The Obstacle is the Way by Ryan Holiday

Book Summary

This is a comprehensive summary of “The Obstacle is the Way” by Ryan Holiday. The book explores the timeless art of turning trials into triumph.

what’s in it for me? discover how to transform even the greatest obstacles into advantages.#

Introduction

welcome to the chapter of ryan holiday's the obstacle is the way.

i'm your narrator, ryan.

so, this chapter basically boils down to a single key message.

here it is.

each obstacle, each impediment, each thing that seems to be blocking the path to success is itself the path to success.

in other words, every obstacle, everything that seems to be standing in your way is itself the way.

hence, the title.

marcus aurelius, the roman emperor and stoic philosopher put it like this.

the impediment to action advances action.

what stands in the way becomes the way.

that's a quote.

now, i want to make something clear.

this is not about seeing the silver lining in every situation.

it's not about being a cup half full kind of person and you don't have to throw on a pair of rose-colored glasses.

the point is that seeing the opportunities hidden in every obstacle is not about being relentlessly optimistic.

rather, it's about being clear-eyed, logical, reasonable, prepared, and pragmatic.

prepared for whatever life might throw at you and pragmatic both in how you perceive your circumstances and in how you respond to them.

it's not about ignoring obstacles.

it's about approaching them in the most effective way.

this chapter has three sections just like the book.

perception, action, and will.

these are the three ingredients to flipping any situation to taking a negative and turning it into a positive.

perception is the starting point.

learning to regard what most people would call an obstacle, say an economic downturn, a traffic jam, a personal disability, anything, taking that obstacle and seeing it as a path to success.

then comes action.

perceiving the path is the beginning but it won't bring you much unless you act, unless you actually take that path.

and then comes will.

the energy, the determination, the will to stay on the path, to keep walking even when the going gets tough.

all of this is simple enough but that doesn't mean it's easy to put into practice.

so let's look at some examples of people who have done it.

people who've taken disadvantages, setbacks, hardships, inauspicious circumstances and then flipped them over, revealing what they truly were, hidden pathways to success.

perception: the opportunity in adversity.#

chapter 1.

perception.

the opportunity in adversity.

john d. rockefeller, the famous oil baron, learned the art of perception in the crucible of crisis.

in 1855 rockefeller was 16 years old.

he was just starting out as a bookkeeper with aspirations to become an investor.

two years later the panic of 1857 struck, sending america spiraling into a crippling financial crisis, the greatest market depression in history.

all around rockefeller people began abandoning careers in finance.

they were afraid, panicked, perceiving what was happening as a horrible disaster.

rockefeller could have done the same.

he could have panicked, scrambled to switch careers but he didn't.

rather than losing his nerve he decided to treat this economic cataclysm as an opportunity to learn, to observe, to figure out what he might do right in the future by watching what people were doing wrong in the present.

in other words he leveraged the power of perception.

perception is all about the meaning you impose on events.

is a financial crisis a terrifying disaster, something to run from?

or is it a learning opportunity, something to observe?

it's up to you.

one way of perceiving it deprives you of power, the other way gives you power.

and we all know what kind of power rockefeller accrued.

by the time he was 40 years old rockefeller alone controlled 90% of oil refineries in the united states.

the secret to his success was an investment strategy driven by level-headed logic, not reactive emotions.

he didn't invest because the market told him to or because everyone else was doing it.

and when he did make investments he was able to remain confident and see things through even as others sold their shares out of fear.

rockefeller was wise, resilient, adaptable and completely calm amid the chaos.

these characteristics constituted the foundation on which he built his oil empire.

so how can we be a bit more like rockefeller?

well here are three tips.

if you're faced with a major obstacle, something that's truly daunting or intimidating or frightening, try to first focus on what you can control and ignore what you can't.

second, remain objective.

don't get caught up in subjective emotions or projections.

and third, stay in the present moment.

don't spiral into regrets about the past or worries about the future.

you already possess the qualities necessary to perceive the opportunity in any obstacle.

logic, objectivity, reason, cool-headedness, you already possess those qualities and deploying them is just a matter of discipline, practice and habit.

perception: recognizing your power.#

chapter 2.

perception.

recognizing your power.

