The Obstacle Is the Way

date Aug 16, 2018
authors Ryan Holiday
reading time 22 mins

Marcus Aurelius’ Meditations

Not to an audience or for publication but to himself, for himself. And what he wrote is undoubtedly one of history’s most effective formulas for overcoming every negative situation we may encounter in life. A formula for thriving not just in spite of whatever happens but because of it.

Our mind

It is more than enough for us. 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. And then he concluded with powerful words destined for maxim. The impediment to action advances action. What stands in the way becomes the way.

Expect setbacks

So that setbacks or problems are always expected and never permanent. Making certain that what impedes us can empower us.

Obstacles as a way to practice virtues

And from what we know, he truly saw each and every one of these obstacles as an opportunity to practice some virtue: patience, courage, humility, resourcefulness, reason, justice, and creativity.

Obstacle brings us choice: blocked or advance?

We are the rightful heirs to this tradition. It’s our birthright. Whatever we face, we have a choice: Will we be blocked by obstacles, or will we advance through and over them?

Blockages are systemic or individual

What blocks us is clear. Systemic: decaying institutions, rising unemployment, skyrocketing costs of education, and technological disruption. Individual: too short, too old, too scared, too poor, too stressed, no access, no backers, no confidence.

Difference among bad, good and great. iPhone was launched in 2007, before the financial crisis!

Subjected to those pressures, these individuals were transformed. They were transformed along the lines that Andy Grove, former CEO of Intel, outlined when he described what happens to businesses in tumultuous times: “Bad companies are destroyed by crisis. Good companies survive them. Great companies are improved by them.

3 types of obstacles

help you accomplish the very specific and increasingly urgent goal we all share: overcoming obstacles. Mental obstacles. Physical obstacles. Emotional obstacles. Perceived obstacles.

Obstacles as emotions

Instead of opposing enemies, we have internal tension. We have professional frustration. We have unmet expectations. We have learned helplessness. And we still have the same overwhelming emotions humans have always had: grief, pain, loss.


It’s three interdependent, interconnected, and fluidly contingent disciplines: Perception, Action, and the Will. It’s a simple process (but again, never easy).

Perception as a weakness

Our perceptions can be a source of strength or of great weakness. If we are emotional, subjective and shortsighted, we only add to our troubles. To prevent becoming overwhelmed by the world around us, we must, as the ancients practiced, learn how to limit our passions and their control over our lives.

Temptation or excitement of the situation

It was this intense self-discipline and objectivity that allowed Rockefeller to seize advantage from obstacle after obstacle in his life, during the Civil War, and the panics of 1873, 1907, and 1929. As he once put it: He was inclined to see the opportunity in every disaster. To that we could add: He had the strength to resist temptation or excitement, no matter how seductive, no matter the situation.

Rockefeller, Buffett and investment

He would make much of his fortune during these market fluctuations—because he could see while others could not. This insight lives on today in Warren Buffet’s famous adage to “be fearful when others are greedy and greedy when others are fearful.” Rockefeller, like all great investors, could resist impulse in favor of cold, hard common sense.

How do we react to obstacles?

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.

Objective control

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

Our mind is intact with us

They can throw us in jail, label us, deprive us of our possessions, but they’ll never control our thoughts, our beliefs, our reactions. Which is to say, we are never completely powerless. Even in prison, deprived of nearly everything, some freedoms remain. Your mind remains your own (if you’re lucky, you have books) and you have time—lots of time.

Even in prison…

Many great figures, from Nelson Mandela to Malcolm X, have come to understand this fundamental distinction. It’s how they turned prison into the workshop where they transformed themselves and the schoolhouse where they began to transform others.

Creation and destruction of obstacles are in our mind

other words, through our perception of events, we are complicit in the creation—as well as the destruction—of every one of our obstacles. 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.

There is always a way through

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.

Train your mind first

When America raced to send the first men into space, they trained the astronauts in one skill more than in any other: the art of not panicking. When people panic, they make mistakes. They override systems. They disregard procedures, ignore rules. They deviate from the plan. They become unresponsive and stop thinking clearly. They just react—not to what they need to react to, but to the survival hormones that are coursing through their veins.

How the astronauts were trained

Slowly, in a graded series of “exposures,” the astronauts were introduced to every sight and sound of the experience of their firing into space. They did it so many times that it became as natural and familiar as breathing. They’d practice all the way through, holding nothing back but the liftoff itself, making sure to solve for every variable and remove all uncertainty.


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.

