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The Obstacle is the Way

The Obstacle is the Way

Author: Ryan Holiday
Rating: 7/10
Last Read: September 2015

Quick Summary: The Obstacle is the Way is an accessible introductory book to the philosophy of stoicism.  Ryan Holiday draws from the stories of various historical figures and relates them to key principles of Stoic philosophy.  I find Stoicism to be a very helpful mindset to cultivate in my own life, and it is nice to see accessible books popularizing the wisdom of the Stoics.

If you like this book, I definitely recommend checking out the Meditations (Marcus Aurelius) and Enchiridon (Epictetus)

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.

My Highlights

Whatever we face, we have a choice: Will we be blocked by obstacles, or will we advance through and over them? --loc 113

Let’s be honest: Most of us are paralyzed. Whatever our individual goals, most of us sit frozen before the many obstacles that lie ahead of us. --loc 124

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. --loc 223

“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.” --loc 279

You must realize: Nothing makes us feel this way; we choose to give in to such feelings. --loc 288

Seen properly, everything that happens—be it an economic crash or a personal tragedy—is a chance to move forward. Even if it is on a bearing that we did not anticipate. --loc 311

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 --loc 313

Choose not to be harmed — and you won’t feel harmed. Don’t feel harmed — and you haven’t been. —MARCUS AURELIUS --loc 322

Nothing either good or bad, but thinking makes it so (Shakespeare) --loc 357

What such a man needs is not courage but nerve control, cool headedness. This he can get only by practice. —THEODORE ROOSEVELT --loc 377

During the Overland Campaign, Grant was surveying the scene through field glasses when an enemy shell exploded, killing the horse immediately next to him. Grant’s eyes stayed fixed on the front, never leaving the glasses. 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. That’s a man who has steadied himself properly. That’s a man who has a job to do and would bear anything to get it done. That’s nerve. --loc 384

Don’t forget, there are always people out there looking to get you. They want to intimidate you. Rattle you. Pressure you into making a decision before you’ve gotten all the facts. They want you thinking and acting on their terms, not yours. So the question is, are you going to let them? --loc 395

We must possess, as Voltaire once explained about the secret to the great military success of the first Duke of Marlborough, that “tranquil courage in the midst of tumult and serenity of soul in danger, which the English call a cool head.” --loc 400

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. --loc 408

Would you have a great empire? Rule over yourself. —PUBLIUS SYRUS --loc 416

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. --loc 418

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. --loc 430

‘What am I choosing to not see right now?’ What important things are you missing because you chose worry over introspection, alertness or wisdom? --loc 450

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. --loc 454

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. --loc 456

We defeat emotions with logic, or at least that’s the idea. Logic is questions and statements. With enough of them, we get to root causes (which are always easier to deal with). --loc 460

It might help to say it over and over again whenever you feel the anxiety begin to come on: I am not going to die from this. I am not going to die from this. I am not going to die from this. Or try Marcus’s question: Does what happened keep you from acting with justice, generosity, self-control, sanity, prudence, honesty, humility, straightforwardness? --loc 472

Don’t let the force of an impression when it first hit you knock you off your feet; just say to it: Hold on a moment; let me see who you are and what you represent. Let me put you to the test. —EPICTETUS --loc 481

Perceptions are the problem. They give us the “information” that we don’t need, exactly at the moment when it would be far better to focus on what is immediately in front of us: the thrust of a sword, a crucial business negotiation, an opportunity, a flash of insight or anything else, for that matter. --loc 495

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. --loc 505

Man does not simply exist but always decides what his existence will be, what he will become the next moment. By the same token, every human being has the freedom to change at any instant. —VIKTOR FRANKL --loc 523

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 Both matter, both can be effectively injected to change a situation that previously seemed intimidating or impossible. --loc 554

Perception precedes action. Right action follows the right perspective. --loc 571