in the 1960s, the then-celebrated boxer reuben hurricane carter was accused of a triple homicide.

now, carter was innocent.

he'd done nothing wrong, let alone murder three people.

but still, he was given three life sentences and sent to prison.

at this point, carter faced a choice.

he could relinquish his power and submit to the situation, accepting the system's perception of him as a criminal.

or he could hold on to his power despite the situation and act despite his imprisonment like the innocent man that he was.

he chose the path of power.

as he entered prison, he announced to the warden that he refused to be treated like a prisoner, that, though he didn't wield the power to walk free, he would never be powerless.

he still had power over his perception.

he still had power over his choices.

he refused to perceive himself as a prisoner and he chose to act accordingly, refusing everything that had anything to do with the prison.

uniforms, prison food, visitors, parole hearings, he refused them all.

and he used his time to study history, philosophy, the law, anything that would help him overturn his case.

carter entered prison when he was 29 years old and he left when he was 49, his case having finally been overturned.

he spent 19 years in prison, but carter wouldn't have said those years were stolen just as he refused to say he was powerless.

he may have been in a horrible place, but he was always in control, in control of his choices, his thoughts, his reactions, his perception.

that's a kind of control, a kind of power that no one could deprive him of.

and you know what?

we all possess this power.

people may betray you, fate may deal you a crummy hand, you may face setback after setback, but in almost every situation you still have the power of your perception.

how will you choose to see the situation?

how will you choose to react?

remember that good and bad are concepts that we impose.

in reality there's a situation, an event.

the story we tell ourselves about this event, that's what makes it good or bad or anything in between.

the story you tell or don't tell is entirely up to you.

that's the power of perception.

that's what reuben carter knew.

so what will you choose?

how will you perceive the obstacles before you?

the power is yours.

it always has been and it always will be.

perception: altering your perspective.#

chapter 3.

perception.

altering your perspective during the peloponnesian war, the general pericles and his men were at sea when suddenly darkness fell like a curtain.

a solar eclipse had caused day to turn to night.

pericles' soldiers, surprised, confused, began to panic.

but their leader, pericles, remained calm.

he removed his cloak and approached the man in charge of steering the ship.

holding the cloak in front of the man's face, he asked whether the darkness frightened him.

the man said, of course not.

pericles replied, and this is a rough paraphrase, then what the heck are you afraid of?

why fear one form of darkness but not the other?

it's an entertaining anecdote, but it has a profound point.

perspective is everything.

the men on the ship had attributed meaning to the solar eclipse.

they'd perceived it as ominous, a portent of ills to come.

in other words, they'd chosen a disempowering perception.

darkness caused by the overlap of celestial bodies is ominous.

pericles, on the other hand, chose an empowering perception.

one kind of darkness is the same as any other.

so, unless you're irrationally afraid of the dark, there's nothing to fear.

the way that you look at something, the way that you perceive it, is what determines whether it's frightening or exciting, fun or miserable, good or bad, and the perception you choose is always up to you.

here's another example.

when george clooney first came to hollywood, he was just like any other actor.

he struggled.

for years, each audition ended in a rejection, and this hurt.

he was talented, he knew that, but no one seemed to see it.

so, he became dejected, blaming the system for overlooking his obvious talent.

now, we all do this all the time.

we blame companies for not hiring us, or we blame attractive strangers for not flirting with us.

we want to be seen, we want to be chosen, and we get hurt when we're not.

but this is only one way of perceiving the situation.

there is a way to flip it.

so, back to clooney for a second.

clooney realized that landing a role was not his obstacle.

it was the film producers.

they were the ones who desperately needed to find the right actor.

they needed him, not the other way around.

he wasn't a humble nobody hoping for his big break.

he was the dream actor they'd been waiting for.

this simple perspective shift changed everything.

in subsequent auditions, he projected competence and confidence, not only as an actor, but as someone who'd do what needed to be done, someone who, on camera and off, would make the producers' lives easy.

next up, we'll be looking at action.

but, remember, the action you take depends on the perspective you take.

if you perceive something in the right way, you'll act in the right way, that is, in the way most likely to bring success.

so, whatever situation you find yourself in, ask yourself, does my perspective benefit me?

or am i afraid or daunted or insecure because i'm looking at this the wrong way?

