The Obstacle Is the Way by Ryan Holiday

INTRODUCTION

Overcoming obstacles is a discipline of three critical steps.

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.

It’s three interdependent, interconnected, and fluidly contingent disciplines: Perception, Action, and the Will.

Perception

WHAT IS PERCEPTION? It’s how we see and understand what occurs around us — and what we decide those events will mean. Our perceptions can be a source of strength or of great weakness.

You will come across obstacles in life — fair and unfair. And you will discover, time and time again, that 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. You will learn that this reaction determines how successful we will be in overcoming — or possibly thriving because of — them.

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

We decide what we will make of each and every situation. We decide whether we’ll break or whether we’ll resist. We decide whether we’ll assent or reject. No one can force us to give up or to believe something that is untrue (such as, that a situation is absolutely hopeless or impossible to improve). Our perceptions are the thing that we’re in complete control of.

Just because your mind tells you that something is awful or evil or unplanned or otherwise negative doesn’t mean you have to agree. Just because other people say that something is hopeless or crazy or broken to pieces doesn’t mean it is. We decide what story to tell ourselves. Or whether we will tell one at all.

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. No one said it would be easy and, of course, the stakes are high, but the path is there for those ready to take it.

The more skilled you become seeing things for what they are, the more perception will work for you rather than against you.

How we interpret the events in our lives, our perspective, is the framework for our forthcoming response — whether there will even be one or whether we’ll just lie there and take it.

Focusing exclusively on what is in our power magnifies and enhances our power. But every ounce of energy directed at things we can’t actually influence is wasted — self-indulgent and self-destructive. So much power — ours, and other people’s — is frittered away in this manner.

An entrepreneur is someone with faith in their ability to make something where there was nothing before. To them, the idea that no one has ever done this or that is a good thing. When given an unfair task, some rightly see it as a chance to test what they’re made of — to give it all they’ve got, knowing full well how difficult it will be to win. They see it as an opportunity because it is often in that desperate nothing-to-lose state that we are our most creative.

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.

The demand on you is this: Once you see the world as it is, for what it is, you must act. The proper perception — objective, rational, ambitious, clean — isolates the obstacle and exposes it for what it is.

Action

WHAT IS ACTION? Action is commonplace, right action is not. As a discipline, it’s not any kind of action that will do, but directed action. Everything must be done in the service of the whole. Step by step, action by action, we’ll dismantle the obstacles in front of us. With persistence and flexibility, we’ll act in the best interest of our goals. Action requires courage, not brashness — creative application and not brute force. Our movements and decisions define us: We must be sure to act with deliberation, boldness, and persistence. Those are the attributes of right and effective action. Nothing else — not thinking or evasion or aid from others. Action is the solution and the cure to our predicaments.

No one is coming to save you. And if we’d like to go where we claim we want to go — to accomplish what we claim are our goals — there is only one way. And that’s to meet our problems with the right action.

Therefore, we can always (and only) greet our obstacles

• with energy
• with persistence
• with a coherent and deliberate process
• with iteration and resilience
• with pragmatism
• with strategic vision
• with craftiness and savvy and an eye for opportunity and pivotal moments

While you’re sleeping, traveling, attending meetings, or messing around online, the same thing is happening to you. You’re going soft. You’re not aggressive enough. You’re not pressing ahead. You’ve got a million reasons why you can’t move at a faster pace. This all makes the obstacles in your life loom very large.

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.

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.

If we’re to overcome our obstacles, this is the message to broadcast — internally and externally. We will not be stopped by failure, we will not be rushed or distracted by external noise. We will chisel and peg away at the obstacle until it is gone. Resistance is futile.

Once you start attacking an obstacle, quitting is not an option. It cannot enter your head. Abandoning one path for another that might be more promising? Sure, but that’s a far cry from giving up. Once you can envision yourself quitting altogether, you might as well ring the bell. It’s done.

Consider this mind-set.

• never in a hurry
• never worried
• never desperate
• never stopping short

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

Doing new things invariably means obstacles. A new path is, by definition, uncleared. Only with persistence and time can we cut away debris and remove impediments. Only in struggling with the impediments that made others quit can we find ourselves on untrodden territory — only by persisting and resisting can we learn what others were too impatient to be taught.

On the path to successful action, we will fail — possibly many times. And that’s okay. It can be a good thing, even. 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.

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

It says: Okay, you’ve got to do something very difficult. Don’t focus on that. Instead break it down into pieces. Simply do what you need to do right now. And do it well. And then move on to the next thing. Follow the process and not the prize.

