Book Summaries Philosophy

The Obstacle is the Way Summary

The Obstacle is the Way Summary

The ancient Greeks had many philosophical schools, but the most pragmatic among them was stoicism, and this may explain why in the practical, modern world, it has gained in popularity.

Ryan Holiday was a student of Robert Greene, there are many parallels in his style, when it comes to the structure of the book, and there is, of course, a more obvious parallel, in that both authors embrace the importance of seeing the world as it is, and not how it should be.

We normally see obstacles as inconveniences or hindrances to our ultimate goals. But building on the teachings of the ancient stoics, Holiday insists that this just an example of bad perception. Instead, you should see every obstacle as an opportunity, to improve, to focus, and to work harder and more effectively.

How you perceive the world will define your behavior, and if you choose to perceive it in the wrong way, you will dig yourself into a hole that may be too hard to get out of. So, you better get your perception right, as early as you can.

Without us, a subjective agent, there is nothing good or bad. There is only the event and the story we tell ourselves.

There are three stages involved in confronting obstacles: Perception, Action, Will. 

Holiday divides the book into three main parts, with each part dealing with one of the strategies. Below are summaries of each.

The Discipline of Perception

Musashi, swordsman and author of The Book of Five Rings notes the difference between observing and perceiving.

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The Discipline of Action

Demosthenes was born sickly and frail with a severe speech impediment. He lost his father at age 7. The large inheritance left to him was stolen by the guardians entrusted to protect him. 

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The Discipline of the Will

Abraham Lincoln battled with depression his whole life. It was known as melancholy at the time, it nearly drove him to suicide.

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A Zen Story

There is an old Zen story about a king whose people had become soft. The king was unhappy with this, so he decided to teach them a lesson. He placed a large boulder in the middle of the main road, blocking entry into the city. He then observed how the people would react from a distance. With disappointment, he watched as each person approached the boulder, and at best, tried halfheartedly, before giving up. Several days later, a lone peasant was on his way to this city. Unlike the others, he didn’t give up. He kept trying to push it until finally, an idea came to him. He went to the woods to find something he could use for leverage. He found a large branch and used it to create a lever to move the rock.


Sometimes, to get what you want, you need to be conniving. You need to use a strategy that is not too obvious. When nothing is working, it is important to adapt, and to try many different strategies. 

A big mistake is to be so focused on the result, that you plunge into work, but you don’t pause to examine whether your strategy is working, or whether you even have the right goals. 

There is nothing shameful about cutting your losses and moving on to something else, or admit that a strategy failed and to think of a new one. 

When times are good, you should be the most vigilant. It is during good times that people become soft and complacent. But don’t allow that to happen to you. If you are wealthy now or you have time for leisure, don’t assume that things will stay this way. Always expect the worst. 

The mental advantage this gives you is that when the worst does come, you will not panic like most people, you will more quickly focus your energy on something useful. 

Abundance as an Obstacle

Everyone knows that obstacles are real, but if you think about what great people have taught us, it is that we can turn any disadvantage to an advantage. Athletes who were too small, dreamers ahead of their time, dreamers and dyslexics, immigrants, and nouveaux riches. Anyone who came from nothing, from a place when their existence was threatened every day.

A lot of our problems in the modern world come from having too much. Technological disruption is too fast, junk food is too plenty, and traditions that lie to us about how we should live. We are soft, entitled, and afraid of conflict. Great times make people soft.

"A gilded No is more satisfactory than a dry yes" - Gracian

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