am i mistaking an eclipse for an evil portent?

am i regarding myself as a problem when i'm actually the solution?

you control your perception, and perception is everything.

action: the power of discipline.#

chapter 4 action – the power of discipline recognizing the power you have in every situation, defanging daunting situations by shifting your perspective, realizing that a problem is only a problem if you perceive it that way – all of this is the beginning.

next comes action.

you don't need to be naively optimistic to act.

remember, perception doesn't mean seeing everything through rose-tinted glasses.

seeing things clearly, reasonably, logically, coolly – that's what perception is all about.

it's not about ignoring or diminishing problems.

it's about stripping away emotion, subtracting meaning rather than imposing it.

a task may truly be difficult, but you don't need to make it more difficult by losing your head.

same goes for action.

it's not about ignoring potential difficulties.

it's not about being brash.

it's about being bold.

look at the situation, look at it rationally and logically, and then, knowing exactly what you're up against, act.

if you can be flexible, persistent, disciplined, tackling each task one at a time, you can achieve whatever you set out to do.

take aim at your target and keep that target in mind, but then focus all your energy on the steps necessary to get there.

that is the key to effective action.

let's take an example.

demosthenes was the greatest orator of ancient athens, but if you'd met him in his early years, you'd never have predicted his future success.

as a boy, he was small, weak, effeminate, and sickly.

his father died when he was seven, leaving him a handsome inheritance, which his guardians then stole.

with no money to pay tutors, demosthenes got no education.

oh, and he had a speech impediment.

abandoned, betrayed, awkward, downtrodden, there was hardly an obstacle demosthenes didn't face.

but instead of being utterly crushed by his circumstances, and let's face it, most of us would have been, he came up with a plan.

and he had the steel-hard discipline forged in the fire of hardship to follow through.

to conquer his speech impediment, he recited speeches.

he did this while running, while yelling into the wind, while his mouth was full of pebbles.

and he taught himself to recite entire speeches after taking only one breath.

and then he studied.

in a room he'd built for himself underground, he studied the law, he practiced more speeches, he refined arguments.

he knew that studying so much would be hard, so he shaved half his head so that he'd be too ashamed to appear in public.

he lived it and breathed it.

discipline, discipline, discipline.

each action a step toward his goal.

and what was that goal?

nothing less than taking his guardians to court and reclaiming his inheritance.

long story short, he got what remained of his inheritance, single-handedly out-arguing every lawyer that was thrown at him.

but by then, money was kind of beside the point.

he'd established himself as a dazzling orator and a shrewd student of the law.

gifts worth more than any inheritance.

so what's your goal?

whatever it is, you can learn from demosthenes.

first, develop a strategic vision.

and then persist.

getting to where you want to be is only a matter of discipline.

chapter 5.

action: trust the process.#

action.

trust the process.

let's take a moment and dissect demosthenes' process.

he had a big goal, reclaim his stolen inheritance.

but he didn't immediately try to accomplish that goal.

he didn't take them to court as soon as he could.

he followed a process, focusing all his energies on the small steps that would get him from point a to point z. look, it seems obvious, but it's all too common for people, when pursuing some huge goal, to try to skip the small steps, to jump from a to z without taking care of b, c, d, and all the rest.

demosthenes was disciplined.

he was persistent.

he was determined.

but he also had a process.

or, in the words of nick saban, head coach of one of the best college football teams in the united states, the university of alabama's crimson tide, he had the process.

the process says, you're facing a big daunting task?

forget about the big picture.

don't worry about winning the national championships.

don't worry about winning a legal case, even though you have a speech impediment.

ignore that.

focus on what needs to happen right now.

focus on this task, this drill, this speech exercise, this single small step.

the path to success is precisely that, a path.

all paths must be walked one step at a time, so focus on this step, execute it well, and then focus on the next step.

the thing about the process is that it's soothing.

the path ahead is long, filled with twists and turns and unknown dangers.

no matter.

that does not concern us.

all that concerns us is this step, then this one.

steps executed perfectly with total focus.

it sounds obvious, but think about it.

how many times have you not pursued a goal because it seems too big?

i can't write a book.

that's way too much work.

where would i even start?

that's where the process comes in.

don't focus on the end goal.

