Book Name

The Obstacle is the Way by Ryan Holiday



One Line Summary

What stands in the way becomes the way

The Setup

In my review of the Mediations by Marcus Aurelius, I touched on this idea of flipping your perspective on obstacles. But Ryan Holiday has really took this concept and run with it in The Obstacle is the Way.

If you don’t know Ryan Holiday, he’s a young entrepreneur and author. He’s tough to classify because he has positioned himself in a lot of different domains. My guess is that he would think of himself like a modern day philosopher.

I really enjoy his books. He has some other good ones called Trust Me, I’m Lying and Ego is the Enemy that hopefully I’ll get to reviewing at some point. But I still think The Obstacle is the Way is my favorite.

So what’s this book about? Well the subtitle is “the classic art of turning trials into triumph”. That’s a pretty spot on description.

People who are highly effective executors in life have this seemingly magical ability to take obstacles and not only succeed in spite of them, but actually because of them. They take obstacles and almost use them like a ladder to get to the next level.

Not only does this make them effective executors, but think of the psychological quality of life that kind of person might have. How would you feel if EVERYTHING was moving you towards your goals, even obstacles?

You’d be relaxed. At ease. You may even have a feeling of support by nature or God, because it’s like everything is just working out in perfection.

Now compare that to how the average person looks at obstacles. Complain, whine, make excuses, get depressed, feel angry etc.

Of course everyone probably has been a bit of both at times. I know I have. And I’m not looking down at people who behave that way because I get it. Life can seem tough as shit, if not downright impossible.

But if you’re here, I’m going to assume that’s not what you want. You want to move towards the first category of people. You want to be an executor.


Keep reading.

Why it’s Awesome

Although the book title is a reference to Marcus Aurelius, this concept of the obstacle is the way is not just a Stoic ideal. Holiday is constantly referencing people throughout history from all different cultures and backgrounds who have embodied this and giving examples of their triumphs.

Part of the reason I like this book is because unfortunately I don’t read much history, and Holiday is a history buff. So he gave me some new perspectives I wasn’t familiar with.

Some of the people he uses as examples include Abraham Lincoln, John D Rockefeller and Thomas Edison. These are all people who lived this philosophy of the obstacle is the way, even if they didn’t know it.

So how do we turn trials into triumph?

Holiday breaks it down into 3 separate parts. They are:

  • Perception
  • Action
  • Will

Let’s go though each individually.


The first point Holiday makes is that it’s about perception. You don’t have to put your head in the sand and pretend there isn’t an obstacle with “positive-thinking”. There is an obstacle. But it’s your perception of how to look at this obstacle that will make the difference.

The perception you want to have in this case is one of acceptance. Even if you prefer there wouldn’t be an obstacle, you’re excepting that this is what life has given to you in the present moment and it can’t be any other way. Anything but acceptance is essentially insanity.

Acceptance also doesn’t mean a suppression of emotions. But at some point you do have deal with your situation as it is.

So it’s a non-resistance to life and the things we can’t control.

Holiday doesn’t go into this in the book, but many westerners hate this idea of non-resistance because it’s very scary to feel like we’re not in control. We’re very identified with the “poor little me” as Alan Watts calls it.

This “poor little me” sees the outside world as fundamentally unintelligent, mechanical and hostile. And so if we don’t step in, take control and protect ourselves, who knows what might happen?

But that’s not the way other cultures have viewed reality for thousands of years.

Every major religion, at its core at least, understands this truth that actually you are not just in the world. You are the whole world. Just like how a drop of water is simultaneously the whole ocean. It’s all One thing, and the need to defend yourself is mostly an illusion.

Let’s look at the ancient Yin Yang symbol. The Yin Yang symbol is a reminder that opposites are actually One. And not only do opposites always go together, each one actually contains a bit of the other.

On the fundamental level therefore, neither can actually win. It’s just a dual that goes on and on, never crowning a victor.

In your obstacle contains the way. And in your way contain obstacles. It can’t be any other way.

Remember that next time you need help with acceptance. It’s just a game, and the point is to play.

Let me use an example from my own life.

Back in October, I shared the story with you guys about the spiritual awakening experience. I talked about how at the time, it was actually extremely painful and even sunk me into a depression.

That’s an obstacle. But I chose to look at that situation and say “I can use this”. That story has inspired many people and has been the source for the majority of content of

No spiritual awakening, no blog.

And maybe even meaningful, I’ve been able to use it to steer others from having the same experience unnecessarily.

The obstacle became the way.

So that’s nice and it makes me feel good. I want to place the emphasis that this was a CHOICE. I could have decided not to do any of that, create a victim mentality around it and just assume the world was against me. But that’s not the story I wanted to write.

We’re all just writing a story here.

What do you want yours to say?


Perception alone won’t change the external situation. You obviously have to take action.

But now that you’ve relinquished control, you can respond creatively and intelligently to the problem. You can apply persistence and will.

It only seems like a paradox on the surface that you could accept your situation and take action to change it. But if you apply this concept in real life you’ll see there’s no contradiction.


Where do we get strength of will from? Holiday talks about in this section how to develop that indomitable will that some people seem to have. And it runs very counterintuitive to our popular notions.

When people think of will, they usually imagine having a strong desire to get something for oneself. But that’s not what Holiday is talking about here.

The personal will is actually weaker than a collective will. If you look at the great historical movements like Civil Rights back in the mid 1900’s, you’ll see that people are willing to go far beyond just what is good for “themselves”. People will sacrifice themselves for a cause or ideal that affects others.

This is a paradox. In other reviews like Pursuing Consciousness I’ve talked about how people fundamentally follow their self-agenda. So what gives?

The self-agenda is a complicated thing. When people talk about sacrificing themselves for an ideal, that can be because of the self-?agenda. However for practical purposes we will say this kind of person is being selfless.

We touched on in Man’s Search for Meaning that it’s actually the transcending of Self where man thrives. Holiday’s theory is no different.

When you become less of the “poor little me”, you actually become more.

The corollary to this is the practice of death awareness. By meditating and really coming to grips with the fact that you will die, a person actually becomes more. They have more motivation, less fear, less ego, more love.

So that’s the main juice from the book. I really encourage you to take this on as a philosophy of life. Ryan Holiday has the words The Obstacle is the Way tattooed on his arm as a reminder for a reason.

One final radical conclusion from all this: failure does not exist.

I don’t mean like in theory. I mean actually. If a failure or obstacle only launches you to the next level, then was it even a failure?

Contemplate that for homework.

Who Will Love It



-Single moms / dads

-Struggling students


-History / philosophy nerds

-Anyone who wants more happiness out of life

-Anyone who is facing an obstacle

Who Will Hate It

-People who are identified with being a victim


-People who are afraid to give up control

-People with low self-trust

-People who can’t think in shades of gray

Why Does It Suck

There’s nothing inherently bad about this book and it’s nice to get Holiday’s perspective. But if you’ve read a lot of stoic or eastern philosophy, these ideas probably won’t be very new to you. He’s pulling a lot from other thinkers / authors. A minor point to consider.

The Wrap Up

Great book. If you feel like you’ve got an insurmountable challenge in your life, dig into this. The advice is practical as well as timeless. And it will give you a completely different perspective on how to handle the obstacles we all must face, no matter our Vision.

Buy The Obstacle is the Way here on Amazon!: