“The Obstacle Is the Way” by Ryan Holiday (Book Summary)

The Obstacle Is the Way by Ryan Holiday is a book that reframes a forgotten formula for success: “What stands in the way becomes the way.”

He shares countless stories of great men and women who succeeded in their lives because they lived by this formula. Holiday says, “Whatever we face, we have a choice: Will we be blocked by obstacles, or will we advance through and over them?”

The book is about mindsets that help us face adversity effectively. It teaches us how to master our emotions, how to build emotional resilience, develop persistence, and how to resist what’s so hard to resist. It helps us live in the present moment and to accept reality as it is, and yet not to resign but always try our very best.

How can we use the challenges we’re facing in life as opportunities for growth? The mindsets in this book are for anyone who’s eager to move ahead and become a better person.

Who is The Obstacle Is the Way for?

• Anyone who’s struggling to get off their butt and take action
• Anyone interested in practical mindsets to deal with life’s struggles
• Anyone who needs to better control their emotions

1. The Basic Idea of The Obstacle Is the Way

What he [Marcus Aurelius] wrote is undoubtedly one of history’s most effective formulas for overcoming every negative situation we may encounter in life. A formula for thriving not just in spite of whatever happens but because of it.

In Marcus’ words is the secret to an art known as turning obstacles upside down:

“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.”

This idea from Marcus Aurelius, that every obstacle presents an opportunity for growth, is what The Obstacle Is the Way is based on. Accepting challenging situations will make you better than if you’d never faced the adversity at all.

The outcomes of your actions can be impeded, but never your good intentions. Every obstacle offers an opportunity to practice virtue: “patience, courage, humility, resourcefulness, reason, justice, and creativity.”

2. The Problem: We’re Dissatisfied but Do Nothing

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

How skilled we are at cataloging what holds us back!

You know what you want to do but it feels like some invisible enemy has you boxed in, holding you down with pillows.

We’re dissatisfied with our jobs, relationships, our place in the world. We’re trying to get somewhere, but something stands in the way. So we do nothing.

We blame our bosses, the economy, our politicians, other people, or we write ourselves off as failures or our goals as impossible. When really only one thing is at fault: our attitude and approach.

What are we missing? It’s simple: a method and a framework for understanding, appreciating, and acting upon the obstacles life throws at us.

You know what you want to do but some invisible force is holding you back. That’s when many of us do nothing, because we’re lacking a framework that helps us face and deal with our challenges.

Holiday offers a framework.

3. The Three Disciplines of the Framework

Our generation needs an approach for overcoming obstacles and thriving amid chaos more than ever. One that will help turn our problems on their heads, using them as canvases on which to paint master works.

Overcoming obstacles is a discipline of three critical steps:

Perception is how we see and understand what occurs around us – and what we decide those events will mean. Our perceptions can be a source of strength or of great weakness… While others are excited or afraid, we will remain calm and imperturbable.

Action is commonplace, right action is not. As a discipline, it’s not any kind of action that will do, but directed action… With persistence and flexibility, we’ll act in the best interest of our goals… We must be sure to act with deliberation, boldness, and persistence.

Will is our internal power, which can never be affected by the outside world. It is our final trump card… Too often people think that will is how bad we want something. In actuality, the will has a lot more to do with surrender than with strength… True will is quiet humility, resilience, and flexibility.

To turn obstacles into opportunities, we need three things: (1) Objective judgment when we look at our specific problems, (2) unselfish action to break them down into opportunities, and (3) the cultivation of an inner will that allows us to handle defeat and difficulty.

4. The Discipline of Perception

You will come across obstacles in life – fair or 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.

Where one person sees a crisis, another can see opportunity.

Outward appearances are deceptive. What’s within them, beneath them, is what matters.

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.

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

Holiday explains that there are a few things to keep in mind when faced with an obstacle. We must try to be objective, control our emotions, place things in perspective, stay in the present moment, and, most importantly, focus on what can be controlled.

5. Domesticate Your Emotions

Welcome to the source of most or our problems down here on Earth. Everything is planned down to the letter, then something goes wrong and the first thing we do is trade in our plan for a good ol’ emotional freak-out.

Obstacles make us emotional, but the only way we’ll survive or overcome them is by keeping those emotions in check – if we can keep steady no matter what happens.

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, as Nassim Taleb put it, the domestication of one’s emotions, not in pretending they don’t exist.

The idea is to defeat emotions with logic – with questions and statements.

Do I need to freak out about this? – No, because I practiced for this situation and I can control myself.

We need to be able to spot our initial impressions and then ask whether this is helpful or not. Whether we control it or not. And whether what happened must keep ourselves from acting with justice, forgiveness, and self-control.

If not, then let’s get back to work.