focus on what's right in front of you, what you can do now, no matter how small.

can you write a sentence?

the process can take care of the rest.

accomplishing major goals is not about brilliance or superhuman strength.

it's not about natural endowments or lucky breaks.

it's about taking one step after the other, completing one small task, and then the next, and the next.

trust the process.

relax into it.

that's the only way to walk the path to success, whether you're a linebacker, an aspiring orator, or someone with humble dreams of someday writing a book.

chapter 6.

action: it might not work.#

action.

it might not work.

we're about to move to the next section, will.

but before we do, a quick reminder.

it's not always going to work.

you may flip an obstacle with ease, shifting your perspective, perceiving it in the most advantageous way possible, seizing your power.

you may then take correct action, setting a goal, breaking it down into individual steps, executing each step with excellence and total focus.

still, it might not work.

some obstacles are insurmountable.

some paths, through no fault of our own, are not passable.

if you run up against an obstacle that simply cannot be overcome, keep in mind, you have tried.

nothing can and nothing ever should prevent you from trying.

if you've tried and persisted in trying and realized that no amount of trying will flip this obstacle, this boulder in your path, then you can deploy again the skills that you've already learned.

use this as an opportunity to reinforce other skills or qualities in yourself.

that's the beauty of the formula.

so, you've worked and worked on your relationship, but your partner leaves you anyway?

buried in the sadness and anger is an opportunity, an opportunity to foster the qualities of forgiveness and selfless love.

or the company you founded ends up floundering?

you can practice accepting that some things are out of your hands.

if you've done your best, your true best, there's nothing else you can do, and there's nothing else you're required to do.

action implies risk.

the risk that things won't go your way.

the risk that you'll be thwarted by external events.

and that's fine.

sometimes there's nothing you can do.

things won't work out the way you want.

what you can always do, though, is be prepared.

not afraid, not daunted.

prepared.

willing to accept whatever happens and ready to move on boldly and with acceptance and eager to see what might happen next.

that way, there are no failures, only lessons.

with that in mind, let's move on to the final section.

will: accept what you can’t change, and change what you can.#

chapter 7.

will.

accept what you can't change and change what you can.

will is often confused with really, really wanting something.

people think, if i want this thing really badly, then i've got it.

will.

but true will has more to do with acceptance than with force.

it's our final refuge in the face of trying circumstances.

it's an internal power, the thing that enables us to do what we discussed in the last chapter.

accept with grace and humility what we can't change and be resilient enough and flexible enough to move on when we don't get our way.

the great stoic thinkers, marcus aurelius, epictetus, seneca, were masters of will.

they focused their will by keeping a single question front and center.

what can i control and what can i not control?

and they knew that we truly only control one thing, our mind.

everything external to the mind, other people's actions, natural events, the inevitability of death, is outside our control.

and all that our minds contain are emotions, judgments, attitudes, responses, decisions.

well, these are within our control.

so what can you do with this information?

well, you can build what the stoics called an inner citadel, a metaphorical internal structure that is impervious to the vagaries of the external world.

the stoics stress that no one is born with an inner citadel.

and this is important.

you have to build your citadel.

you have to work at it.

it's often assumed that abilities are inborn.

most people assume that if they were born with a disadvantage, they're stuck with it for life.

but this is simply not true.

for example, consider theodore roosevelt.

he was born with terrible asthma.

he was born privileged with an able mind, but even slight exercise would result in an attack and he'd have to stay in bed for weeks.

most people would have resigned themselves to their fate, but not roosevelt.

with the encouragement and help of his father, he battled the asthma he'd been born with.

at the age of 12, in a gym constructed by his father, he began exercising, strengthening his upper body, slowly improving his lungs.

and 10 years later, his asthma was all but gone.

he'd worked away his weakness.

life put many obstacles in roosevelt's path.

his wife died, then his mother.

he had to contend with fierce political opponents.

attempts were made on his life, but he was prepared.

he'd built his strength and kept building it every day throughout his life.

so ask yourself, are you prepared for what life will throw at you?

because it will throw things.

loss, reversals of fate, hardship, and unhappiness.

there's nothing you can do about that.

what you can do is be prepared.

you can, like roosevelt, strengthen your body.

what kind of structure must you create?

what kind of inner citadel?

so that when the hardship comes, you're strong enough to accept it and continue on the path.

chapter 8.

will: be ready to persevere.#

will.

be ready to persevere.

after fighting in troy for 10 long years, odysseus, the protagonist of homer's epic poem, the odyssey, finally set sail for home.

what happens then?

