Ryan Holiday | ISBN: 1591846358 | Finished: 7/2014 | Rating: 9/10
The Obstacle is the Way Summary
Ryan Holiday is one of those people you read about and can’t help but admire. He dropped out of college to work with Robert Greene and has advised some extremely successful authors including Tim Ferriss and Tucker Max. He also served as the director of marketing for American Apparel. He owes much of his success to the ideas and lessons he learned from stoicism.
This brings us back to The Obstacle is the Way, which is the first book on stoicism I’ve ever read, and it’s an absolute gem. You may be asking yourself “What does stoicism have to do with art?”, but that is the wrong question. The real question is “How does stoicism help me in life?” First, let’s explore what stoicism is.
Stoicism is a systematic philosophy, dating from around 300 b.c., that held the principles of logical thought to reflect a cosmic reason instantiated in nature.
What this means in plain terms is stoicism forces you to look at every situation logically. Instead of letting your emotions take over your decision making, you must look at every situation objectively to find a logical solution. This may seem hard for artists, who are normally very passionate people, but I have found removing your emotions from a problem makes the solution much clearer.
The book is split into three parts: perception, action, and will.
Action: This section explores getting started, following a process, using unconventional methods, and turning obstacles into opportunities. Even if you are able to recognize problems through perception, without action, nothing will be fixed.
Will: In the final section, Ryan explores having discipline, anticipating the worst, perseverance, and being ready to start over. Perception and action will only get you so far, if your will is broken. Knowing how everything is connected and acknowledging things happen for a reason is the glue that holds you together.
This book has an incredible number of great examples to back up each point. Without great stories to back it up, philosophy is just someone’s theory. Luckily, Holiday explores how some of the most influential people in history who have used and adopted stoic principles. He provides examples ranging from Roman emperor Marcus Aurelius to US President Barack Obama, and many people in-between. If you are interested in reading these stories, I highly recommend picking up this book.
“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.” – Ryan Holiday
Kindle Highlights for The Obstacle is the Way
(LOCATIONS are for Kindle)
The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph
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.
The impediment to action advances action. What stands in the way becomes the way.
turning obstacles upside down.
what impedes us can empower us.
he truly saw each and every one of these obstacles as an opportunity to practice some virtue: patience, courage, humility, resourcefulness, reason, justice, and creativity.
he proved himself worthy of it.
We might not be emperors, but the world is still constantly testing us.
Every obstacle is unique to each of us.
Fear. Frustration. Confusion. Helplessness. Depression. Anger.
We’re trying to get somewhere, but something stands in the way. So we do nothing.
only one thing is at fault: our attitude and approach.
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.
We have no idea what to do.
turn those very obstacles,
into launching pads for themselves.
method and a framework for understanding, appreciating, and acting upon the obstacles life throws at us.
“Bad companies are destroyed by crisis. Good companies survive them. Great companies are improved by them.”
transform weakness into strength.
obstacles became fuel for the blaze that was their ambition.
turn every obstacle into an advantage.
unstuck, unfucked, and unleashed.
Not “be positive” but learn to be ceaselessly creative and opportunistic.
“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.”
We’re soft, entitled, and scared of conflict.
Abundance can be its own obstacle,
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
Perception, Action, and the Will.
WHAT IS PERCEPTION? It’s how we see and understand what occurs around us—and what we decide those events will mean.
The market was inherently unpredictable and often vicious—only the rational and disciplined mind could hope to profit from it.
He was inclined to see the opportunity in every disaster.
the greater the chaos, the calmer Rockefeller would become,
Warren Buffet’s famous adage to “be fearful when others are greedy and greedy when others are fearful.”
You will come across obstacles in life—fair and unfair. And you will discover, time and time again, that what matters most is not what these obstacles are but how we see them, how we react to them, and whether we keep our composure. You will learn that this reaction determines how successful we will be in overcoming—or possibly thriving because of—them.
Desperation, despair, fear, powerlessness—these reactions are functions of our perceptions.
