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The Obstacle is the Way by Ryan Holiday - 3 Big Ideas

Transcription Below


This book made me feel stoic, resilient and in control.

Quick Intro

This book is 224 pages long hardcover and six hours seven minutes long audio

It is advertised on Amazon as follows:

"The Obstacle is the Way has become a cult classic, beloved by men and women around the world who apply its wisdom to become more successful at whatever they do.


The book draws its inspiration from stoicism, the ancient Greek philosophy of enduring pain or adversity with perseverance and resilience. Stoics focus on the things they can control, let go of everything else, and turn every new obstacle into an opportunity to get better, stronger, tougher. As Marcus Aurelius put it nearly 2000 years ago: “The impediment to action advances action. What stands in the way becomes the way.”

Ryan Holiday shows us how some of the most successful people in history—from John D. Rockefeller to Amelia Earhart to Ulysses S. Grant to Steve Jobs—have applied stoicism to overcome difficult or even impossible situations. Their embrace of these principles ultimately mattered more than their natural intelligence, talents, or luck.

If you’re feeling frustrated, demoralized, or stuck in a rut, this book can help you turn your problems into your biggest advantages. And along the way it will inspire you with dozens of true stories of the greats from every age and era."

So, what are three things you can use from this book?

3 Things You Can Use

1. Good Vs. Bad is a Perception

Situations are neither good nor bad. Our perception defines the situation.

This is not about what Ryan Holiday calls, "wearing rose colored glasses," this is about a real inner understanding of the world around us.

Going back to the idea of a paradigm, if you consider what goes on around you as situations where each response is another Lego block that attaches on to and affects your personality, then you will consider your responses much more seriously.

What he, and the stoic philosophy, is getting at here is that each adverse situation can either make you stronger, by having you grow emotionally, mentally, physically or as a combination, or make you weaker by having you water the seed of reaction that puts your circumstances in charge of you rather than putting yourself in charge of you.

Don't let circumstance be your master. Use perception to recognize the good in each situation, that is obvious in positive circumstances and is practice and growth and resilience in negative circumstances. Use this philosophy and realize that, as the book says, "problems are never as bad as we think- they are precisely as bad as we think."

...for there is nothing either good or bad, but thinking makes it so...


2. Persistence Never Loses

Pursue your goal continuously with iteration.

From the book: "Action and failure are 2 sides of the same coin. One doesn't come without the other. What breaks it down is when people stop acting after taking failure the wrong way."

See, I just launched my website about a month ago. I was listening to all of these successful people on podcasts and seeing their results and so I had set myself a goal of getting 100 website subscribers by the end of that launch day.

So I planned it all out and I'm all excited and then I launch. By the end of the day I've added seven subscribers, not 100- and 2 of those subscribers was the same person using 2 different email addresses.


There is a way to have gotten 100 subscribers- my particular way got seven. This book tells me that I can either take it personally or use it objectively and create a plan of action and persist.

So hopefully, one day, Average Optimized will be much more popular and everyone on the earth will be subscribed to it- and I will be able to look back and think, "I'm glad I didn't take those few few subscribers personally and decide to quit. I'm glad that I decided to persist."

Feedback and iterations are important obviously and doing the same thing over and over again expecting different results is literally the definition of insanity, so there are some common sense caveats to this but one thing is for certain- persistence never loses.

3. The Inner Citadel

From the book: "That fortress inside of us that no external adversity can ever break down. (...) We are not born with such a structure, it must be built and actively re-enforced.

In the good times, strengthen so in the bad times you can rely on your strength. (...) Every adversity is another opportunity to strengthen your inner citadel."

This goes back to the first part about how your perception regarding good and bad, changes how you respond. Your response is that Lego that attaches to your personality. And that Lego structure is your inner citadel.

What he is saying here has to do with the old saying, "Your mind is a garden, your thoughts are the seeds. You can grow flowers or you can grow weeds." The more you practice your virtues in times of adversity, the more you build upon and strengthen that virtue, making it easier and easier for that virtue to be your go-to.

We can all strive to build our biggest inner citadel by living a life of healthy perception, choice and virtue.

A Few Words:

This was a good book. This book was influenced by the great stoics, Seneca the Younger, Epictetus and Marcus Aurelius.

This book is full of great stoic wisdom that Ryan Holiday describes anecdotally and then in-depth.

The audio version ends with a cool interview with Ryan Holiday and Tim Ferriss, set to the same freeflow interview style of Tim Ferriss' podcast.

I recommend this book to anyone. We all occasionally struggle with reacting rather than responding and we sometimes find ourselves influenced by our environment more than we would like to be.

Want to Read it?

Audible Free Trial (get this book for free!)

The Obstacle is the Way (Audible Version)

The Obstacle is the Way (Physical Copy)

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Punching Sounds (in video) by: Mike Koenig

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