10 years of obstacles.

on his ill-fated journey home, he is held prisoner, faces numerous temptations, loses all of his men, encounters dangerous whirlpools, and even fights off a cyclops and a six-headed monster.

eventually, though, after 20 years of war and hardship, he does get home, reunited at last with his wife and son.

how did he do it?

what enabled him to keep going, to keep fighting despite a world of hardship?

the short answer?

perseverance.

perseverance is often confused with persistence.

but the two are not the same.

persistence is throwing everything you've got at a single problem, a single obstacle.

it's like trying to breach the gates of troy again and again until you find the solution, just like odysseus thought up the trojan horse.

perseverance is different.

it's being in it for the long haul, being ready to face all the obstacles, the temptations, the whirlpools, the cyclops, and the six-headed monster, everything that life will put in your path.

it's a matter of will.

if persistence is like energy, then perseverance is like endurance.

odysseus had ample opportunity to despair, to give up, to give in.

but he didn't.

he persisted through it all, through everything the gods threw at him.

despair?

that wouldn't have brought him any closer to ithaca.

complaining?

same story.

he had the endurance to work through it all, one obstacle after another, until he'd achieved his aim and reached his beloved home.

we may not all have it as hard as odysseus, but we're all on our own odyssey.

life is a series of obstacles.

if you flip one, get ready to flip the next.

but if you can't overcome this one, don't quit.

persevere.

it's up to you whether you keep trying.

it's up to you whether you tap out or get up.

so why stand in your own way?

you've got it in you to get there, even if, like odysseus, it takes 20 years.

chapter 9, our last chapter.

will: meditate on death and get ready to begin again.#

will.

meditate on death and get ready to begin again.

it may sound morbid, but we're all going to die.

yeah, but not today, you might think.

and that may be true.

i certainly hope it is.

but each day that we don't die, death draws nearer.

death is out of our control.

it is not something that we should worry about.

but it is something that we should think about, because it can give our life renewed purpose, renewed urgency.

you don't know when death will come.

so the time to take the reins, to focus on the things you can control, is right now.

death is an insurmountable obstacle.

there's certainly no way around it.

but we can still use it.

in the face of death, all other obstacles and irritants seem far less troublesome.

why get upset when you get cut off in traffic?

why worry too much?

why not be gracious, kind, appreciative?

death is coming.

why not live life the right way?

if you can do this, if you can turn even this most dread obstacle to your advantage, then what obstacle can't you overcome?

one last thing before we conclude.

remember that you'll always have to begin again.

one obstacle down?

great, but get ready for the next one.

and get ready for overcoming an obstacle to create a new obstacle.

this might sound exhausting, but the more you do it, the more you flip obstacles, the better you'll get, and the better the opportunities you'll find will become.

so keep going.

unshaken.

unhurried.

moving with creativity and determination.

knowing that obstacles aren't to be feared.

they're to be embraced.

they don't stand in the path.

they are the path.

so get ready to begin again and bring on the obstacles.

final summary#

Conclusion

you just listened to the chapter to, the obstacle is the way by ryan holiday.

perception, action, will.

these are the three steps to turning obstacles into opportunities, adversity into advantage.

by perceiving obstacles objectively, recognizing your power and altering your perception, by acting with discipline and diligence, trusting the process, and by deploying your will, persevering no matter what, by leveraging these steps, you'll be able to transform life's obstacles into the fire that fuels your success.

thanks for listening, and i hope to see you in the next chapter.

The Obstacle is the Way

Table of Contents

Book Summary

what’s in it for me? discover how to transform even the greatest obstacles into advantages.#

perception: the opportunity in adversity.#

perception: recognizing your power.#

perception: altering your perspective.#

action: the power of discipline.#

action: trust the process.#

action: it might not work.#

will: accept what you can’t change, and change what you can.#

will: be ready to persevere.#

will: meditate on death and get ready to begin again.#

final summary#

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