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The Obstacle is The Way: Book Summary


I am someone who loves reading and constantly learning. So I thought it would be a great idea to share with you guys the books that have had the greatest impact on me in hope that maybe they can do the same for you.  

And what better book to start off my first book summary than Ryan Holiday’s incredible book “The Obstacle is the Way”.


I can honestly say that this book forever changed my perspective on life and I am a better person from having read it.

I would put it down as one of the greatest books I have read. I mean that.

And hopefully, this short summary of the 7 biggest lessons I took away from the book can inspire some of you to go out there and pick up a copy of this incredible book.


Summary in a Sentence:

The Obstacle is the Way teaches us that the seemingly negative situations of our life can not only be overcome but used as a source of strength and growth. It draws on lessons from ancient heroes, former presidents, modern actors and athletes who turned adversity into success. Using the power of perception, choice, action and will.


About the Author:

Ryan Holiday is the author of 6 books and an extremely successful blog, Ryan covers a lot of topics largely surrounding personal and business development. He has a passion for philosophy & stoicism as well as marketing, business, success, growth, marketing, self-awareness, and learning. He is the founder of the daily stoic.

Favourite Quote from the Book:

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





Lesson 1: Perception

the obstacle is the way summary


One of the central themes of the book and the first step to transforming obstacles is perception. The book defines perception as:


“How we see and understand what occurs around us and what we decide these events mean.”


You see each of us chooses the way that we perceive the world.


So it is important that we ask ourselves whether our perception is truly giving us perspective or whether our perception is actually what is causing the problem.


You see we each come across obstacles, that’s just life. But what matters most is not necessarily what these obstacles are but how we choose to see them and respond to them.


Where one person sees crisis another sees opportunity. Holiday says that with the right perspective we can choose to see the opportunity that is inherent within every obstacle.

And transform that negative situation into a skill set, an education, a fortune or a way to help others. With the right perspective says holiday;


“Everything that happens to us can be seen as a way to move us forward.”


Lesson 2: The Power of Choice

the obstacle is the way summary

Ok, so the second important lesson from the book is the power of choice that each of us has in our lives.


A quote which from the book that sums up this precept well is one by Marcus Aurelius who said:


“Choose not to be harmed and you won’t feel harmed. Don’t feel harmed and you haven’t been.


You see we each have the innate power within us choose how we will respond to any situation.


One of the most powerful stories in the book and one that left a lasting impression on me was the true story of Rubin Carter AKA “The Hurricane” who was wrongly accused because of his ethnicity a crime he did not commit.


Triple homicide.


And was sentenced to three life sentences in prison.


Now most people if something like this happened to them would likely give up.  


But not Carter.


Instead of breaking down Carter declined to surrender the freedoms that were still his: his attitude, his beliefs and his choices.


No matter what he was faced with in prison, Carter maintained that he still had choices. Choices that could never be taken away from him. So he refused to sink into despair.


He told himself “I may not have wanted this to happen to me, but I decide how it will affect me. No one else has that right”


So he chose to use every second of his energy reading books on law, philosophy, history. He maintained the belief that no matter what he would leave the prison not only a free man but a better person because of it.



And it paid off because after 19 years and two trials Carter was able to successfully overturn his trial and left prison a free man.






Lesson 3: Control Your Emotions


the obstacle is the way summary

Ok, so the next lesson of the book is to control your emotions. You see a lot of the time when negative situations come up in our lives what most of us tend to do is allow ourselves get lost into worry.


Which of course is only natural, but not really all that helpful to our situation. Instead what Holiday suggests that when we worry we should use Gavin Debeckers advice and ask ourselves these two questions


“What I am choosing not to see right now?




“What important things are missing because I am choosing worry over introspection, alertness or wisdom?”


Or as Holiday puts it


“Does getting upset really provide you with more options?”


Most likely the answer is no. So instead of wasting your time worrying…

Lesson 4: Take Action


the obstacle is the way summary


So the next big lesson of the book is too take action. You see what is the main thing that most of us do when problems come up in our lives? We ignore them. We pretend they don’t exist.


