The Obstacle is the Way Book Review
The Obstacle is the Way by Ryan Holiday is an introduction to the Stoic disciplines of Perception, Will and Action.
In the author’s words:
This book will share with you their collective wisdom in order to help you accomplish the very specific and increasingly urgent goal we all share: overcoming obstacles. Mental obstacles.
Physical obstacles. Emotional obstacles. Perceived obstacles.
The book is filled with examples of living with guidance of the three Stoic disciplines. It is an easy read and goes past quickly.
Personally I found the book a bit verbose (it is after all a self-help book), but that’s just me. Many will like the detailed explanation and examples.
If you want to understand Stoicism, I recommend your start with Meditations by Marcus Aurelius, The Manual for Living by Epictetus and On the Shortness of Life by Seneca to understand Stoic thought directly from the horses mouth, so to speak.
If you are not planning to read the Stoic classics above, then you can either read my summary of these books (click the links above), or my article on the three disciplines of Stoic Philosophy. Alternatively you may read this book.
The Obstacle is the Way Book Summary
Note: This summary is made up of my notes, thoughts and highlights of important passages while reading the book. I keep updating the summary when I revisit it, and occasionally may edit it to reduce summary length. Don’t be surprised if it has changed between visits. The author’s words are in normal font, while my interpretations are in italics.
INTRODUCTION
The Obstacles That Lie Before Us
“The obstacle in the path becomes the path. Never forget, within every obstacle is an opportunity to improve our condition.”
When you have a goal, obstacles are actually teaching you how to get where you want to go – carving you a path.
“The Things which hurt,” Benjamin Franklin wrote, “instruct.”
Today, most of our obstacles are internal, not external.
The Way Through Them
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
Overcoming obstacles is a discipline of three critical steps.
- It begins with how we look at our specific problems, our attitude or approach;
- then the energy and creativity with which we actively break them down and turn them into opportunities;
- finally, the cultivation and maintenance of an inner will that allows us to handle defeat and difficulty.
It’s three interdependent, interconnected, and fluidly contingent disciplines:
- Perception
- Action
- Will.
Perception
THE DISCIPLINE OF PERCEPTION
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
This is how you see the opportunity within the obstacle.
RECOGNIZE YOUR POWER
Choose not to be harmed – and you won’t feel harmed.
MARCUS AURELIUS
Don’t feel harmed – and you haven’t been.
We decide what we will make of each and every situation.
Through our perception of events, we are complicit in the creation – as well as the destruction – of every one of our obstacles.
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.
STEADY YOUR NERVES
What such a man needs is not courage but nerve control, cool headedness. This he can get only by practice.
THEODORE ROOSEVELT
When we aim high, pressure and stress obligingly come along for the ride.
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.“
This means preparing for the realities of our situation, steadying our nerves so we can throw our best at it.
Steeling ourselves. Shaking off the bad stuff as it happens and soldiering on – staring straight ahead as though nothing has happened.
CONTROL YOUR EMOTIONS
Would you have a great empire?
PUBLIUS SYRUS
Rule over yourself.
Uncertainty and fear are relieved by authority. Training is authority.
Life is really no different. Obstacles make us emotional, but the only way we’ll survive or overcome them is by keeping those emotions in check.
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.
You can always remind yourself: I am in control, not my emotions. I see what’s really going on here. I’m not going to get excited or upset.
PRACTICE OBJECTIVITY
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
The phrase “This happened and it is bad” is actually two impressions.
- The first – “This happened” – is objective.
The second – “it is bad” – is subjective.
The observing eye sees simply what is there. The perceiving eye sees more than what is there.
ALTER YOUR PERSPECTIVE
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
Richard Branson likes to say, is that “business opportunities are like buses; there’s always another coming around.”
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.
How we interpret the events in our lives, our perspective, is the framework for our forthcoming response.
Where the head goes, the body follows.
Perception precedes action.
Right action follows the right perspective.
IS IT UP TO YOU?
