The Obstacle Is The Way by Ryan Holiday - Book Summary

3 Sentence Summary

Nobody has perhaps had a greater influence on popularizing the teachings of Marcus Aurelius and stoic philosophy than Ryan Holiday. This book quickly became a cult classic as inspiration to perform our best by using obstacles as opportunities to get better, stronger, and tougher. To let go of what you can’t control and focus on what you can is the driving message behind this a book that will motivate you to accept challenges head-on as the best path to success.

5 Key Takeaways

Get the right perspective. See things for what they are.
Take action. Do what you can with what you have.
Endure and bear what you must. Be persistent.
Don’t be a victim. Focus on what you can control.
Learn to view obstacles as welcomed opportunities.

The Obstacle Is The Way Summary

Please Note

The following book summary is a collection of my notes and highlights taken straight from the book. Most of them are direct quotes. Some are paraphrases. Very few are my own words.

These notes are informal. I try to organize them by chapter. But I pick and choose ideas to include at my discretion.

Enjoy!

Preface / Introduction

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 actions. What stands in the way becomes the way.
Marcus Aurelius

Every obstacle is an opportunity to practice some virtue: patience, courage, humility, resourcefulness, reason, justice, or creativity.
Whatever we face, we have a choice: Will we be blocked by obstacles, or will we advance through and over them?
Every obstacle is unique to each of us. But the responses they elicit are the same: Fear. Frustration. Confusion. Helplessness. Depression. Anger.
Instead of succumbing to obstacles with inaction, we need a method and a framework for understanding, appreciating, and acting upon the obstacles life throws at us.
Great individuals, like great companies, find a way to transform weakness into strength.
Like oxygen to a fire, obstacles became fuel for the blaze that was their ambition.
Many of our problems come from having too much. We’re soft, entitled, and scared of conflict.
Great times are great softeners. Abundance can be its own obstacle.

The Discipline of Perception

Be fearful when others are greedy and greedy when others are fearful.
Warren Buffet

What matters most is not what the obstacle is, but how you see and react to them.
Nothing makes us feel this way; we choose to (or not to) give in to such feelings.
We can choose to stop seeing the “problems” in front of us as problems. We can learn to focus on what things really are.
Too often we react emotionally, get despondent, and lose our perspective.
Discipline in perception lets you clearly see the advantage and the proper course of action in every situation—without the pestilence of panic or fear.

How to Keep Your Perspective

Be objective
Control your emotions and keep an even keel
Choose to see the good in the situation
Steady your nerves
Ignore what disturbs or limits others
Place things in perspective
Revert to the present moment
Focus on what can be controlled

Recognize Your Power

Choose not to be harmed—and you won’t feel harmed. Don’t feel harmed—and you haven’t been.
Marcus Aurelius

We decide what we will make of each and every situation.
We are never completely powerless.
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.
Just because other people say that something is hopeless or crazy or broken to pieces doesn’t mean it is.
Nobody can take away your ability to choose what story you tell yourself.

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.
Grace and poise are the two attributes that precede the opportunity to deploy any other skill.
There is always a countermove, always an escape or a way through, so there is no reason to get worked up. No one said it would be easy and, of course, the stakes are high, but the path is there for those ready to take it.

Control Your Emotions

Would you have a great empire? Rule over yourself.
Publius Syrus

We crave panic because it’s easier than dealing with whatever is staring us in the face.
Uncertainty and fear are relieved by authority. Training is authority.
Unfamiliarity is simple to fix which makes it possible to increase our tolerance for stress and uncertainty.
Apatheai = The kind of calm equanimity that comes with the absence of irrational or extreme emotions.
You can’t afford to panic.
This is the skill that must be cultivated—freedom from disturbance and perturbation—so you can focus your energy exclusively on solving problems, rather than reacting to them.
Does getting upset provide you with more options? (Usually not)
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.
Real strength lies in the control, or the domestication of one’s emotions, not in pretending they don’t exist.
Don’t conflate emoting about a problem and dealing with it. They are as different as sleeping and waking.
Sometimes its worth repeating to yourself: I am not going to die from this. I am not going to die from this…
Or try asking: Does what happened keep me from acting with justice, generosity, self-control, sanity, prudence, honesty, humility, straightforwardness? If the answer is “no,” get back to work!