6. The Discipline of Action

We’ve all done it. Said: “I am so [overwhelmed, tired, stressed, busy, blocked, outmatched].” And then what do we do about it? Go out and party. Or treat ourselves. Or sleep in. Or wait.
It feels better to ignore or pretend. But you know deep down that that isn’t going to truly make it any better. You’ve got to act. And you’ve got to start now.

We forget: In life, it doesn’t matter what happens to you or where you came from. It matters what you do with what happens and what you’ve been given. And the only way you’ll do something spectacular is by using it all to your advantage.

People turn shit into sugar all the time – shit that’s a lot worse than whatever we’re dealing with.

No one is coming to save you. And if we’d like to go where we claim we want to go – to accomplish what we claim are our goals – there is inly one way. And that’s to meet our problems with the right action.

If we’re not happy with where we are, we need to take action. It’s up to us, no one is coming to save us. According to Holiday, everything we do matters and everything is a chance to do and be our best.

All that’s been asked of us is to try hard, to be honest, and to help others and ourselves.

7. Persist and You Will Succeed

If we’re to overcome our obstacles, this is the message to broadcast – internally and externally. 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.

Remember and remind yourself of a phrase by Epictetus: “persist and resist.” Persist in your efforts. Resist in giving in to distraction, discouragement, or disorder.

You’re in this for the long haul. Because when you play all the way to the whistle, there’s no reason to worry about the clock. You know you won’t stop until it’s over.

Only by persisting and resisting can we learn what others were too impatient to be taught.

Stop looking for angels, and start looking for angles. There are options. Settle in for the long haul and then try each and every possibility, and you’ll get there.

Hard and persistent work will pay off. “It’s okay to be discouraged,” says Holiday. But “it’s not okay to quit.” Play the long game. Never give up. Keep on working towards your goal. Determination is invincible.

8. Prepare for None of It to Work

Perceptions can be managed. Actions can be directed. We can always think clearly, respond creatively… What we can’t do is control the world around us – not as much as we’d like to, anyway. We might perceive things well, ten act rightly, and fail anyway.

Run it through your head like this: Nothing can ever prevent us from trying. Ever.

It’s an infinitely elastic formula: In every situation, that which blocks our path actually presents a new path with a new part of us. If someone you love hurts you, there is a chance to practice forgiveness. If your business fails, now you can practice acceptance.

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, are ready to accept it instantly and move on to whatever is next.

We must be willing to roll the dice and lose. Prepare, at the end of the day, for none of it to work.

We can try hard and persist, but this won’t change the fact that not everything is going to work out as planned. We need to prepare to deal effectively with such setbacks.

That’s where true will enters the game.

9. The Discipline of Will

The will is the critical third discipline. We can think, act, and finally adjust to a world that is inherently unpredictable. The will is what prepares us for this, protects us against it, and allows us to thrive and be happy in spite of it.

It’s what allows us to stand undisturbed while others wilt and give in to disorder. Confident, calm, ready to work regardless of the conditions. Willing and able to continue, even during the unthinkable, even when our worst nightmares have come true.

No one is born a gladiator… If we’re going to succeed in achieving our goals despite the obstacles that may come, this strength in will must be built. To be great at something takes practice.

There are things we can’t change. Sometimes we need to discard our expectations and accept what happens around us. Certain things are outside your control and you’ve got only one option: acceptance.

Holiday shares the inspiring story of the great boxer Jack Johnson: His famous fifteen-round brawl with Jim Jeffries. Jeffries, the Great White Hope, called out of retirement to defeat the ascendant black champion. And Johnson, genuinely hated by his opponent and the crowd, still enjoying every minute of it. Smiling, joking, playing the whole fight.

Johnson kept his cool and was even enjoying this fight despite all the hate and nasty remarks. And we can do the same in far less brutal circumstances: Stay calm, always in control, and loving the opportunity to prove yourself and be your best.

10. Behind Mountains Are More Mountains

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.

Life is a process of breaking through these impediments – a series of fortified lines that we must break through.

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.

As the Haitian proverb puts it: Behind mountains are more mountains. Elysium is a myth. One does not overcome an obstacle to enter the land of no obstacles.

On the contrary, the more you accomplish, the more things will stand in your way… You’re always fighting uphill. Get used to it and train accordingly.

Never rattled. Never frantic. Always hustling and acting with creativity. Never anything but deliberate. Never attempting to do the impossible – but everything up to that line.

Life is supposed to be hard. It’s how we grow. Viktor Frankl once spoke one of my favorite line:

“What is to give light must endure burning.”

In that sense. Let’s keep trying our best, day-in, day-out.

The last words belong to Ryan Holiday who shared this Latin saying: Vires acquirit eundo (We gather strength as we go).