In life our first job is this, to divide and distinguish things into two categories: externals I cannot control, but the choices I make with regard to them I do control. Where will I find good and bad? In me, in my choices. —EPICTETUS --loc 573

To argue, to complain, or worse, to just give up, these are choices. Choices that more often than not, do nothing to get us across the finish line. --loc 620

The trick to forgetting the big picture is to look at everything close up. —CHUCK PALAHNIUK --loc 633

Yet 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. --loc 651

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. --loc 662

It doesn’t matter whether this is the worst time to be alive or the best, whether you’re in a good job market or a bad one, or that the obstacle you face is intimidating or burdensome. What matters is that right now is right now. --loc 665

You’ll find the method that works best for you, but there are many things that can pull you into the present moment: Strenuous exercise. Unplugging. A walk in the park. Meditation. Getting a dog—they’re a constant reminder of how pleasant the present is. --loc 671

It’s not simply a matter of saying: Oh, I’ll live in the present. You have to work at it. Catch your mind when it wanders—don’t let it get away from you. Discard distracting thoughts. Leave things well enough alone—no matter how much you feel like doing otherwise. --loc 673

This is why 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. --loc 700

Now, how do you and I usually deal with an impossible deadline handed down from someone above us? We complain. We get angry. We question. How could they? What’s the point? Who do they think I am? We look for a way out and feel sorry for ourselves. --loc 708

Jobs refused to tolerate people who didn’t believe in their own abilities to succeed. Even if his demands were unfair, uncomfortable, or ambitious. --loc 711

Jobs learned to reject the first judgments and the objections that spring out of them because those objections are almost always rooted in fear. --loc 716

This is radically different from how we’ve been taught to act. Be realistic, we’re told. Listen to feedback. Play well with others. Compromise. Well, what if the “other” party is wrong? What if conventional wisdom is too conservative? It’s this all-too-common impulse to complain, defer, and then give up that holds us back. --loc 720

An entrepreneur is someone with faith in their ability to make something where there was nothing before. --loc 722

It’s our preconceptions that are the problem. They tell us that things should or need to be a certain way, so when they’re not, we naturally assume that we are at a disadvantage or that we’d be wasting our time to pursue an alternate course. When really, it’s all fair game, and every situation is an opportunity for us to act. --loc 757

How about that business decision that turned out to be a mistake? Well, you had a hypothesis and it turned out to be wrong. Why should that upset you? It wouldn’t piss off a scientist, it would help him. --loc 775

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. --loc 792

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). --loc 809

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. --loc 811

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. Or treat ourselves. Or sleep in. Or wait. --loc 869

We forget: In life, it doesn’t matter what happens to you or where you came from. It matters what you do with what happens and what you’ve been given. --loc 872

Consider this mind-set. never in a hurry never worried never desperate never stopping short --loc 1003

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. --loc 1006

What is defeat? Nothing but education; nothing but the first steps to something better. —WENDELL PHILLIPS --loc 1025

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. --loc 1051

The one way to guarantee we don’t benefit from failure—to ensure it is a bad thing—is to not learn from it. To continue to try the same thing over and over --loc 1068

“Don’t think about winning the SEC Championship. Don’t think about the national championship. 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.” --loc 1086

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. --loc 1094

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. --loc 1188

A very Zen stance from our boy M. Aurelius:

The cucumber is bitter? Then throw it out. There are brambles in the path? Then go around. That’s all you need to know. —MARCUS AURELIUS --loc 1199

Whoever cannot seek the unforeseen sees nothing, for the known way is an impasse. —HERACLITUS --loc 1254

Take a step back, then go around the problem. Find some leverage. Approach from what is called the “line of least expectation.” --loc 1282

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. --loc 1316

Wise men are able to make a fitting use even of their enmities. —PLUTARCH --loc 1320

The great strategist Saul Alinsky believed that if you “push a negative hard enough and deep enough it will break through into its counterside.” Every positive has its negative. Every negative has its positive. The action is in the pushing through—all the way through to the other side. Making a negative into a positive. --loc 1369