Nothing makes us feel this way; we choose to give in to such feelings.
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
Choose not to be harmed—and you won’t feel harmed. Don’t feel harmed—and you haven’t been. —MARCUS AURELIUS
I am not and never will be powerless.”
declined to surrender the freedoms that were innately his: his attitude, his beliefs, his choices.
This can’t harm me—I might not have wanted it to happen, but I decide how it will affect me. No one else has the right.
We decide what we will make of each and every situation.
Our perceptions are the thing that we’re in complete control of.
they’ll never control our thoughts, our beliefs, our reactions.
we are never completely powerless.
nothing we’ll experience is likely without potential benefit.
“Nothing either good or bad, but thinking makes it so,” as Shakespeare put it.
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.
We decide what story to tell ourselves. Or whether we will tell one at all.
Or try Marcus’s question: Does what happened keep you from acting with justice, generosity, self-control, sanity, prudence, honesty, humility, straightforwardness?
The perceiving eye is weak, he wrote; the observing eye is strong.
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.
The aim was to see these things as they really are, without any of the ornamentation.
Something that’s present when we deal with our own obstacles is always missing when we hear other people’s problems: the baggage. With other people we can be objective.
The more skilled you become seeing things for what they are, the more perception will work for you rather than against you.
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
Perspective is everything.
Fear is debilitating, distracting, tiring, and often irrational.
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.
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.
“business opportunities are like buses; there’s always another coming around.”
Small tweaks can change what once felt like impossible tasks.
“tyranny of being picked.”
Perception precedes action. Right action follows the right perspective.
And what is up to us? Our emotions Our judgments Our creativity Our attitude Our perspective Our desires Our decisions Our determination
What is not up to us? Well, you know, everything else.
When it comes to perception, this is the crucial distinction to make: the difference between the things that are in our power and the things that aren’t.
Focusing exclusively on what is in our power magnifies and enhances our power.
The trick to forgetting the big picture is to look at everything close up. —CHUCK PALAHNIUK
this moment is not your life, it’s just a moment in your life.
Genius is the ability to put into effect what is in your mind. There’s no other definition of it. —F. SCOTT FITZGERALD
This was Jobs’s view of reality at work. Malleable, adamant, self-confident.
He knew that to aim low meant to accept mediocre accomplishment. But a high aim could, if things went right, create something extraordinary.
Our perceptions determine, to an incredibly large degree, what we are and are not capable of.
This is why we shouldn’t listen too closely to what other people say
We’ll find ourselves erring on the side of accomplishing nothing.
An entrepreneur is someone with faith in their ability to make something where there was nothing before.
A good person dyes events with his own color . . . and turns whatever happens to his own benefit. —SENECA
As Laura Ingalls Wilder put it: “There is good in everything, if only we look for it.”
every situation is an opportunity for us to act.
The extent of the struggle determines the extent of the growth.
Action is commonplace, right action is not.
We must be sure to act with deliberation, boldness, and persistence.
Some academic once asked Demosthenes what the three most important traits of speechmaking were. His reply says it all: “Action, Action, Action!”
You’ve got to act. And you’ve got to start now.
It matters what you do with what happens and what you’ve been given.
Because each obstacle we overcome makes us stronger for the next one.
Therefore, we can always (and only) greet our obstacles with energy with persistence with a coherent and deliberate process with iteration and resilience with pragmatism with strategic vision with craftiness and savvy and an eye for opportunity and pivotal moments
We must all either wear out or rust out, every one of us. My choice is to wear out. —THEODORE ROOSEVELT
Because they know that once they get started, if they can just get some momentum, they can make it work.
“Always think with your stick forward.”
Be deliberate, of course, but you always need to be moving forward. And that’s the final part: Stay moving, always.
He says the best way out is always through And I agree to that, or in so far As I can see no way out but through. —ROBERT FROST
We will not be stopped by failure, we will not be rushed or distracted by external noise.
in exhausting all the other traditional options, he’d been forced to try something new.
genius often really is just persistence in disguise.