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
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.
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.
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.
The weather, the economy, circumstances, other people’s emotions or judgments, trends, disasters, et cetera.
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.
Every ounce of energy directed at things we can’t actually influence is wasted – self-indulgent and self-destructive.
LIVE IN THE PRESENT MOMENT
The trick to forgetting the big picture is to look at everything close up.
CHUCK PALAHNIUK
Run down the list of businesses started during depressions or economic crises.
These businesses had little awareness they were in some historically significant depression. Why? Because the founders were too busy existing in the present – actually dealing with the situation at hand.
Half the companies in the Fortune 500 were started during a bear market or recession.
Focus on the moment, not the monsters that may or may not be up ahead.
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.
THINK DIFFERENTLY
Genius is the ability to put into effect what is in your mind. There’s no other definition of it.
F. SCOTT FITZGERALD
FINDING THE OPPORTUNITY
A good person dyes events with his own color and turns whatever happens to his own benefit.
SENECA
“There is good in everything, if only we look for it.”
Blessings and burdens are not mutually exclusive.
The struggle against an obstacle inevitably propels the fighter to a new level of functioning. The extent of the struggle determines the extent of the growth.
PREPARE TO ACT
Then imitate the action of the tiger; stiffen the sinews, summon up the blood.
SHAKESPEARE
PART II PREFACE WHAT IS ACTION?
THE DISCIPLINE OF ACTION
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.
GET MOVING
We must all either wear out or rust out, every one of us. My choice is to wear out.
THEODORE ROOSEVELT
If you want momentum, you’ll have to create it yourself, right now, by getting up and getting started.
PRACTICE PERSISTENCE
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
Persist in your efforts. Resist giving in to distraction, discouragement, or disorder.
Energy is an asset we can always find more of. It’s a renewable resource.
ITERATE
What is defeat? Nothing but education; nothing but the first steps to something better.
WENDELL PHILLIPS
Failure is a Feature.
Failure really can be an asset if what you’re trying to do is improve, learn, or do something new. It’s the preceding feature of nearly all successes.
Action and failure are two sides of the same coin.
People fail in small ways all the time. But they don’t learn.
It’s time you understand that the world is telling you something with each and every failure and action. It’s feedback.
Failure shows us the way – by showing us what isn’t the way.
FOLLOW THE PROCESS
Under the comb the tangle and the straight path are the same.
HERACLITUS
The process is about finishing. Finishing games. Finishing workouts.
Being trapped is just a position, not a fate.
The process is the voice that demands we take responsibility and ownership. That prompts us to act even if only in a small way.
DO YOUR JOB, DO IT RIGHT
Whatever is rightly done, however humble, is noble. (Quidvis recte factum quamvis humile praeclarum.)
SIR HENRY ROYCE
To whatever we face, our job is to respond with: hard work honesty helping others as best we can.
WHAT’S RIGHT IS WHAT WORKS
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
Forget the rule book, settle the issue.
Don’t worry about the “right” way, worry about the right way. This is how we get things done.
Pragmatism is not so much realism as flexibility.
Deng Xiaoping once said, “I don’t care if the cat is black or white, so long as it catches mice.”
IN PRAISE OF THE FLANK ATTACK
Whoever cannot seek the unforeseen sees nothing, for the known way is an impasse.
HERACLITUS
“Where little danger is apprehended, the more the enemy will be unprepared and consequently there is the fairest prospect of success.”
Remember, sometimes the longest way around is the shortest way home.
USE OBSTACLES AGAINST THEMSELVES
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. You can use the actions of others against themselves instead of acting yourself.
CHANNEL YOUR ENERGY
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
SEIZE THE OFFENSIVE
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
“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.”
PREPARE FOR NONE OF IT TO WORK
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
Perceptions can be managed. Actions can be directed.
In every situation, that which blocks our path actually presents a new path with a new part of us.
PART III Will
WHAT IS WILL?