But we deep down that this isn’t going to make our problems any better. Instead what we need to do. Is act. To get started and get moving in whatever way possible. Because the problems in our lives aren’t just going to solve themselves, it is up to each of us take the responsibility into our own hands.


Lesson 5: Break it Down


the obstacle is the way summary


The next big lesson from this book and the one that precedes action is breaking our situation or problem down into smaller parts.


Now at the time in my life when I was reading this book and I felt like I had a lot of things against me. And this idea changed everything for me and is something I now carry with me whenever I have things come up in my life.


Basically what you do is focus on breaking the problem down into smaller more manageable parts.


By focusing on one task at a time.


Completing it.


And then moving onto the next.


One day at a time.


Under this process, we no longer need to allow ourselves to sink into worry or overwhelm, because now what once seemed like a mammoth or even impossible task is now just a series of component parts.


One of the most profound analogies of the book is Holidays comparison of the problems in our lives to that of algebra equations we were given at school.




Well at first, they were just a bunch of simples and unknowns and probably looked impossible to solve. But once you stopped, took a breath and broke them down. You were able to isolate the variables, solve them and all that was left was the answer. The same thing can be done with the problems in our lives.


Lesson 6: Find the Good


the obstacle is the way summary


Ok, so the next big lesson from the book is to find the good in your situation. Because no matter how bad a situation may be.

There is always some good in it.  Holiday believes that cheerfulness is important in all situations of life be they good or bad.

I highlighted this quote from the book which I think sums up this idea perfectly;

“We don’t get to choose what happens to us, but we can always choose how we feel about it. And why on earth would you choose to feel anything but good?”


Lesson 7: Find Your Why


the obstacle is the way summary


Ok, so the final biggest lesson from the book and probably the one that had the most impact on me and has helped me during trying times in my life is finding your why.  


There is a quote from the book that sums up this idea perfectly. It is actually a quote from the incredible book,”Man’s search for meaning”, another book I would highly recommend.


The quote is:

“He who knows the why of his existence can bear almost any how”. – Victor Frankl


Holiday teaches that the best way to see yourself through the obstacles in your life is to dedicate to something larger than yourself.


That is to say, that when you know what it is you’re setting out to do, everything that happens to us from that point onwards becomes in service of that dream. Put simply it becomes purposeful.


Holiday also speaks of how we can use the seemingly negative situation or circumstances we have found ourselves in and use as a way to improve ourselves.


By taking everything that we learn from it and turning it into a skill set, an idea, an education or a way to help others.

He also says that we should take our focus off of ourselves and instead think of other people out there who need us now or may need us in the future. Because by being strong for others it makes us stronger.



Favourite Quotes From The Book:


“When you have a goal obstacles are actually teaching you how to get where you want to go – carving you a path”


“Obstacles are actually opportunities to test ourselves, to try new things, and, ultimately to triumph.”


“Where one person sees crisis, another person sees opportunity.”


“We can learn to see opportunity in every disaster, and transform that negative situation into an education, a skill set, or a fortune. Seen properly, everything that happens to us can be used as a way to move us forward.”


“Remember that this moment is not your life, it is just a moment in your life.”


“Life is a process of breaking through these impediments… Each time, you’ll learn something. Each time, you’ll develop strength, wisdom and perspective. Each time a little more of competition falls away. Until all that is left is you: the best version of you.

Well, there you have it guys. These are my 7 biggest takeaways from the book. But this is only a small part of this truly incredible book, it is honestly one of the most powerful books I have ever read. And continues to stay with me today.


I honestly believe it is a book that every person should read. Especially if you feel like you are going through a rough patch. This book will not only see you through it, but it will change your perspective and allow you to find the inherent lesson or growth within your so-called “obstacle”.


I would highly recommend that you go out and get yourself a copy of this book. You won’t regret it.


Want to see this as a visual summary? Check out my summary video.


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