Persist in your efforts. Resist giving in to distraction, discouragement, or disorder.
It’s okay to be discouraged. It’s not okay to quit.
Stop looking for an epiphany, and start looking for weak points.
What is defeat? Nothing but education; nothing but the first steps to something better. —WENDELL PHILLIPS
Failure really can be an asset if what you’re trying to do is improve, learn, or do something new.
great success are often preceded by epic failure—because
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
Thickheaded and resistant to change, these are the types who are too self-absorbed to realize that the world doesn’t have time to plead, argue, and convince them of their errors.
Lessons come hard only if you’re deaf to them.
Under the comb the tangle and the straight path are the same. —HERACLITUS
That’s the process: Let’s think about what we can do today, the task at hand.”
something very difficult.
break it down into pieces.
do what you need to do right now. And do it well. And then move on to the next thing.
Excellence is a matter of steps.
not getting distracted
The process is about finishing.
Don’t think about the end—think about surviving.
When it comes to our actions, disorder and distraction are death.
Being trapped is just a position, not a fate.
When we know what we’re really setting out to do, the obstacles that arise tend to seem smaller, more manageable. When we don’t, each one looms larger and seems impossible.
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.
When action is our priority, vanity falls away.
if we do our best we can be proud of our choices and confident they’re the right ones.
But duty is beautiful, and inspiring and empowering.
all we need to do is those three little duties—to try hard, to be honest, and to help others and ourselves.
Forget the rule book, settle the issue.
Pragmatism is not so much realism as flexibility.
Start thinking like a radical pragmatist: still ambitious, aggressive, and rooted in ideals, but also imminently practical and guided by the possible.
Think progress, not perfection.
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.
exert only calculated force where it will be effective, rather than straining and struggling with pointless attrition tactics.
You don’t convince people by challenging their longest and most firmly held opinions. You find common ground and work from there.
Wise men are able to make a fitting use even of their enmities. —PLUTARCH
Sometimes you overcome obstacles not by attacking them but by withdrawing and letting them attack you.
Opposites work. Nonaction can be action.
So instead of fighting obstacles, find a means of making them defeat themselves.
Passive resistance is, in fact, incredibly active. But those actions come in the form of discipline, self-control, fearlessness, determination, and grand strategy.
When jarred, unavoidably, by circumstance revert at once to yourself and don’t lose the rhythm more than you can help. You’ll have a better grasp of harmony if you keep going back to it. —MARCUS AURELIUS
But physical looseness combined with mental restraint? That is powerful.
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
paralyzed by fear that they defer taking action.
Their typical response is to hide, ignore, obfuscate, or distance themselves.
“A More Perfect Union” speech, was a transformative moment. Instead of distancing himself, Obama addressed everything directly.
neutralized a potentially fatal controversy but created an opportunity to seize the electoral high ground.
learn how to press forward precisely when everyone around you sees disaster.
act swiftly and unexpectedly to pull off a big victory. While others are arrested by discouragement, we are not.
“You never want a serious crisis to go to waste. Things that we had postponed for too long, that were long-term, are now immediate and must be dealt with. [A] crisis provides the opportunity for us to do things that you could not do before.”
Seize this moment to deploy the plan that has long sat dormant in your head.
turn personal tragedy or misfortune—really anything, everything—to their advantage.
Life speeds on the bold and favors the brave.
Napoleon described war in simple terms: Two armies are two bodies that clash and attempt to frighten each other. At impact, there is a moment of panic and it is that moment that the superior commander turns to his advantage.
It’s the one who rises the next morning after a long day of fighting and rallies,
now—who will carry victory home . . . intelligently.
Nothing can ever prevent us from trying. Ever.
some obstacles may turn out to be impossible to overcome.
turn that obstacle upside down, too, simply by using it as an opportunity to practice some other virtue or skill—even
In every situation, that which blocks our path actually presents a new path with a new part of us.
