The Obstacle is the Way

The Obstacle is the Way Book Cover The Obstacle is the Way
Ryan Holiday
Business & Economics

The idea of resilience is a recurring theme for me. I might have started seriously reflecting on it while reading “The Obstacle is the Way.” Holliday, Greitens, Pressfield all using the Classics, the ancient philosophers and poets, the great military leaders, the great sports coaches to help us build practices of reflection, deep understanding, persistence, resilience.

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.

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

There have been countless lessons (and books) about achieving success, but no one ever taught us how to overcome failure, how to think about obstacles, how to treat and triumph over them, and so we are stuck. Beset on all sides, many of us are disoriented, reactive, and torn. We have no idea what to do.

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

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

Objective judgment, now at this very moment. Unselfish action, now at this very moment. Willing acceptance—now at this very moment—of all external events. That’s all you need. —MARCUS AURELIUS

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.

But even as a young man, Rockefeller had sangfroid: unflappable coolness under pressure. He could keep his head while he was losing his shirt. Better yet, he kept his head while everyone else lost theirs.

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.

We live in our own Gilded Age. In less than a decade, we’ve experienced two major economic bubbles, entire industries are crumbling, lives have been disrupted. What feels like unfairness abounds. Financial downturns, civil unrest, adversity. People are afraid and discouraged, angry and upset and gathered in Zuccotti Park or in communities online.

Too often we react emotionally, get despondent, and lose our perspective. All that does is turn bad things into really bad things. Unhelpful perceptions can invade our minds—that sacred place of reason, action and will—and throw off our compass.

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. And that logic is available to you. You just need to deploy it.

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.

In 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’s another story about Grant at City Point, Union headquarters, near Richmond. Troops were unloading a steamboat and it suddenly exploded. Everyone hit the dirt except Grant, who was seen running toward the scene of the explosion as debris and shells and even bodies rained down.

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.

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.

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.

As Gavin de Becker writes in The Gift of Fear, “When you worry, ask yourself, ‘What am I choosing to not see right now?’ What important things are you missing because you chose worry over introspection, alertness or wisdom?” Another way of putting it: Does getting upset provide you with more options?

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. So go ahead, feel it. Just don’t lie to yourself by conflating emoting about a problem and dealing with it. Because they are as different as sleeping and waking.

Or try Marcus’s question: Does what happened keep you from acting with justice, generosity, self-control, sanity, prudence, honesty, humility, straightforwardness?

The sixteenth-century Samurai swordsman Miyamoto Musashi won countless fights against feared opponents, even multiple opponents, in which he was swordless. 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. 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.

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. Fear is debilitating, distracting, tiring, and often irrational. Pericles understood this completely, and he was able to use the power of perspective to defeat it.

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

We subconsciously submit to what Seth Godin, author and entrepreneur, refers to as the “tyranny of being picked.”

Focus on the moment, not the monsters that may or may not be up ahead.

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.

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

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.

You know what she said to that offer? She said yes. Because that’s what people who defy the odds do. That’s how people who become great at things—whether it’s flying or blowing through gender stereotypes—do. They start. Anywhere. Anyhow. They 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.

The wind is rising. The bell’s been rung. Get started, get moving.

The German troops had a saying about him: Where Rommel is, there is the front.

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

Like Earhart, Rommel knew from history that those who attack problems and life with the most initiative and energy usually win. He was always pushing ahead, keeping the stampede on the more cautious British forces to devastating effect.

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.

At Vicksburg, Grant learned two things. First, persistence and pertinacity were incredible assets and probably his main assets as a leader. Second, as often is the result from such dedication, in exhausting all the other traditional options, he’d been forced to try something new. That option—cutting loose from his supply trains and living off the spoils of hostile territory—was a previously untested strategy that the North could now use to slowly deplete the South of its resources and will to fight. In persistence, he’d not only broken through: In trying it all the wrong ways, Grant discovered a totally new way—the way that would eventually win the war.

Both unceasing, embodying cool persistence and the spirit of the line from the Alfred Lord Tennyson poem about that other Ulysses, “to strive, to seek, to find.” Both, refusing to give up. Turning over in their minds option after option, and trying each one with equal enthusiasm. Knowing that eventually—inevitably—one will work. Welcoming the opportunity to test and test and test, grateful for the priceless knowledge this reveals.

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

When failure does come, ask: What went wrong here? What can be improved? What am I missing? This helps birth alternative ways of doing what needs to be done, ways that are often much better than what we started with. Failure puts you in corners you have to think your way out of. It is a source of breakthroughs.

