more than what is there. The observing eye sees events, clear of distractions, exaggerations, and misperceptions. The perceiving eye sees “insurmountable obstacles” or “major setbacks” or even just “issues.” It brings its own issues to the fight. The former is helpful, the latter is not.

In its own way, the most harmful dragon we chase is the one that makes us think we can change things that are simply not ours to change. That someone decided not to fund your company, this isn’t up to you. But the decision to refine and improve your pitch? That is. That someone stole your idea or got to it first? No. To pivot, improve it, or fight for what’s yours? Yes.

In fact, half the companies in the Fortune 500 were started during a bear market or recession. Half.

Blessings and burdens are not mutually exclusive. It’s a lot more complicated. Socrates had a mean, nagging wife; he always said that being married to her was good practice for philosophy.

Psychologists call it adversarial growth and post-traumatic growth. “That which doesn’t kill me makes me stronger” is not a cliché but fact.

We’ve all done it. Said: “I am so [overwhelmed, tired, stressed, busy, blocked, outmatched].” And then what do we do about it? Go out and party. Or treat ourselves. Or sleep in. Or wait. It feels better to ignore or pretend. But you know deep down that that isn’t going to truly make it any better. You’ve got to act. And you’ve got to start now.

And that means changing the relationship with failure. It means iterating, failing, and improving. Our capacity to try, try, try is inextricably linked with our ability and tolerance to fail, fail, fail.

It’s time you understand that the world is telling you something with each and every failure and action. It’s feedback—giving you precise instructions on how to improve, it’s trying to wake you up from your cluelessness. It’s trying to teach you something. Listen. Lessons come hard only if you’re deaf to them. Don’t be.

We are A-to-Z thinkers, fretting about A, obsessing over Z, yet forgetting all about B through Y.

Only self-absorbed assholes think they are too good for whatever their current station requires.

You’ve got your mission, whatever it is. To accomplish it, like the rest of us you’re in the pinch between the way you wish things were and the way they actually are (which always seem to be a disaster). How far are you willing to go? What are you willing to do about it? 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?

As Deng Xiaoping once said, “I don’t care if the cat is black or white, so long as it catches mice.” The Stoics had their own reminder: “Don’t go expecting Plato’s Republic.”

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.

The great philosopher Sřren Kierkegaard rarely sought to convince people directly from a position of authority. Instead of lecturing, he practiced a method he called “indirect communication.” Kierkegaard would write under pseudonyms, where each fake personality would embody a different platform or perspective—writing multiple times on the same subject from multiple angles to convey his point emotionally and dramatically. He would rarely tell the reader “do this” or “think that.” Instead he would show new ways of looking at or understanding the world.

Believe it or not, this is the hard way. That’s why it works. Remember, sometimes the longest way around is the shortest way home.

Let two jousting egos sort themselves out instead of jumping immediately into the fray. Sometimes a problem needs less of you—fewer people period—and not more.

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, unlike our disposition, become stronger and better when loose and bold. While others obsess with observing the rules, we’re subtly undermining them and subverting them to our advantage. 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. (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? That is powerful. It’s a power that drives our opponents and competitors nuts. They think we’re toying with them. It’s maddening—like we aren’t even trying, like we’ve tuned out the world. Like we’re immune to external stressors and limitations on the march toward our goals. Because we are.

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.

Problems, as Duke Ellington once said, are a chance for us to do our best. Just our best, that’s it. Not the impossible. We must be willing to roll the dice and lose. Prepare, at the end of the day, for none of it to work.
Anyone in pursuit of a goal comes face-to-face with this time and time again. Sometimes, no amount of planning, no amount of thinking—no matter how hard we try or patiently we persist—will change the fact that some things just aren’t going to work. The world could use fewer martyrs.

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.

Certain things in life will cut you open like a knife. When that happens—at that exposing moment—the world gets a glimpse of what’s truly inside you. So what will be revealed when you’re sliced open by tension and pressure? Iron? Or air? Or bullshit?

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

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.

Your world is ruled by external factors. Promises aren’t kept. You don’t always get what is rightfully yours, even if you earned it. Not everything is as clean and straightforward as the games they play in business school. Be prepared for this.

Let’s be clear, that is not the same thing as giving up. This has nothing to do with action—this is for the things that are immune to action. 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. It takes a real man or woman to face necessity.

If persistence is attempting to solve some difficult problem with dogged determination and hammering until the break occurs, then plenty of people can be said to be persistent. But perseverance is something larger. It’s the long game. It’s about what happens not just in round one but in round two and every round after—and then the fight after that and the fight after that, until the end.

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

As Emerson wrote in 1841: 
If our young men miscarry in their first enterprises, they lose all heart. If the young merchant fails, men say he is ruined. If the finest genius studies at one of our colleges, and is not installed in an office within one year afterwards in the cities or suburbs of Boston or New York, it seems to his friends and to himself that he is right in being disheartened, and in complaining the rest of his life.

As the Haitian proverb puts it: Behind mountains are more mountains.

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

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Book Review (Personal Opinion):


This is one of those classics that you should read, no matter where you are in life. If you’re a student, you will benefit from every lesson of perseverance, framing, will, and emotional constraint in here through your entire life. If you’re older, you will realize that you can still change, adapt, and overcome your life’s obstacles and come out victorious. The Obstacle Is The Way is a phenomenal book and I recommend it to everyone.


Rating: 10/10


This Book Is For (Recommend):

  • A 15-year-old high-schooler who wants to learn how to deal with life’s challenges
  • A 25-year-old graduate that just got hit with “real-life” problems and needs to learn how to cope
  • A 45-year-old sports trainer who wants to instill discipline, solution-orientation, and work-ethic into his team

If You Want To Learn More


Here’s Ryan Holiday holding a speech at Google about Stoicism. 
Ryan Holiday talks at Google


How I’ve Implemented The Ideas From The Book


There are so many ideas I implemented from this book. From the reframing concepts about my (dangerous) travels, to the idea of building an inner citadel so you can fall back to something when times get rough.  However, the main thing I did was the main idea of the book itself– The Obstacle Is The Way. Everything, from my website in my native language to my freelance content marketing business and even to Growthabit is a testament to the idea that obstacle really is the way. And if you follow it, no matter how daunting it looks like, you will lead a good life. 


One Small Actionable Step You Can Do


A journey of 10,000 miles begins with a single step. So decide today to look at your “obstacle,” face it, and decide to walk down that path. It will be the best decision you ever made in your life. 

It’s a small step, followed by another small step, followed by another small step…it’s small, actionable steps all the way to the end.