Sometimes, no amount of planning, no amount of thinking—no matter how hard we try or patiently we persist—will change the fact that some things just aren’t going to work.
Will is our internal power, which can never be affected by the outside world.
Placed in some situation that seems unchangeable and undeniably negative, we can turn it into a learning experience, a humbling experience, a chance to provide comfort to others. That’s will power.
In actuality, the will has a lot more to do with surrender than with strength.
True will is quiet humility, resilience, and flexibility; the other kind of will is weakness disguised by bluster and ambition.
Lincoln suffered periods of intense brooding, isolation, and pain.
He learned to endure all this, articulate it, and find benefit and meaning from it.
Above all, he found purpose and relief in a cause bigger than himself and his personal struggles.
“This too shall pass” was Lincoln’s favorite saying, one he once said was applicable in any and every situation one could encounter.
Leadership requires determination and energy.
If Perception and Action were the disciplines of the mind and the body, then Will is the discipline of the heart and the soul.
Will is fortitude and wisdom—not just about specific obstacles but about life itself
Lincoln learned “to comfort those who suffer too.”
Acknowledge the pain but trod onward in your task.
It’s what allows us to stand undisturbed while others wilt and give in to disorder.
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. And, of course, prepare to start the cycle once more.
If thy faint in the day of adversity, thy strength is small. —PROVERBS 24:10
But he was equipped for it all because of his early training and because he kept at it every single day.
We take weakness for granted.
We assume that the way we’re born is the way we simply are,
They prepare themselves for the hard road.
they are prepared for it
Nobody is born with a steel backbone. We have to forge that ourselves.
(mens sana in corpore sano—sound mind in a strong body).
“In every generation a person is obligated to view himself as if he were the one who went out of Egypt.”
it prompts those partaking in the feast to visualize and possess the strength that has kept them going.
Inner Citadel, that fortress inside of us that no external adversity can ever break down.
we are not born with such a structure; it must be built and actively reinforced.
we should always prepare for things to get tough.
If we’re going to succeed in achieving our goals despite the obstacles that may come, this strength in will must be built.
The path of least resistance is a terrible teacher. We can’t afford to shy away from the things that intimidate us.
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 people don’t have a backup plan because they refuse to consider that something might not go exactly as they wish.
“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.”
sometimes the only answer to “What if . . .” is, It will suck but we’ll be okay.
The only guarantee, ever, is that things will go wrong.
It’s far better to seem like a downer than to be blindsided or caught off guard.
the person who has rehearsed in their mind what could go wrong will not be caught by surprise.
With anticipation, we can endure. We are prepared for failure and ready for success.
The Fates guide the person who accepts them and hinder the person who resists them. —CLEANTHES
It doesn’t always feel that way but constraints in life are a good thing.
They push us to places and to develop skills that we’d otherwise never have pursued.
“True genius,” as the infamous Dr. Samuel Johnson once said, “is a mind of large general powers accidentally determined in some particular direction.”
I can’t just give up! I want to fight!
We can’t argue or yell this problem away. We simply accept it.
When the cause of our problem lies outside of us, we are better for accepting it and moving on.
We instinctively think about how much better we’d like any given situation to be.
We still can’t appreciate what we have.
Follow where the events take you, like water rolling down a hill—it always gets to the bottom
As Francis Bacon once said, nature, in order to be commanded, must be obeyed.
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
To do great things, we need to be able to endure tragedy and setbacks.
We have to learn to find joy in every single thing that happens.
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.
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.
more—letting the opponent dig his own grave.
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 you don’t just want fuel. You need it.
Persistence. Everything directed at one problem, until it breaks.
If persistence is attempting to solve some difficult problem with dogged determination and hammering until the break occurs, then plenty of people can be said to be persistent. But perseverance is something larger. It’s the long game.
round two and every round after—and then the fight after that and the fight after that, until the end.
Life is not about one obstacle, but many.
a determination that we will get to where we need to go, somehow, someway, and nothing will stop us.
Persistence is an action. Perseverance is a matter of will.