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

In our own lives, how many problems seem to come from applying judgements to things we don’t control, as though there were a way they were supposed to be?
How often do we see what we think is there or should be there, instead of what actually is there?
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.
See things as they really are, without any of the ornamentation.
Objectivity means removing “you”—the subjective part—from the equation.
Take your situation and pretend it is not happening to you. Pretend it is not important, that it doesn’t matter. How much easier would it be for you to know what to do?

Alter Your Perspective

Man does not simply exist but always decides what his existences 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

Fear is debilitating, distracting, tiring, and often irrational. Use the power of perspective to defeat it.
We often choose the ominous explanation over the simple one, to our detriment.
Do not ignore fear, but explain it away.
The right perspective has a strange way of cutting obstacles and adversity down to size.
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

Focusing exclusively on what is in our power magnifies and enhances our power.
To argue, to complain, or to give up are all choices.
Perception gives you the ability to differentiate between things that are and are not within your control. That’s the difference between people who can accomplish great things and those that find it impossible.

Things Always Within Your Control

Your emotions
Your judgments
Your creativity
Your attitude
Your perspective
Your desires
Your decisions
Your determination

Live In The Present Moment

The trick to forgetting the big picture is to look at everything close up.
Chuck Palahniuk

We 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.
Most people start from disadvantage (often with no idea they are doing so) and do just fine. It’s not unfair, it’s universal.
Focus on the moment, no the monsters that may or may not be up ahead.
You have to work on living in the present. Find a method that works for you: Exercise. Unplugging. Going for a walk. Mediation.
Discard distracting thoughts. Leave things well enough alone—no matter how much you feel like doing otherwise.
This moment is not your life, it’s just a moment in your life.

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

So many people in our lives have preached the need to be realistic or conservative or worse—to not rock the boat. This is an enormous disadvantage when it come to trying big things.
Our perceptions determine, to an incredibly large degree, what we are and are not capable of.
Don’t believe in the obstacle more than the goal.
Don’t listen too closely to what other people say (or to what the voice in our head says, either). Otherwise you’ll find yourself erring on the side of accomplishing nothing.
Steve Jobs learned to reject the first judgments and the objections that spring out of them because those objections are almost always rooted in fear.
When given an unfair task, some rightly see it as a chance to test what they’re made of. Our best ideas come from there, where obstacles illuminate new options.

Finding The Opportunity

A good person dyes events with his own color…and turns whatever happens to his own benefit.
Seneca

Our preconceptions are the problem. They tell us tat 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.
Blessings and burdens are not mutually exclusive.
“That which doesn’t kill me makes me stronger” is not a cliché but fact.
The obstacle is an advantage, not adversity.

Prepare To Act

Then imitate the action of the tiger; stiffen the sinews, summon up the blood.
Shakespeare

Problems are rarely as bad as we think—or rather, they are precisely as bad as we think.
The worst thing to happen is never the event, but the event and losing your head.
A clearer head makes for steadier hands.
We all have to make assumptions in life, we have to weigh the costs and benefits.
Boldness is acting anyway, even though you understand the negative and the reality of your obstacle.

The Discipline of Action

When you’re dealt a bad hand, what’s your response? Do you fold? Or do you play it for all you’ve got?
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.
No one is coming to save you. It’s up to you.

