The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph (Ryan Holiday)


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.

Whatever we face, we have a choice: Will we be blocked by obstacles, or will we advance through and over them?

Every obstacle is unique to each of us. But the responses they elicit are the same: Fear. Frustration. Confusion. Helplessness. Depression. Anger.

I want to show you the way to turn every obstacle into an advantage.

How to turn the many negative situations we encounter in our lives into positive ones

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

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 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.

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 is how you see the opportunity within the obstacle. It does not happen on its own. It is a process — one that results from self-discipline and logic.


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

Our perceptions are the thing that we’re in complete control of.

There is no good or bad without us, there is only perception. There is the event itself and the story we tell ourselves about what it means. That’s a thought that changes everything,


Nerve is a matter of defiance and control.

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.


Obstacles make us emotional, but the only way we’ll survive or overcome them is by keeping those emotions in check — if we can keep steady no matter what happens, no matter how much external events may fluctuate.

If an emotion can’t change the condition or the situation you’re dealing with, it is likely an unhelpful emotion. Or, quite possibly, a destructive one.

Real strength lies in the control or, as Nassim Taleb put it, the domestication of one’s emotions, not in pretending they don’t exist.


Objectivity means removing “you” — the subjective part — from the equation.

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? How much more quickly and dispassionately could you size up the scenario and its options? You could write it off, greet it calmly. Think of all the ways that someone could solve a specific problem. No, really think. Give yourself clarity, not sympathy — there’ll be plenty of time for that later. It’s an exercise, which means it takes repetition. The more you try it, the better you get at it. The more skilled you become seeing things for what they are, the more perception will work for you rather than against you.


Perspective is everything. That is, when you can break apart something, or look at it from some new angle, it loses its power over you. A simple shift in perspective can change our reaction entirely.

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.

Perspective has two definitions:

  • Context: a sense of the larger picture of the world, not just what is immediately in front of us
  • Framing: an individual’s unique way of looking at the world, a way that interprets its events

Perception precedes action. Right action follows the right perspective.


What if you focused on what you can change?

What is up to us? Our emotions Our judgments Our creativity Our attitude Our perspective Our desires Our decisions Our determination This is our playing field, so to speak. Everything there is fair game. What is not up to us? Well, you know, everything else. The weather, the economy, circumstances, other people’s emotions or judgments, trends, disasters, et cetera.

When it comes to perception, this is the crucial distinction to make: the difference between the things that are in our power and the things that aren’t.

Focusing exclusively on what is in our power magnifies and enhances our power.

To see an obstacle as a challenge, to make the best of it anyway, that is also a choice — a choice that is up to us.


In our own lives, we aren’t content to deal with things as they happen. We have to dive endlessly into what everything “means,” whether something is “fair” or not, what’s “behind” this or that, and what everyone else is doing. Then we wonder why we don’t have the energy to actually deal with our problems. Or we get ourselves so worked up and intimidated because of the overthinking, that if we’d just gotten to work we’d probably be done already.

The implications of our obstacle are theoretical — they exist in the past and the future. We live in the moment.

You can take the trouble you’re dealing with and use it as an opportunity to focus on the present moment. To ignore the totality of your situation and learn to be content with what happens, as it happens.


To aim low meant to accept mediocre accomplishment. But a high aim could, if things went right, create something extraordinary.

We shouldn’t listen too closely to what other people say (or to what the voice in our head says, either). We’ll find ourselves erring on the side of accomplishing nothing. Be open. Question.

It’s this all-too-common impulse to complain, defer, and then give up that holds us back. 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. Our best ideas come from there, where obstacles illuminate new


Let’s take a circumstance we’ve all been in: having a bad boss. All we see is the hell. All we see is that thing bearing down on us. We flinch. But what if you regarded it as an opportunity instead of a disaster?

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. You can study this bad boss and learn from him — while you fill out your résumé and hit up contacts for a better job elsewhere. You can prepare yourself for that job by trying new styles of communication or standing up for yourself, all with a perfect safety net for yourself: quitting and getting out of there. With this new attitude and fearlessness, who knows, you might be able to extract concessions and find that you like the job again. One day, the boss will make a mistake, and then you’ll make your move and outmaneuver them. It will feel so much better than the alternative — whining, bad-mouthing, duplicity, spinelessness.

The obstacle is an advantage, not adversity. The enemy is any perception that prevents us from seeing 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.

Boldness is acting anyway, even though you understand the negative and the reality of your obstacle. Decide to tackle what stands in your way — not because you’re a gambler defying the odds but because you’ve calculated them and boldly embraced the risk.

PART II 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.


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


Start. Anywhere. Anyhow.

Don’t care if the conditions are perfect or if they’re being slighted. Because they know that once they get started, if they can just get some momentum, they can make it work.

While you’re sleeping, traveling, attending meetings, or messing around online,

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. For some reason, these days we tend to downplay the importance of aggression, of taking risks, of barreling forward. It’s probably because it’s been negatively associated with certain notions of violence or masculinity.