Will is our internal power, which can never be affected by the outside world.
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.
We must prepare for adversity and turmoil, we must learn the art of acquiescence and practice cheerfulness even in dark times.
THE DISCIPLINE OF THE WILL
As crafty and ambitious and smart as he was, Lincoln’s real strength was his will: the way he was able to resign himself to an onerous task without giving in to hopelessness, the way he could contain both humor and deadly seriousness, the way he could use his own private turmoil to teach and help others, the way he was able to rise above the din and see politics philosophically. “This too shall pass” was Lincoln’s favorite saying,
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 and where the obstacles we are facing fit within it.
The Stoic maxim: sustine et abstine. Bear and forbear. Acknowledge the pain but trod onward in your task.
It’s much easier to control our perceptions and emotions than it is to give up our desire to control other people and events.
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.
BUILD YOUR INNER CITADEL
Nobody is born with a steel backbone. We have to forge that ourselves.
ANTICIPATION (THINKING NEGATIVELY)
Offer a guarantee and disaster threatens.
ANCIENT INSCRIPTION AT THE ORACLE OF DELPHI
“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.”
The only guarantee, ever, is that things will go wrong. The only thing we can use to mitigate this is anticipation. Because the only variable we control completely is ourselves.
With anticipation, we can endure. We are prepared for failure and ready for success.
THE ART OF ACQUIESCENCE
The Fates guide the person who accepts them and hinder the person who resists them.
CLEANTHES
The ancients (and the not so ancients) used the word fate far more frequently than us because they were better acquainted with and exposed to how capricious and random the world could be.
Francis Bacon once said, nature, in order to be commanded, must be obeyed.
LOVE EVERYTHING THAT HAPPENS: AMORFATI
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
We don’t get to choose what happens to us, but we can always choose how we feel about it.
PERSEVERANCE
Gentleman, I am hardening on this enterprise. I repeat, I am now hardening towards this enterprise.
WINSTON CHURCHILL
Persistence is an action. Perseverance is a matter of will. One is energy. The other, endurance.
Our actions can be constrained, but our will can’t be.
SOMETHING BIGGER THAN YOURSELF
A man’s job is to make the world a better place to live in, so far as he is able – always remembering the results will be infinitesimal – and to attend to his own soul.
LEROY PERCY
The desire to quit or compromise on principles suddenly feels rather selfish when we consider the people who would be affected by that decision.
MEDITATE ON YOUR MORTALITY
When a man knows he is to be hanged in a fortnight, it concentrates his mind wonderfully.
DR. JOHNSON
Death doesn’t make life pointless, but rather purposeful.
PREPARE TO START AGAIN
Live on in your blessings, your destiny’s been won. But ours calls us on from one ordeal to the next.
VIRGIL
Haitian proverb puts it: Behind mountains are more mountains.
FINAL THOUGHTS – The Obstacle Becomes the Way
Writing in his journal, Marcus once reminded himself that “when the fire is strong, it soon appropriates to itself the matter which is heaped on it, and consumes it, and rises higher by means of this very material.“
Nassim Nicholas Taleb defined a Stoic as someone who “transforms fear into prudence, pain into transformation, mistakes into initiation and desire into undertaking.”
Remind ourselves:
- 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.
POSTSCRIPT
You’re Now a Philosopher. Congratulations.
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
The essence of philosophy is action.
Philosophy was never what happened in the classroom. It was a set of lessons from the battlefield of life.
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.
Now you are a philosopher and a person of action. And that is not a contradiction.
THE STOIC READING LIST
Stoicism is perhaps the only “philosophy” where the original, primary texts are actually cleaner and easier to read than anything academics have written afterward.
- Meditations by Marcus Aurelius (Modern Library).
- Letters of a Stoic by Seneca (see also: On the Shortness of Life).
- Discourses by Epictetus (Penguin).
- Philosophy as a Way of Life explains how philosophy has been wrongly interpreted as a thing people talk about rather than something that people do.
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