Greet Obstacles With…

Energy
Persistence
A coherent and deliberate process
Iteration and resilience
Pragmatism
Strategic vision
Craftiness and savvy
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

That’s what people who become great at things—whether it’s flying or blowing through gender stereotypes—do. They start. Anywhere. Anyhow.
Step 1: Take the bat off your shoulder and take a swing.
Do more. Try harder. Give it your full effort.
Step 2: Ram your feet into the stirrups and really go for it.
Don’t let yourself go soft. Stay aggressive. Press ahead relentlessly.
Step 3: Stay moving, always.
Those that attack problems and life with the most initiative and energy usually win.
Just because the conditions aren’t exactly to your liking, or you don’t feel ready yet, doesn’t mean you get a pass. 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

We will not be stopped by failure, we will not be rushed or distracted by external noise. We will chisel and peg away at the obstacle until it is gone. Resistance is futile.
Persistence is how innovation works.
Genius often really is just persistence in disguise.
Working at it works. It’s that simple.
Do you have the patience to refine your ideas? The energy to beat on enough doors until you find investors or supporters?
Once you start attacking an obstacle, quitting is not an option.
Persist and resist. Persist in your efforts. Resist giving in to distraction, discouragement, or disorder.
It’s okay to feel discouraged. It’s not okay to quit.
It’s supposed to be hard. your first attempts aren’t going to work.
Stop looking for an epiphany, and start looking for weak points.

The Persistence Mindset

Never in a hurry
Never worried
Never desperate
Never stopping short

Iterate

What is defeat? Nothing but education; nothing but the first steps to something better.
Wendell Phillips

View yourself as a start-up—a start-up of one.
Your capacity to try, try, try is inextricably linked with your ability and tolerance to fail, fail, fail.
Action and failure are two sides of the same coin.
When failure does come, ask: What went wrong here? What can be improved? What am I missing?
Failure is a source of breakthroughs.
Stories of great success are often preceded by epic failure.
The one way to guarantee we don’t benefit from failure is to not learn from it.
Failure shows us the way—by showing us what isn’t the way.

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

Follow the Process

Under the comb
the tangle and the straight path
are the same.
Heraclitus

Don’t focus on the difficult task ahead. Break it down into pieces. Simply do what you need to do right now.
The process is about finishing. Finishing the smallest task in front of you and finishing it well.
The unordered mind loses track of what’s in front of it—what matters—and gets distracted by thoughts of the future.
Replace fear with the process. Depend on it. Lean on it. Trust in it.

Do Your Job, Do It Right

Whatever is rightly done, however humble, is noble.
Sir Henry Royce

Sometimes, on the road to where we are going or where we want to be, we have to do things we’d rather not do. But there’s nothing shameful about sweeping. It’s just another opportunity to excel—and to learn.
Everything we do matters. Everything is a chance to do and be your best.
Only self-absorbed assholes think they are too good for whatever their current station requires.
When action is our priority, vanity falls away.
Duty is beautiful, and inspiring and empowering.
All we need to do is try hard, be honest, and help others and ourselves.

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

Embody pragmatism.
Don’t worry about he “right” way, worry about the right way. This is how we get things done.
Any way that works—that’s the motto.
Focus on results. Don’t belabor pretty methods.
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.
Don’t think small, but make the distinction between the critical and the extra.
Think progress, not perfection.

In Praise Of The Flank Attack

Whoever cannot seek
the unforeseen sees nothing,
for the known way
is an impasse.
Heraclitus

Find victory in the flanks, from the unexpected, from the untraditional.
Go around the problem. Find some leverage. Approach from what is called the “line of least expectation.”
Don’t try to barge through the font door when the back door and side windows may have been left wide open.
Exert calculated force where it will be effective instead of straining and struggling with pointless attrition tactics.
Obstacles force us to be creative, to find workarounds, to sublimate the ego and do anything to win besides challenging our enemies where they are strongest.
You don’t convince people by challenging their longest and most firmly held opinions. You find common ground and work from there.
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, instead of fighting obstacles, you need to find a means of making them defeat themselves.
Be ready to see that restraint might be the best action for you to take.
It doesn’t naturally occur to use that standing still—or in some cases, even going backward—might be the best way to advance.
A castle can be an intimidating, impenetrable fortress, or it can be turned into a prison when surrounded. The difference is simply a shift in action and approach.

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.
Marcu Aurelius

Adversity can harden you. Or it can loosen you up and make you better—if you let it.
While others obsess with observing the rules, you can subtly undermine them and subvert them to your advantage.
External factor influence the path, but not the direction: forward.
Physical looseness combined with mental restraint is powerful.

