The Obstacle is the Way: Book Summary

by | Jul 27, 2021 | Reading

One trait that separates the “successful” (however you define it) from those who lack consistency with their results, is the way they view obstacles. Those who accomplish a lot see obstacles not as setbacks but as opportunities.

I just recently read Ryan Holiday’s book The Obstacle is the Way and I really enjoyed it. Holiday is a self-proclaimed Stoic and he takes this ancient philosophy and applies it to modern times.

In this book, Holiday gives a blueprint on how we can respond better to adversity through reshaping our perception, acting on the opportunity presented to us, and persevering regardless of the results.

I don’t agree with every premise in this book, but I do think Holiday does a really good job of sharing time-tested philosophy and showing the practical application.

If you are interested in this topic, I think you’ll enjoy this summary of the book through some of my highlights. 



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



    • What is Perception? It’s how we see and understand what occurs around us — and what we decide those events will mean.
    • 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.”
    • Focusing exclusively on what is in our power magnifies and enhances our power.
    • Where the head goes, the body follows. Perception precedes action. Right action follows the right perspective.



    • Action is commonplace, right action is not. As a discipline, it’s not any kind of action that will do, but directed action.
    • In a world where we increasingly work for ourselves, are responsible for ourselves, it makes sense to view ourselves like a start-up — a start-up of one. And that means changing the relationship with failure. It means iterating, failing, and improving.
    • To be physically and mentally loose takes no talent. That’s just recklessness…to be physically and mentally tight? That’s called anxiety…physical looseness combined with mental restraint? That is powerful.
    • As Duke Ellington once said, “Problems are a chance for us to do our best.”



    • What is Will? Will is our internal power, which can never be affected by the outside world.
    • This is the avenue for the final discipline: the 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. The Will is the one thing we control completely, always.
    • It doesn’t always feel that way but constraints in life are a good thing. Especially if we can accept them and let them direct us. They push us to places and to develop skills that we’d otherwise never have pursued. 
    • To do great things, we need to be able to endure tragedy and setbacks. We’ve got to love what we do and all that it entails, good and bad. We have to learn to find joy in every single thing that happens.


Final Thoughts: The Obstacles Become the Way

    • See things for what they are. Do what we can. Endure and bear what we must. What blocked the path now is a path. What once impeded action advances action. The Obstacle is the Way.


Game Plan

First, I highly recommend reading this book. Second, what is one obstacle that is currently standing in the way of you accomplishing a goal? Ask yourself these questions:

    1. Am I seeing this situation in the right perspective or am I creating a story? Maybe you need to reframe your perception.
    2. What’s the next step I can take? See the opportunity in this obstacle.
    3. What can I learn about myself through this situation? Use this as a learning moment.


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