This is perseverance. And with it, Emerson said, “with the exercise of self-trust, new powers shall appear.”
Beethoven: “The barriers are not erected which can say to aspiring talents and industry, Thus far and no farther.”
Determination, if you think about it, is invincible.
We don’t control the barriers or the people who put them there. But we control ourselves—and that is sufficient.
The true threat to determination, then, is not what happens to us, but us ourselves.
We’re in this together, he told them. He gave them a watchword to remind them: U.S.—Unity over Self.
But their cause was their men. They cared about their fellow prisoners and drew great strength by putting their well-being ahead of their own.
when we focus on others, on helping them or simply providing a good example, our own personal fears and troubles will diminish.
Shared purpose gives us strength.
one of the best ways to create opportunities or new avenues for movement is to think: If I can’t solve this for myself, how can I at least make this better for other people?
If not for me, then for my family or the others I’m leading or those who might later find themselves in a similar situation.
Start thinking: Unity over Self. We’re in this together.
No harshness, no deprivation, no toil should interfere with our empathy toward others.
Be strong for them, and it will make you stronger.
Death doesn’t make life pointless, but rather purposeful.
embracing the precariousness of our own existence can be exhilarating and empowering.
Remember you are mortal.
We may not say it, but deep down we act and behave like we’re invincible.
What would I change about my life if the doctor told me I had cancer?
Each second, probability is eating away at the chances that we’ll be alive tomorrow;
If something is in our control, it’s worth every ounce of our efforts and energy.
being aware of our mortality creates real perspective and urgency.
Instead of denying—or worse, fearing—our mortality, we can embrace it.
They figure out what they need to do and do it, fitting in as much as possible before the clock expires.
if even our own mortality can have some benefit, how dare you say that you can’t derive value from each and every other kind of obstacle you encounter?
The great law of nature is that it never stops. There is no end. Just when you think you’ve successfully navigated one obstacle, another emerges.
But that’s what keeps life interesting.
that’s what creates opportunities.
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.
Elysium is a myth. One does not overcome an obstacle to enter the land of no obstacles.
the more you accomplish, the more things will stand in your way.
Knowing that life is a marathon and not a sprint is important. Conserve your energy.
Never rattled. Never frantic. Always hustling and acting with creativity.
Simply flipping the obstacles that life throws at you by improving in spite of them, because of them.
They would capture Cassius and endeavor not to kill him, but “. . . forgive a man who has wronged one, to remain a friend to one who has transgressed friendship, to continue faithful to one who has broken faith.”
“settle this affair well and show to all mankind that there is a right way to deal even with civil wars.”
Marcus refused to put any coconspirators to death. He declined to prosecute any of the senators or governors who had endorsed or expressed support for the uprising.
“I implore you, the senate, to keep my reign unstained by the blood of any senator. May it never happen.”
Something stands in someone’s way. They stare it down, they aren’t intimidated. Leaning into their problem or weakness or issue, they give everything they have, mentally and physically. Even though they did not always overcome it in the way they intended or expected, each individual emerged better, stronger.
We can see the “bad” things that happen in our lives with gratitude and not with regret because we turn them from disaster to real benefit—from
First, see clearly. Next, act correctly. Finally, endure and accept the world as it is.
Our actions give us the confidence to ignore or control our perceptions. We prove and support our will with our actions.
There’s a saying in Latin: Vires acquirit eundo (We gather strength as we go).
Like Rockefeller, you’re cool under pressure, immune to insults and abuse. You see opportunity in the darkest of places.
Like Demosthenes, you assume responsibility for yourself—teaching yourself, compensating for disadvantages, and pursuing your rightful calling and place in the world.
Like Lincoln, you realize that life is a trial. It will not be easy, but you are prepared to give it everything you have regardless, ready to endure, persevere, and inspire others.
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.
To be a philosopher is not merely to have subtle thoughts, nor even to found a school . . . it is to solve some of the problems of life, not only theoretically, but practically. —HENRY DAVID THOREAU