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

If you think it’s simply enough to take advantage of the opportunities that arise in your life, you will fall short of greatness. Anyone sentient can do that. What you must do is learn how to press forward precisely when everyone around you sees disaster.
Never let a crisis go to waste. A crisis provides an opportunity to do things that could not be done before.
Great people turn misfortune into their advantage.

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

You cannot control the world around you. But nothing can ever prevent you from trying.
In every situation, that which blocks your path actually presents a new path with a new part of you.
If there is nothing else you can do for yourself, at least you can try to help others.
Be prepared to roll the dice and lose.
We have it within us to be the type of people who try to get things done, try with everything we’ve got and, whatever verdict comes in, are ready to accept it instantly and move on to whatever is next.

The Discipline Of The Will

Leadership requires determination and energy.
Sometimes we just need the energy to endure.
Will is the discipline of the heart and the soul.
Will can be controlled completely, always.
Bear and forbear. Acknowledge the pain but trod onward in your task.

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

If they faint in the day of adversity, thy strength is small.
Proverbs 24:10

Nobody is born with a steel backbone. We have to forge that ourselves.
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.
Always prepare for things to get tough.
The way to strengthen an arch is to put weight on it—because it binds the stones together, and only with tension does it hold weight.
The path of least resistance is a terrible teacher. We can’t afford to shy away from the things that intimidate us.

Anticipation (Thinking Negatively)

Offer a guarantee and disaster threatens.
Ancient Inscription at the Oracle of Delphi

Premortem = An exercise in envisioning what could go wrong, what will go wrong, in advance, before you start.
In the case where nothing can be done, it’s important to manage expectations. It will suck, but we will be okay.
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.

The Art of Acquiescence

The Fates guide the person who accepts them and hinder the person who resists them.
Cleanthes

Constraints in life are a good thing. Especially if we can accept them and let them direct us. They push us to places and to develop skills that we’d otherwise never have pursued.
You don’t have to like something to master it—or use it to some advantage.
We instinctively think about how much better we’d like any given situation to be. We start thinking about what we’d rather have. Rarely do we consider how much worse things could have been.
Appreciate what you have.
Be humble and flexible enough to acknowledge that there is always someone or something that could change the plan.

Love Everything That Happens: Amor Fati

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’ve got to love what we do and all that it entails, good and bad. We have to learn to find joy in every single thing that happens.
Turn what you must do into what you get to do.
Wear down your obstacles with a relentless smile.
Don’t waste a second looking back at your expectations. Face forward, and face it with a smug little grin.

Perseverance

Gentleman, I am hardening on this enterprise. I repeat, I am now hardening towards this enterprise.
Winston Churchill

Life is not about one obstacle, but many. You need determination that you will get to where you need to go, somehow, someway, and nothing will stop you.
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. Our plans—even our bodies—can be broken. But not our belief in ourselves.
Determination is invincible.

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

By focusing on helping others, or simply providing a good example, our own personal fears and troubles will diminish.
Shared purpose gives us strength.
Stop thinking only of yourself. If you can’t help yourself, help others.
Unity over Self. We’re in this together.
Compassion and camaraderie are always an option.
Stop pretending that what you’re going through is somehow special or unfair. Whatever trouble you’re having—no matter how difficult—is not some unique misfortune picked out especially for you. It just is what it is.
Embrace being part of a much larger whole. You are just a brief moment in history.

Meditate On Your Mortality

When a man knows he is to be hanged in a fortnight, it concentrates his mind wonderfully.
Dr. Johnson

Embracing the precariousness of our own existence can be exhilarating and empowering.
We all have a death sentence. So what are you doing with your life until then? What truly matters?
Thinking about and being aware of our mortality creates real perspective and urgency.
In the shadow of death, prioritization is easier. As are graciousness and appreciation and principles.

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

The more you accomplish, the more things will stand in your way.
Life is a marathon, not a sprint. Conserve your energy. Keep everything in long-term perspective.

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