Stay moving, always.

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 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.

Consider this mind-set. never in a hurry never worried never desperate never stopping short


Failure is a Feature.

Failure really can be an asset if what you’re trying to do is improve, learn, or do something new. It’s the preceding feature of nearly all successes. There’s nothing shameful about being wrong, about changing course. Each time it happens we have new options. Problems become opportunities.

In a world where we increasingly work for ourselves, are responsible for ourselves, it makes sense to view ourselves like a start-up — a start-up of one. That means changing the relationship with failure. It means iterating, failing, and improving.


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 finishing.

The process is the voice that demands we take responsibility and ownership. That prompts us to act even if only in a small way.

Moving forward, one step at a time.

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


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.

There’s nothing shameful about sweeping. It’s just another opportunity to excel — and to learn.

Everything we do matters. Everything is a chance to do and be your best.

To whatever we face, our job is to respond with: hard work honesty helping others as best we can

Respect the craft and make something beautiful.


Focusing on results instead of pretty methods.

Pragmatism is not so much realism as flexibility. There are a lot of ways to get from point A to point B. It doesn’t have to be a straight line. It’s just got to get you where you need to go. Do the best with what you’ve got.

Think progress, not perfection.


Be creative, to find workarounds, to sublimate the ego and do anything to win besides challenging our enemies where they are strongest.

You don’t convince people by challenging their longest and most firmly held opinions. You find common ground and work from there. Or you look for leverage to make them listen. Or you create an alterative with so much support from other people that the opposition voluntarily abandons its views and joins your camp.

Sometimes the longest way around is the shortest way home.


Gandhi’s extensive satyagraha campaign and civil disobedience show that action has many definitions. It’s not always moving forward or even obliquely. It can also be a matter of positions. It can be a matter of taking a stand.

You can use the actions of others against themselves instead of acting yourself.

Opposites work. Nonaction can be action. Instead of fighting obstacles, find a means of making them defeat themselves.


We all have our own constraints to deal with — rules and social norms we’re required to observe that we’d rather not.

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.


“You never want a serious crisis to go to waste. Things that we had postponed for too long, that were long-term, are now immediate and must be dealt with. [A] crisis provides the opportunity for us to do things that you could not do before.”

Life speeds on the bold and favors the brave.


Perceptions can be managed. Actions can be directed.

We can always think clearly, respond creatively. Look for opportunity, seize the initiative. What we can’t do is control the world around us — not as much as we’d like to, anyway. We might perceive things well, then act rightly, and fail anyway.

Nothing can ever prevent us from trying.



Will is our internal power, which can never be affected by the outside world.


If Perception and Action were the disciplines of the mind and the body, then Will is the discipline of the heart and the soul. The will is the one thing we control completely, always.

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

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.


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

The path of least resistance is a terrible teacher. We can’t afford to shy away from the things that intimidate us.


Premortem technique: we look to envision what could go wrong, what will go wrong, in advance, before we start. Far too many ambitious undertakings fail for preventable reasons. Far too many people don’t have a backup plan because they refuse to consider that something might not go exactly as they wish.

Always prepared for disruption, always working that disruption into our plans.

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.

Anticipation doesn’t magically make things easier, of course. But we are prepared for them to be as hard as they need to be, as hard as they actually are.


Constraints in life are a good thing. Especially if we can accept them and let them direct us. They push us to places and to develop skills that we’d otherwise never have pursued.

You don’t have to like something to master it — or to use it to some advantage. When the cause of our problem lies outside of us, we are better for accepting it and moving on. For ceasing to kick and fight against it, and coming to terms with it. The Stoics have a beautiful name for this attitude. They call it the Art of Acquiescence.


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.

We don’t get to choose what happens to us, but we can always choose how we feel about it. And why on earth would you choose to feel anything but good? We can choose to render a good account of ourselves. If the event must occur, Amor fati (a love of fate) is the response.


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.

Persistence is an action. Perseverance is a matter of will. One is energy. The other, endurance. And, of course, they work in conjunction with each other.

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

“with the exercise of self-trust, new powers shall appear.”


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.

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.


Every culture has its own way of teaching the same lesson: Memento mori, the Romans would remind themselves. Remember you are mortal.

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.


The great law of nature is that it never stops. There is no end. Just when you think you’ve successfully navigated one obstacle, another emerges. But that’s what keeps life interesting. And as you’re starting to see, that’s what creates opportunities.

Each time, you’ll learn something. Each time, you’ll develop strength, wisdom, and perspective. Each time, a little more of the competition falls away. Until all that is left is you: the best version of you.

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

FINAL THOUGHTS The Obstacle Becomes the Way

See things for what they are.

Do what we can.

Endure and bear what we must.

What blocked the path now is a path.

What once impeded action advances action.

The Obstacle is the Way.

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