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

Wherever we are, whatever we’re doing and wherever we are going, we owe it to ourselves, to our art, to the world to do it well. That’s our primary duty. And our obligation. When action is our priority, vanity falls away.

In every situation, life is asking us a question, and our actions are the answer. Our job is simply to answer well.

Right action — unselfish, dedicated, masterful, creative — that is the answer to that question. That’s one way to find the meaning of life. And how to turn every obstacle into an opportunity.

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.

Under this kind of force, obstacles break apart. They have no choice. Since you’re going around them or making them irrelevant, there is nothing for them to resist.

If we’re starting from scratch and the established players have had time to build up their defenses, there is just no way we are going to beat them on their strengths. So it’s smarter to not even try, but instead focus our limited resources elsewhere.

The way that works isn’t always the most impressive. Sometimes it even feels like you’re taking a shortcut or fighting unfairly. There’s a lot of pressure to try to match people move for move, as if sticking with what works for you is somehow cheating. Let me save you the guilt and self-flagellation: It’s not.

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 spin our tires in the snow or mud and dig a deeper rut — one that we’ll never get out of.

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

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.

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.

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.

Will

WHAT IS WILL? Will is our internal power, which can never be affected by the outside world. It is our final trump card. If action is what we do when we still have some agency over our situation, the will is what we depend on when agency has all but disappeared.

Will is fortitude and wisdom — not just about specific obstacles but about life itself and where the obstacles we are facing fit within it. It gives us ultimate strength. As in: the strength to endure, contextualize, and derive meaning from the obstacles we cannot simply overcome (which, as it happens, is the way of flipping the unflippable).

These lessons come harder but are, in the end, the most critical to wresting advantage from adversity. In every situation, we can

• Always prepare ourselves for more difficult times.
• Always accept what we’re unable to change.
• Always manage our expectations.
• Always persevere.
• Always learn to love our fate and what happens to us.
• Always protect our inner self, retreat into ourselves.
• Always submit to a greater, larger cause.
• Always remind ourselves of our own mortality.
• And, of course, prepare to start the cycle once more.

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

To be great at something takes practice. Obstacles and adversity are no different. 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.

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.

The only guarantee, ever, is that things will go wrong. The only thing we can use to mitigate this is anticipation. Because the only variable we control completely is ourselves.

Common wisdom provides us with the maxims:

• Beware the calm before the storm.
• Hope for the best, prepare for the worst.
• The worst is yet to come.
• It gets worse before it gets better.

With anticipation, we have time to raise defenses, or even avoid them entirely. We’re ready to be driven off course because we’ve plotted a way back. We can resist going to pieces if things didn’t go as planned. With anticipation, we can endure.

Your obstacle may not be so serious or violent. But they are nevertheless significant and outside your control. They warrant only one response: a smile.

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.

Life is not about one obstacle, but many. What’s required of us is not some shortsighted focus on a single facet of a problem, but simply a determination that we will get to where we need to go, somehow, someway, and nothing will stop us.

Sometimes when we are personally stuck with some intractable or 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? Take it for granted, for a second, that there is nothing else in it for us, nothing we can do for ourselves. How can we use this situation to benefit others? How can we salvage some good out of this? If not for me, then for my family or the others I’m leading or those who might later find themselves in a similar situation.

Help your fellow humans thrive and survive, contribute your little bit to the universe before it swallows you up, and be happy with that. Lend a hand to others. Be strong for them, and it will make you stronger.

Remember the serenity prayer: If something is in our control, it’s worth every ounce of our efforts and energy. Death is not one of those things — it is not in our control how long we will live or what will come and take us from life.

But thinking about and being aware of our mortality creates real perspective and urgency. It doesn’t need to be depressing. Because it’s invigorating.

Reminding ourselves each day that we will die helps us treat our time as a gift. Someone on a deadline doesn’t indulge himself with attempts at the impossible, he doesn’t waste time complaining about how he’d like things to be.

They figure out what they need to do and do it, fitting in as much as possible before the clock expires. They figure out how, when that moment strikes, to say, Of course, I would have liked to last a little longer, but I made a lot of out what I was already given so this works too.

Passing one obstacle simply says you’re worthy of more. The world seems to keep throwing them at you once it knows you can take it. Which is good, because we get better with every attempt.

Perceive things as they are, leave no option unexplored, then stand strong and transform whatever can’t be changed. And they all feed into one another: Our actions give us the confidence to ignore or control our perceptions. We prove and support our will with our actions.

The essence of philosophy is action — in making good on the ability to turn the obstacle upside down with our minds. Understanding our problems for what’s within them and their greater context. To see things philosophically and act accordingly.