Emotions and nagativity

It’s the kind of calm equanimity that comes with the absence of irrational or extreme emotions. Not the loss of feeling altogether, just the loss of the harmful, unhelpful kind. Don’t let the negativity in, don’t let those emotions even get started. Just say: No, thank you. I can’t afford to panic.

Objective and subjective part of every event

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.

Observing (objective) and perceiving (subjective)

In The Book of Five Rings, he notes the difference between observing and perceiving. The perceiving eye is weak, he wrote; the observing eye is strong. Musashi understood that the observing eye sees simply what is there. The perceiving eye sees more than what is there.

When someone makes you feel intimidated

Epictetus told his students, when they’d quote some great thinker, to picture themselves observing the person having sex. It’s funny, you should try it the next time someone intimidates you or makes you feel insecure. See them in your mind, grunting, groaning, and awkward in their private life—just like the rest of us.

Perspective = Context + Framing

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 and action

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

Serenity Prayer

God, grant me the serenity to accept the things I cannot change The courage to change the things I can, And the wisdom to know the difference.

What are directly under our control?

And 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.

Focus on what we can control

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.

Many businesses were created during financial crisis

For the most part, these businesses had little awareness they were in some historically significant depression. Why? Because the founders were too busy existing in the present — actually dealing with the situation at hand. They didn’t know whether it would get better or worse, they just knew what was. They had a job they wanted to do, a great idea they believed in or a product they thought they could sell. They knew they had payroll to meet.

Wasted energy

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.

Implications of our obstacles

The implications of our obstacle are theoretical—they exist in the past and the future. We live in the moment. And the more we embrace that, the easier the obstacle will be to face and move.

Steadiness in decision

It’s one thing to not be overwhelmed by obstacles, or discouraged or upset by them. This is something that few are able to do. But after you have controlled your emotions, and you can see objectively and stand steadily, the next step becomes possible: a mental flip, so you’re looking not at the obstacle but at the opportunity within it.

Sports and injury

Sports psychologists recently did a study of elite athletes who were struck with some adversity or serious injury. Initially, each reported feeling isolation, emotional disruption, and doubts about their athletic ability. Yet afterward, each reported gaining a desire to help others, additional perspective, and realization of their own strengths. In other words, every fear and doubt they felt during the injury turned into greater abilities in those exact areas.

What doesn’t kill me…

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

Losing your head in the event

It’s a huge step forward to realize that the worst thing to happen is never the event, but the event and losing your head. Because then you’ll have two problems (one of them unnecessary and post hoc).

Deconstructing the obstacle

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.

Vent and then get back to work!

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. Because you have to get back to work. Because each obstacle we overcome makes us stronger for the next one.

Move always

Be deliberate, of course, but you always need to be moving forward. And that’s the final part: Stay moving, always.

Chisel away bit by bit

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.


In 1878, Thomas Edison wasn’t the only person experimenting with incandescent lights. But he was the only man willing to test six thousand different filaments — including one made from the beard hair of one of his men—inching closer each time to the one that would finally work. And, of course, he eventually found it—proving that genius often really is just persistence in disguise.

Slow process

Too many people think that great victories like Grant’s and Edison’s came from a flash of insight. That they cracked the problem with pure genius. In fact, it was the slow pressure, repeated from many different angles, the elimination of so many other more promising options, that slowly and surely churned the solution to the top of the pile.


For most of what we attempt in life, chops are not the issue. We’re usually skilled and knowledgeable and capable enough. But do we have the patience to refine our idea? The energy to beat on enough doors until we find investors or supporters? The persistence to slog through the politics and drama of working with a group?

Persist and Resist

Remember and remind yourself of a phrase favored by Epictetus: “persist and resist.” Persist in your efforts. Resist giving in to distraction, discouragement, or disorder.

Difficulties will always keep coming

Edison once explained that in inventing, “the first step is an intuition—and comes with a burst—then difficulties arise.” What set Edison apart from other inventors is tolerance for these difficulties, and the steady dedication with which he applied himself toward solving them.

Energy is renewable

In other words: It’s supposed to be hard. Your first attempts aren’t going to work. It’s going to take a lot out of you—but energy is an asset we can always find more of. It’s a renewable resource. Stop looking for an epiphany, and start looking for weak points.


The point is to immediately see how customers respond. And, if that response is poor, to be able to fail cheaply and quickly. To avoid making or investing in a product customers do not want.

The task at hand

Think about what you needed to do in this drill, on this play, in this moment. That’s the process: Let’s think about what we can do today, the task at hand.”

