The Obstacle Is the Way by Ryan Holiday [Summary]

This is a comprehensive summary of the book The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph by Ryan Holiday. Covering the key ideas and proposing practical ways for achieving what’s mentioned in the text. Written by book fanatic and online librarian Ivaylo Durmonski. Supporting Members get full access.


“Let’s talk about failure and how to deal with obstacles,” is kind of what Ryan Holiday said when starting to write this book. While tiny, The Obstacle Is the Way covers a lot of ground. By sharing various stories of history’s most famous names, Ryan Holiday wants to inspire us. To give us the mental tools we need to deal with hardship and spot opportunities in even the cruelest situations life throws at us.

The Core Idea:

Mr. Holiday argues that to get better at overcoming obstacles you need to be skilled at three disciplines: perception, action, and the will. This trio of steps, and the accompanying substeps, are going to ease your way uphill. Yes, it’s always uphill. There are always more obstacles to come. The more you accomplish, the more things will stand in your way.


  • The better version of yourself is waiting on the other side of the hurdle.
  • Don’t believe the person saying you can’t do it. Use his negativity for inspiration.
  • It’s not going to be easy. Actually, it’s supposed to be hard.

The 5 Key Lessons From The Obstacle Is the Way:

Lesson #1: The Obstacle Becomes The Way

There’s a big rock standing in your way? You should definitely move it. That’s now your main task in life.

That’s pretty much the main topic of the book. Whatever stands in your way, becomes the way.

And these are not my words, neither the words of Ryan Holiday. In fact, a very powerful man said it first: Marcus Aurelius. Here’s what he stated:

The impediment to action advances action. What stands in the way becomes the way.” Marcus Aurelius

Regardless of your financial situation, your background, and your rank in the company you work for, there are always obstacles. Always difficulties trying to sabotage your existence: workers protesting against you, rising unemployment, network failure crashing your whole system, a nasty disease that strikes your siblings, a high school bully who’s making your life difficult, etc.

Identify the obstacle that is blocking your path and don’t turn away. Analyze the situation. Look for opportunities. Search for solutions. Then, act. Push till you’re over the hurdle. On the other side, a new person is going to greet you. Your new improved self.

The obstacle in the path becomes the path. Never forget, within every obstacle is an opportunity to improve our condition.” Zen Proverb

Lesson #2: Spot The Opportunity in Every Disaster

Obstacles feel paralyzing. That’s normal. Even common these days. After all, in the cozy 21 century with fresh water, electricity, the holy internet, we expect everything to be effortless, easy, pain-free. But it’s not. And when it’s not, when things are not working out the way we want them to, we start to panic.

When we’re facing a difficult situation, we feel distressed and we call our parents for help. Or worse, hide behind our desk, in the basement, or eat the whole jar of chocolate.

It’s of major importance to understand that our lives are not, and never will be, hurdle-free.

On a daily basis, we’re facing difficulties that either help us improve or make our lives miserable.

Regardless of what stands in your way, the way you see the problem is what matters. If you consider a task impossible, this will mean that it’s impossible.

Or in other words, we have the choice to decide whether something can be done or cannot be done. Our perception plays a major role in our problem-solving rodeo.

If you’re accused, thrown out of your comfort zone, facing seemingly impossible to handle challenges, don’t let your emotions control you. Steady your nerves. Ignore the one who says that what you’re trying to do is impossible. Place things in perspective and find the best course of action to move forward.

Hey there, sorry to interrupt…

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