February 27, 2018

Notes From: The Obstacle Is The Way

Below is a collection of my notes from The Obstacle Is The Way by  Ryan Holiday.

The Obstacle Is The Way review

“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.

John D. Rockefeller had it—for him it was cool headedness and self-discipline. Demosthenes, the great Athenian orator, had it—for him it was a relentless drive to improve himself through action and practice. Abraham Lincoln had it—for him it was humility, endurance, and compassionate will.

“Bad companies are destroyed by crisis. Good companies survive them. Great companies are improved by them.”

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

While others are excited or afraid, we will remain calm and imperturbable. We will see things simply and straightforwardly, as they truly are—neither good nor bad. This will be an incredible advantage for us in the fight against obstacles.

The market was inherently unpredictable and often vicious—only the rational and disciplined mind could hope to profit from it. Speculation led to disaster, he realized, and he needed to always ignore the “mad crowd” and its inclinations.

“Oh, how blessed young men are who have to struggle for a foundation and beginning in life,” he once said. “I shall never cease to be grateful for the three and half years of apprenticeship and the difficulties to be overcome, all along the way.”

“Nothing makes us feel this way; we choose to give in to such feelings. Or, like Rockefeller, choose not to.”

“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.”

A mistake becomes training.

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.

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.

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.

no one said anything about not feeling it. No one said you can’t ever cry. Forget “manliness.” If you need to take a moment, by all means, go ahead. 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.

Does what happened keep you from acting with justice, generosity, self-control, sanity, prudence, honesty, humility, straightforwardness?

Do I need to freak out about this? And the answer—like it is for astronauts, for soldiers, for doctors, and for so many other professionals—must be: No, because I practiced for this situation and I can control myself. Or, No, because I caught myself and I’m able to realize that that doesn’t add anything constructive.

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.

A deer’s brain tells it to run because things are bad. It runs. Sometimes, right into traffic. We can question that impulse, disagree with it. And even can override the switch, examine the threat before we act. But this takes strength. It’s a muscle that must be developed. And muscles are developed by tension, by lifting and holding.

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.

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.

Perspective is everything.

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.

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

Everything changed for Clooney when he tried a new perspective. He realized that casting is an obstacle for producers, too—they need to find somebody, and they’re all hoping that the next person to walk in the room is the right somebody. Auditions were a chance to solve their problem, not his.

From Clooney’s new perspective, he was that solution. He wasn’t going to be someone groveling for a shot. He was someone with something special to offer and the answer to their prayers, not the other way around. That was what he began projecting in his auditions—not exclusively his acting skills but that he was the man for the job.

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

To harness the same power, recovering addicts learn the 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. This is how they focus their efforts. It’s a lot easier to fight addiction when you aren’t also fighting the fact that you were born, that your parents were monsters, or that you lost everything. That stuff is done. Delivered. Zero in one hundred chances that you can change it. So what if you focused on what you can change? That’s where you can make a difference. Behind the Serenity Prayer is a two-thousand-year-old Stoic phrase: “ta eph’hemin, ta ouk eph’hemin.” What is up to us, what is not up to us.

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

For all species other than us humans, things just are what they are. Our problem is that we’re always trying to figure out what things mean—why things are the way they are. As though the why matters.

Our perceptions determine, to an incredibly large degree, what we are and are not capable of. In many ways, they determine reality itself. When we believe in the obstacle more than in the goal, which will inevitably triumph?

As Laura Ingalls Wilder put it: “There is good in everything, if only we look for it.”

Blessings and burdens are not mutually exclusive. It’s a lot more complicated. Socrates had a mean, nagging wife; he always said that being married to her was good practice for philosophy.

Now the things that other people avoid, or flinch away from, we’re thankful for. When people are: —rude or disrespectful: They underestimate us. A huge advantage. —conniving: We won’t have to apologize when we make an example out of them.

—critical or question our abilities: Lower expectations are easier to exceed. —lazy: Makes whatever we accomplish seem all the more admirable.

Action is the solution and the cure to our predicaments.

We’ve all done it. Said: “I am so [overwhelmed, tired, stressed, busy, blocked, outmatched].” And then what do we do about it? Go out and party, treat ourselves, sleep in or wait. It feels better to ignore or pretend. But you know deep down that that isn’t going to truly make it any better. You’ve got to act. And you’ve got to start now.

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.

“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.”

Amelia Mary Earhart was an American aviation pioneer and author. Earhart was the first female aviator to fly solo across the Atlantic Ocean. She received the U.S. Distinguished Flying Cross for this accomplishment.


“While you’re sleeping, traveling, attending meetings, or messing around online, the same thing is happening to you. You’re going soft, not aggressive enough and 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.”

“proving that genius often really is just persistence in disguise.”

“Working at it works. It’s that simple. (But again, not easy.)”

“never in a hurry never worried never desperate never stopping short”

Epictetus: “persist and resist.” Persist in your efforts. Resist giving in to distraction, discouragement, or disorder.

There’s no need to sweat this or feel rushed. No need to get upset or despair. You’re not going anywhere—you’re not going to be counted out. You’re in this for the long haul.

It’s supposed to be hard. Your first attempts aren’t going to work. It’s goings 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. Stop looking for angels, and start looking for angles. There are options. Settle in for the long haul and then try each and every possibility, and you’ll get there.

When people ask where we are, what we’re doing, how that “situation” is coming along, the answer should be clear: We’re working on it. We’re getting closer. When setbacks come, we respond by working twice as hard.

Great entrepreneurs are: never wedded to a position never afraid to lose a little of their investment never bitter or embarrassed never out of the game for long They slip many times, but they don’t fall.

The one way to guarantee we don’t benefit from failure—to ensure it is a bad thing—is to not learn from it.

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

All these issues are solvable. Each would collapse beneath the process. We’ve just wrongly assumed that it has to happen all at once, and we give up at the thought of it. We are A-to-Z thinkers, fretting about A, obsessing over Z, yet forgetting all about B through Y.

Take your time, don’t rush. Some problems are harder than others. Deal with the ones right in front of you first. Come back to the others later. You’ll get there. The process is about doing the right things, right now. Not worrying about what might happen later, or the results, or the whole picture.

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.

The great psychologist Viktor Frankl, survivor of three concentration camps, found presumptuousness in the age-old question: “What is the meaning of life?” As though it is someone else’s responsibility to tell you. Instead, he said, the world is asking you that question. And it’s your job to answer with your actions.

We spend a lot of time thinking about how things are supposed to be, or what the rules say we should do. Trying to get it all perfect. We tell ourselves that we’ll get started once the conditions are right, or once we’re sure we can trust this or that. When, really, it’d be better to focus on making due with what we’ve got. On focusing on results instead of pretty methods.

Scratch the complaining. No waffling. No submitting to powerlessness or fear. You can’t just run home to Mommy. How are you going to solve this problem? How are you going to get around the rules that hold you back?

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.”

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.

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.

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.

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.

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.

We’re in the game of little defeating big. Therefore, Force can’t try to match Force.

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.

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. You’re acting like a real strategist. You aren’t just throwing your weight around and hoping it works. You’re not wasting your energy in battles driven by ego and pride rather than tactical advantage. Believe it or not, this is the hard way. That’s why it works. Remember, sometimes the longest way around is the shortest way home.

Before the invention of steam power, boat captains had an ingenious way of defeating the wickedly strong current of the Mississippi River. A boat going upriver would pull alongside a boat about to head downriver, and after wrapping a rope around a tree or a rock, the boats would tie themselves to each other. The second boat would let go and let the river take it downstream, slingshotting the other vessel upstream.


Remember, a castle can be an intimidating, impenetrable fortress, or it can be turned into a prison when surrounded. The difference is simply a shift in action and approach.

But think of an athlete “in the pocket,” “in the zone,” “on a streak,” and the seemingly insurmountable obstacles that fall in the face of that effortless state. Enormous deficits collapse, every pass or shot hits its intended target, fatigue melts away. Those athletes might be stopped from carrying out this or that action, but not from their goal. External factors influence the path, but not the direction: forward.

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. You always planned to do something. Write a screenplay. Travel. Start a business. Approach a possible mentor. Launch a movement. Well, now something has happened—some disruptive event like a failure or an accident or a tragedy. Use it.

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

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

Many saw themselves as mental athletes—after all, the brain is a muscle like any other active tissue. It can be built up and toned through the right exercises. Over time, their muscle memory grew to the point that they could intuitively respond to every situation. Especially obstacles.

No one is born a gladiator. No one is born with an Inner Citadel. If we’re going to succeed in achieving our goals despite the obstacles that may come, this strength in will must be built.

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. Your plan and the way things turn out rarely resemble each other. What you think you deserve is also rarely what you’ll get. Yet we constantly deny this fact and are repeatedly shocked by the events of the world as they unfold. It’s ridiculous. Stop setting yourself up for a fall.

You know you want to accomplish X, so you invest time, money, and relationships into achieving it. About the worst thing that can happen is not something going wrong, but something going wrong and catching you by surprise. Why? Because unexpected failure is discouraging and being beaten back hurts.

You know you’re not the only one who has to accept things you don’t necessarily like, right? It’s part of the human condition.

And things can always be worse. Not to be glib, but the next time you:   Lose money? Remember, you could have lost a friend. Lost that job? What if you’d lost a limb? Lost your house? You could have lost everything.

As the Stoics commanded themselves: Cheerfulness in all situations, especially the bad ones.

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?

The Germans have a word for it: Sitzfleisch. Staying power. Winning by sticking your ass to the seat and not leaving until after it’s over.

Our actions can be constrained, but our will can’t be. Our plans—even our bodies—can be broken. But belief in ourselves? No matter how many times we are thrown back, we alone retain the power to decide to go once more. Or to try another route. Or, at the very least, to accept this reality and decide upon a new aim.

If I can’t solve this for myself, how can I at least make this better for other people?

You can always remember that a decade earlier, a century earlier, a millennium earlier, someone just like you stood right where you are and felt very similar things, struggling with the very same thoughts. They had no idea that you would exist, but you know that they did. And a century from now, someone will be in your exact same position, once more.

Montaigne once wrote of an ancient drinking game in which participants took turns holding up a painting of a corpse inside a coffin and toasting to it: “Drink and be merry for when you’re dead you will look like this.”

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

Buy the Memento Mori medallion here.

We may not say it, but deep down we act and behave like we’re invincible. Like we’re impervious to the trials and tribulations of morality. That stuff happens to other people, not to ME. I have plenty of time left.

It doesn’t matter who you are or how many things you have left to be done, somewhere there is someone who would kill you for a thousand dollars or for a vile of crack or for getting in their way. A car can hit you in an intersection and drive your teeth back into your skull. That’s it. It will all be over. Today, tomorrow, someday soon.

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.

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.

Margaret Thatcher didn’t become known as the Iron Lady until she was sixty years old. There’s a saying in Latin: Vires acquirit eundo (We gather strength as we go). That’s how it works. That’s our motto.

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Chris Hughes

Chris loves learning, going on adventures, surfing and having fun. Chris on Google+