Obstacle Is the Way by Ryan Holiday - Summary & Quotes

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Three Takeaways

Note: The following are excerpts from The Obstacle is the Way: The Ancient Art of Turning Adversity to Advantage by Ryan Holiday.

1. Alter Your Perspective

Once as the Athenian general Pericles cast off on a naval mission in the Peloponnesian War, the sun was eclipsed and his fleet of 150 ships was cast into darkness. Surprised by this unexpected and confusing event, his men were thrown into a state of panic. Unlike the crew, Pericles was undaunted. He walked up to a lead steersman, removed the cloak he was wearing, and held it up around the man’s face. He asked the man if he was scared of what he saw.No, of course not. So what does it matter, Pericles replied, when the cause of the darkness differs? The Greeks were clever. But beneath this particular quip is the fundamental notion that girds not just Stoic philosophy but cognitive psychology: 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. The Greeks understood that we often choose the ominous explanation over the simple one, to our detriment. That we are scared of obstacles because our perspective is wrong—that a simple shift in perspective can change our reaction entirely. The task, as Pericles showed, is not to ignore fear but to explain it away. Take what you’re afraid of—when fear strikes you—and break it apart.

Remember: We choose how we’ll look at things. We retain the ability to inject perspective into a situation. 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.

It’s your choice whether you want to put I in front of something (I hate public speaking. I screwed up. I am harmed by this). These add an extra element: you in relation to that obstacle, rather than just the obstacle itself. And with the wrong perspective, we become consumed and overwhelmed with something actually quite small. So why subject ourselves to that? The right perspective has a strange way of cutting obstacles—and adversity—down to size. But for whatever reason, we tend to look at things in isolation. We kick ourselves for blowing a deal or having to miss a meeting. Individually, that does suck—we just missed 100 percent of that opportunity.

2. What's Right is What Works

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.” Because you’re never going to find that kind of perfection. Instead, do the best with what you’ve got. Not that pragmatism is inherently at odds with idealism or pushing the ball forward. 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. 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.

3. Find A Way Around

The popular image of George Washington in American lore is of a brave and bold general, towering over everything he surveyed, repelling the occupied and tyrannical British. Of course, the true picture is a little less glorious. 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. His most glorious “victory” wasn’t even a direct battle with the British. Instead, Washington, nearly at the end of his rope, crossed the Delaware at dawn on Christmas Day to attack a group of sleeping German mercenaries who may or may not have been drunk. He was actually better at withdrawing than at advancing—skilled at saving troops that otherwise would have been lost in defeat. Washington rarely got trapped—he always had a way out. Hoping simply to tire out his enemy, this evasiveness was a powerful weapon—though not necessarily a glamorous one. It’s not surprising then, as the general of the Continental Army and the country’s first president, that his legacy has been whitewashed and embellished a little. And he’s not the only general we’ve done it for. The great myth of history, propagated by movies and stories and our own ignorance, is that wars are won and lost by two great armies going head-to-head in battle. It’s a dramatic, courageous notion—but also very, very wrong.

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. When you’re at your wit’s end, straining and straining with all your might, when people tell you you look like you might pop a vein . . .

Take a step back, then go around the problem. Find some leverage. Approach from what is called the “line of least expectation. What’s your first instinct when faced with a challenge? Is it to outspend the competition? Argue with people in an attempt to change long-held opinions? Are you trying to barge through the front door? Because the back door, side doors, and windows may have been left wide open. Whatever you’re doing, it’s going to be harder (to say nothing of impossible) if your plan includes defying physics or logic. Instead, think of Grant realizing he had to bypass Vicksburg—not go at it—in order to capture it. 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. 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.

Part of the reason why a certain skill often seems so effortless for great masters is not just because they’ve mastered the process—they really are doing less than the rest of us who don’t know any better. They choose to exert only calculated force where it will be effective, rather than straining and struggling with pointless attrition tactics. As someone once put it after fighting Jigoro Kano, the legendary five-foot-tall founder of judo, “Trying to fight with Kano was like trying to fight with an empty jacket!” That can be you.  Being outnumbered, coming from behind, being low on funds, these don’t have to be disadvantages. They can be gifts. Assets that make us less likely to commit suicide with a head-to-head attack. These things force us to be creative, to find workarounds, to sublimate the ego and do anything to win besides challenging our enemies where they are strongest. These are the signs that tell us to approach from an oblique angle. In fact, having the advantage of size or strength or power is often the birthing ground for true and fatal weakness. 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. We’re in the game of little defeating big. Therefore, Force can’t try to match Force. Of course, when pushed, the natural instinct is always to push back. But martial arts teach us that we have to ignore this impulse. We can’t push back, we have to pull until opponents lose their balance. Then we make our move. The art of the side-door strategy is a vast, creative space. And it is by no means limited to war, business, or sales.

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Learn more about The Obstacle Is The Way on Amazon.

Buy The Obstacle Is The Way: Print | Kindle | Audiobook

If you enjoyed this summary, please consider buying me a coffee to caffeinate my reading sessions.