In North Africa, the British learned how to fight the Germans—and early on they learned mostly by failure. But that was acceptable, because they’d anticipated a learning curve and planned for it.

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.

Excellence is a matter of steps. Excelling at this one, then that one, and then the one after that.

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.

Everything we do matters—whether it’s making smoothies while you save up money or studying for the bar—even after you already achieved the success you sought. Everything is a chance to do and be your best. Only self-absorbed assholes think they are too good for whatever their current station requires.

Respect the craft and make something beautiful.

Think progress, not perfection.

Washington wasn’t a guerrilla, but he was close enough. He was wily, evasive, often refusing to battle. His army was small, undertrained, undersupplied, and fragile. He waged a war mostly of defense, deliberately avoiding large formations of British troops. For all the rhetoric, most of his maneuvers were pinpricks against a stronger, bigger enemy. Hit and run. Stick and move. Never attack where it is obvious, Washington told his men. Don’t attack as the enemy would expect, he explained, instead, “Where little danger is apprehended, the more the enemy will be unprepared and consequently there is the fairest prospect of success.” He had a powerful sense of which minor skirmishes would feel and look like major victories.

Washington rarely got trapped—he always had a way out.

In a study of some 30 conflicts comprising more than 280 campaigns from ancient to modern history, the brilliant strategist and historian B. H. Liddell Hart came to a stunning conclusion: In only 6 of the 280 campaigns was the decisive victory a result of a direct attack on the enemy’s main army. Only six. That’s 2 percent. If not from pitched battles, where do we find victory? From everywhere else. From the flanks. From the unexpected. From the psychological. From drawing opponents out from their defenses. From the untraditional. From anything but . . . As Hart writes in his masterwork Strategy: [T]he Great Captain will take even the most hazardous indirect approach—if necessary over mountains, deserts or swamps, with only a fraction of the forces, even cutting himself loose from his communications. Facing, in fact, every unfavorable condition rather than accept the risk of stalemate invited by direct approach.

Think of Hall of Fame coach Phil Jackson and his famous triangle offense, which is designed to automatically route the basketball away from defensive pressure rather than attack it directly.

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. Until they meet you and you make quick work of them with deft and oblique maneuvers, when you refuse to face them in the one setting they know: head-to-head.

But we also have to be ready to see that restraint might be the best action for us to take. Sometimes in your life you need to have patience—wait for temporary obstacles to fizzle out. 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.

If you look at history, some of our greatest leaders used shocking or negative events to push through much-needed reforms that otherwise would have had little chance of passing. We can apply that in our own lives.

Every chemical reaction requires a catalyst. Let this be yours.

We sit here and complain that we’re not being given opportunities or chances. But we are.

In the meantime, cling tooth and nail to the following rule: not to give in to adversity, not to trust prosperity, and always take full note of fortune’s habit of behaving just as she pleases. —SENECA

The CEO is forcing an exercise in hindsight—in advance. She is using a technique designed by psychologist Gary Klein known as 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.

Mike Tyson, who, reflecting on the collapse of his fortune and fame, told a reporter, “If you’re not humble, life will visit humbleness upon you.”

But like all great ideas, it is actually nothing new. The credit goes to the Stoics. They even had a better name: premeditatio malorum (premeditation of evils).

Always prepared for disruption, always working that disruption into our plans. Fitted, as they say, for defeat or victory. And let’s be honest, a pleasant surprise is a lot better than an unpleasant one. What if . . . Then I will . . . What if . . . Instead I’ll just . . . What if . . . No problem, we can always . . . And 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. Because sometimes the only answer to “What if . . .” is, It will suck but we’ll be okay.

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.

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.

LOVE EVERYTHING THAT HAPPENS: AMOR FATI My formula for greatness in a human being is amor fati: that one wants nothing to be different, not forward, not backward, not in all eternity. Not merely bear what is necessary, still less conceal it . . . but love it. —NIETZSCHE

At age sixty-seven, Thomas Edison returned home early one evening from another day at the laboratory. Shortly after dinner, a man came rushing into his house with urgent news: A fire had broken out at Edison’s research and production campus a few miles away. Fire engines from eight nearby towns rushed to the scene, but they could not contain the blaze. Fueled by the strange chemicals in the various buildings, green and yellow flames shot up six and seven stories, threatening to destroy the entire empire Edison had spent his life building. Edison calmly but quickly made his way to the fire, through the now hundreds of onlookers and devastated employees, looking for his son. “Go get your mother and all her friends,” he told his son with childlike excitement. “They’ll never see a fire like this again.” What?! Don’t worry, Edison calmed him. “It’s all right. We’ve just got rid of a lot of rubbish.” That’s a pretty amazing reaction. But when you think about it, there really was no other response. What should Edison have done? Wept? Gotten angry? Quit and gone home? What, exactly, would that have accomplished? You know the answer now: nothing. So he didn’t waste time indulging himself. To do great things, we need to be able to endure tragedy and setbacks.

We’ve got to love what we do and all that it entails, good and bad. We have to learn to find joy in every single thing that happens. Of course, there was more than just a little “rubbish” in Edison’s buildings. Years and years of priceless records, prototypes, and research were turned to ash. The buildings, which had been made of what was supposedly fire-proofed concrete, had been insured for only a fraction of their worth. Thinking they were immune to such disasters, Edison and his investors were covered for about a third of the damage. Still, Edison wasn’t heartbroken, not as he could have and probably should have been. Instead, it invigorated him. As he told a reporter the next day, he wasn’t too old to make a fresh start. “I’ve been through a lot of things like this. It prevents a man from being afflicted with ennui.” Within about three weeks, the factory was partially back up and running. Within a month, its men were working two shifts a day churning out new products the world had never seen. Despite a loss of almost $1 million dollars (more than $23 million in today’s dollars), Edison would marshal enough energy to make nearly $10 million dollars in revenue that year ($200-plus million today). He not only suffered a spectacular disaster, but he recovered and replied to it spectacularly.

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. It is the act of turning what we must do into what we get to do. We put our energies and emotions and exertions where they will have real impact. This is that place. We will tell ourselves: This is what I’ve got to do or put up with? Well, I might as well be happy about it.

Here’s an image to consider: the great boxer Jack Johnson in his famous fifteen-round brawl with Jim Jeffries. Jeffries, the Great White Hope, called out of retirement like some deranged Cincinnatus to defeat the ascendant black champion. And Johnson, genuinely hated by his opponent and the crowd, still enjoying every minute of it. Smiling, joking, playing the whole fight. Why not? There’s no value in any other reaction. Should he hate them for hating him? Bitterness was their burden and Johnson refused to pick it up. Not that he simply took the abuse. Instead, Johnson designed his fight plan around it. At every nasty remark from Jeffries’s corner, he’d give his opponent another lacing. At every low trick or rush from Jeffries, Johnson would quip and beat it back—but never lose his cool. And when one well-placed blow opened a cut on Johnson’s lip, he kept smiling—a gory, bloody, but nevertheless cheerful smile. Every round, he got happier, friendlier, as his opponent grew enraged and tired, eventually losing the will to fight. In your worst moments, picture Johnson: always calm, always in control, genuinely loving the opportunity to prove himself, to perform for people, whether they wanted him to succeed or not. Each remark bringing the response it deserved and no more—letting the opponent dig his own grave. Until the fight ended with Jeffries on the floor and every doubt about Johnson silenced. As Jack London, the famous novelist, reported from ringside seats: No one understands him, this man who smiles. Well, the story of the fight is the story of a smile. If ever a man won by nothing more fatiguing than a smile, Johnson won today. That man is us—or rather, it can be us if we strive to become like him. For we’re in our own fight with our own obstacles, and we can wear them down with our relentless smile (frustrating the people or impediments attempting to frustrate us). We can be Edison, our factory on fire, not bemoaning our fate but enjoying the spectacular scene. And then starting the recovery effort the very next day—roaring back soon enough. Your obstacle may not be so…

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.

A few years ago, in the middle of the financial crisis, the artist and musician Henry Rollins managed to express this deeply human obligation better than millennia of religious doctrine ever have: 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.

Shared purpose gives us strength.

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.

Memento mori, the Romans would remind themselves. Remember you are mortal.

Life is a process of breaking through these impediments—a series of fortified lines that we must break through. 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. 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. Knowing that life is a marathon and not a sprint is important. Conserve your energy. Understand that each battle is only one of many and that you can use it to make the next one easier. More important, you must keep them all in real perspective. 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. Never rattled. Never frantic. Always hustling and acting with creativity. Never anything but deliberate. Never attempting to do the impossible—but everything up to that line. Simply flipping the obstacles that life throws at you by improving in spite of them, because of them. And therefore no longer afraid. But excited, cheerful, and eagerly anticipating the next round.

What stood in the way became the way. What impeded action in some way advanced it.

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

Today, Bill Clinton rereads Marcus Aurelius every single year.

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.

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

I need to thank my master teacher and mentor Robert Greene, who not only subsidized my reading of many of the books I used as sources, but taught me the art of crafting a message and a book. His notes on my drafts were invaluable.