Break it down. Focus on the process

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 finishing. Finishing games. Finishing workouts. Finishing film sessions. Finishing drives. Finishing reps. Finishing plays. Finishing blocks. Finishing the smallest task you have right in front of you and finishing it well.

Order and process

The unordered mind loses track of what’s in front of it—what matters—and gets distracted by thoughts of the future. The process is order, it keeps our perceptions in check and our actions in sync.

Ship what you can first

The first iPhone was revolutionary, but it still shipped without a copy-and-paste feature or a handful of other features Apple would have liked to have included. Steve Jobs, the supposed perfectionist, knew that at some point, you have to compromise. What mattered was that you got it done and it worked.

Radical pragmatist

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

Focus on the process

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.

Free in the mind

He was able to do this because he was free. He was free where it mattered: inside.

Will vs strength

Too often people think that will is how bad we want something. In actuality, the will has a lot more to do with surrender than with strength.

True will is silent

True will is quiet humility, resilience, and flexibility; the other kind of will is weakness disguised by bluster and ambition. See which lasts longer under the hardest of obstacles.

Lincoln and dealing with depression

Lincoln’s personal challenges had been so intense that he came to believe they were destined for him in some way, and that the depression, especially, was a unique experience that prepared him for greater things. He learned to endure all this, articulate it, and find benefit and meaning from it. Understanding this is key to understanding the man’s greatness.

This too shall pass

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

Terrible is taking the path of least resistance

The path of least resistance is a terrible teacher. We can’t afford to shy away from the things that intimidate us. We don’t need to take our weaknesses for granted.


Are you okay being alone? Are you strong enough to go a few more rounds if it comes to that? Are you comfortable with challenges? Does uncertainty bother you? How does pressure feel?

Conducting a premortem

A premortem is different. In it, 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.

Prepare for the worse

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.

Strength to bear the worse

But the person who has rehearsed in their mind what could go wrong will not be caught by surprise. The person ready to be disappointed won’t be. They will have the strength to bear it. They are not as likely to get discouraged or to shirk from the task that lies before them, or make a mistake in the face of it.

Imagination vs Reality

You know what’s better than building things up in your imagination? Building things up in real life. Of course, it’s a lot more fun to build things up in your imagination than it is to tear them down. But what purpose does that serve?


It doesn’t always feel that way but 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.

Fate? What will happen, will happen?

It’s time to be humble and flexible enough to acknowledge the same in our own lives. That there is always someone or something that could change the plan. And that person is not us. As the saying goes, “Man proposes but God disposes.” As fate would have it. Heaven forbid. Nature permitting. Murphy’s Law.


Learning not to kick and scream about matters we can’t control is one thing. Indifference and acceptance are certainly better than disappointment or rage. Very few understand or practice that art.

Collapse of will

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

Whine and complain

We whine and complain and mope when things won’t go our way. We’re crushed when what we were “promised” is revoked—as if that’s not allowed to happen. Instead of doing much about it, we sit at home and play video games or travel or worse, pay for more school with more loan debt that will never be forgiven. And then we wonder why it isn’t getting any better.

Making it all personal

Stop making it harder on yourself by thinking about I, I, I. 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 personally, no wonder you feel so alone. You’ve inflated your own role and importance.

We are all subject to events

When really, there is a world beyond our own personal experience filled with people who have dealt with worse. We’re not special or unique simply by virtue of being. We’re all, at varying points in our lives, the subject of random and often incomprehensible events.

Near-death experience

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. And so it was for Montaigne. Coming so close to death energized him, made him curious. No longer was death something to be afraid of—looking it in the eyes had been a relief, even inspiring.

Death as a motivation

It means that embracing the precariousness of our own existence can be exhilarating and empowering. Our fear of death is a looming obstacle in our lives. It shapes our decisions, our outlook, and our actions.


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.

Momento Mori

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.

If you are building bigger things, then there are always obstacles

As the Haitian proverb puts it: Behind mountains are more mountains. Elysium is a myth. One does not overcome an obstacle to enter the land of no obstacles. On the contrary, the more you accomplish, the more things will stand in your way. There are always more obstacles, bigger challenges. You’re always fighting uphill. Get used to it and train accordingly.


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 philosopher and writer Nassim Nicholas Taleb defined a Stoic as someone who “transforms fear into prudence, pain into information, mistakes into initiation and desire into undertaking.” It’s a loop that becomes easier over time.

Obstacle is the way…

But let’s say it once again just to remind ourselves: 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.