What Stands in Your Way Becomes THE Way

The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph by Ryan Holiday

The way we perceive difficulties and failures can predict how things are going to work for us at least for the next few years. It’s up to us to design our own future by developing a healthy mindset and embracing obstacles as interim steps in our way to success. Because Ryan Holiday‘s book gives us a great incentive to re-think things.

Look what I discovered. Check below the impressions I’ve shared in the books summary and the nuggets (visual quotes from books) I’ve selected from this book.

What do Marcus Aurelius, Mahatma Gandhi and Steve Jobs have in common? What do I have in common with any of them?

The more I was reading this book, the more I was curious which will be the answers to these questions.


“On the path to successful action, we will fail—possibly many times”.

As I found out reading Ryan Holiday’s “The Obstacle is The Way”, we all deal with obstacles. We all have something within us that we can use in overcoming them.

Starting from Marcus Aurelius famous quote – “What stands in the way becomes the way”, Holiday shows us how to transform our lives. The key? By changing the way we see life and its obstacles. And he does that in a very courageous way, presenting us the best practices of Stoicism and philosophy. Don’t worry! Holiday’s style of addressing doesn’t resemble any annoying academic lecture you might thinking of. In fact, he restores philosophy as “an operating system for the difficulties and hardships of life”.

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I have to admit that Holiday’s book helped me a lot to understand how obstacles should be managed. Not by preaching magic tricks, but by offering clear and simple thoughts of practical wisdom. This book is a useful guideline for understanding, appreciating, and acting upon the obstacles that unexpectedly come from daily life.

Furthermore, he does that with an empathic understanding of our common perspective on life. And this makes you grow fond of him page by page.

“What holds you back?”. Holiday offers us plenty of examples about people who overcame great obstacles by having the right perception, acting with nerve, perseverance and persistence.

Pericles, Demosthenes, Abraham Lincoln, George Washington, John Rockefeller, Amelia Earhart, Mahatma Gandhi and Steve Jobs. Those names sound familiar for you?

The Obstacle is the Way

Almost every chapter begins with an inspiring lesson of life from people like thee, presenting us the steps we must take for building a great life. So, let’s take these steps one by one.

In this book you’ll find three key concepts: perception, action & will. The first step is perception. “Perception is everything”, as Ryan Holiday states. This is the first thing we must considerate to change in order to overcome obstacles.

'Our perceptions can be a source of strength or of great weakness.' @RyanHoliday Click To Tweet

The good news is that “our perceptions are the thing that we’re in complete control of”. Having the right perception means seeing things simply and straightforwardly, as they truly are—neither good nor bad.

If we do so, we’ll come to see that obstacles are actually opportunities to test ourselves, to try new things, and, ultimately, to triumph.

By turning wrong perceptions into right perspectives, we discover their sources and how they can be solved. This is when we must prepare for action.

'Right action follows the right perspective.' @RyanHoliday Click To Tweet

Just as perception, action is a discipline, and Ryan Holiday dedicates a wide space from the second chapter to this topic. As a discipline, it’s not any kind of action that will do, but directed action. We must meet our problems with the right and effective action, and we must act with deliberation, boldness, and persistence.

This doesn’t mean that, acting in this way, we’ll easily overcome every obstacle we encounter. We should admit failures as a natural part of our way to success.

In Holiday’s words “on the path to successful action, we will fail—possibly many times”.

It’s just a matter of luck, after all “action and failure are two sides of the same coin”. But he also gives us the tools we need most when this happens.

The Obstacle is the Way

Besides perception and action, the discipline of overcoming obstacles requires a last critical step – Will.

“If Perception and Action were the disciplines of the mind and the body, then Will is the discipline of the heart and the soul.”

We must understand WILL as fortitude and wisdom. Will is our internal strength. WILL is the “strength to endure, contextualize, and derive meaning from the obstacles we cannot simply overcome”.

The will is what prepares us for a world that is inherently unpredictable and allows us to thrive and be happy in spite of it. How can we do this? Holiday makes a list of the choices we can make in every situation, based on our will:

  • prepare ourselves for more difficult times
  • accept what we’re unable to change
  • manage our expectations
  • persevere
  • learn to love our fate and what happens to us
  • protect our inner self, retreat into ourselves
  • submit to a greater, larger cause
  • remind ourselves of our own mortality
  • prepare to start the cycle once more

Put in the right context, every thought of wisdom from the list above becomes a step. And every step can be easily accepted as necessary, once we understand its importance.

After reading “The Obstacle is the Way”, you will no longer wonder how the obstacle becomes the way. You will be connected with the right perspective. Prepared for the right action. And discovered the will. All these together will make you not only a person of action, but a modern philosopher.

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