The best men are not those who have waited for chances but who have taken them; besieged chance, conquered the chance, and made chance the servitor. —E. H. CHAPIN --loc 1420

Great commanders look for decision points. For it is bursts of energy directed at decisive points that break things wide open. They press and press and press and then, exactly when the situation seems hopeless—or, more likely, hopelessly deadlocked—they press once more. --loc 1464

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 --loc 1473

Nothing can ever prevent us from trying. Ever. --loc 1479

It’s an infinitely elastic formula: In every situation, that which blocks our path actually presents a new path with a new part of us. If someone you love hurts you, there is a chance to practice forgiveness. If your business fails, now you can practice acceptance. If there is nothing else you can do for yourself, at least you can try to help others. --loc 1483

Will is our internal power, which can never be affected by the outside world. It is our final trump card. If action is what we do when we still have some agency over our situation, the will is what we depend on when agency has all but disappeared. --loc 1494

True will is quiet humility, resilience, and flexibility; the other kind of will is weakness disguised by bluster and ambition. --loc 1500

It’s much easier to control our perceptions and emotions than it is to give up our desire to control other people and events. --loc 1571

These lessons come harder but are, in the end, the most critical to wresting advantage from adversity. 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. --loc 1574

Nobody is born with a steel backbone. We have to forge that ourselves. --loc 1605

We craft our spiritual strength through physical exercise, and our physical hardiness through mental practice (mens sana in corpore sano—sound mind in a strong body). --loc 1606

During the good times, we strengthen ourselves and our bodies so that during the difficult times, we can depend on it. We protect our inner fortress so it may protect us. --loc 1620

Offer a guarantee and disaster threatens. —ANCIENT INSCRIPTION AT THE ORACLE OF DELPHI --loc 1639

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. --loc 1649

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.” --loc 1654

“Nothing happens to the wise man against his expectation,” he wrote to a friend. “...nor do all things turn out for him as he wished but as he reckoned—and above all he reckoned that something could block his plans.” --loc 1662

The only guarantee, ever, is that things will go wrong. The only thing we can use to mitigate this is anticipation. --loc 1677

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. --loc 1693

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. --loc 1731

It is far easier to talk of the way things should be. It takes toughness, humility, and will to accept them for what they actually are. It takes a real man or woman to face necessity. --loc 1734

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. --loc 1829

Determination, if you think about it, is invincible. Nothing other than death can prevent us from following Churchill’s old acronym: KBO. Keep Buggering On. --loc 1895

Pride can be broken. Toughness has its limits. But a desire to help? No harshness, no deprivation, no toil should interfere with our empathy toward others. Compassion is always an option. Camaraderie as well. That’s a power of the will that can never be taken away, only relinquished. --loc 1958

Help your fellow humans thrive and survive, contribute your little bit to the universe before it swallows you up, and be happy with that. Lend a hand to others. Be strong for them, and it will make you stronger. --loc 1970

When a man knows he is to be hanged in a fortnight, it concentrates his mind wonderfully. —DR. JOHNSON --loc 1973

Memento mori, the Romans would remind themselves. Remember you are mortal. --loc 1994

We forget how light our grip on life really is. Otherwise, we wouldn’t spend so much time obsessing over trivialities, or trying to become famous, make more money than we could ever spend in our lifetime, or make plans far off in the future. --loc 1998

The paths of glory, Thomas Gray wrote, lead but to the grave. --loc 2001

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. --loc 2013

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. --loc 2114

The Latin translation for the title of Enchiridion—Epictetus’s famous work—means “close at hand,” or as some have said, “in your hands.” That’s what the philosophy was meant for: to be in your hands, to be an extension of you. Not something you read once and put up on a shelf. It was meant, as Marcus once wrote, to make us boxers instead of fencers—to wield our weaponry, we simply need to close our fists. --loc 2161

Gregory Alan Isakov with the Colorado Symphony

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