The Obstacle Is the Way Summary

Life is always throwing some obstacles and hardships at you in your quest to truly become who you were destined to be. But how do you conquer? “The impediment to action advances action. 

What stands in the way becomes the way.” This is what was said by Aurelius over 2000 ago and is the inspiration for the book The Obstacle is The Way by Ryan Holiday. In his book, Holiday looks at the formula to success that has been used by many icons in history. 

This Obstacles is The Way summary discusses the profound teachings impacted upon the reader by Holiday. Read on to get a glimpse of the amazing formula that many pundits in different arenas of life believe in.


Perception is how you see and understand what occurs around you, and what you let those events mean to you. To overcome your obstacles, you must have the discipline of perception. This means you should be able to separate reliable signals from deceptive ones. This allows you to see things as they are. 

The greatest investors of all time, Rockefeller and Warren Buffet have exercised the discipline of perception which is what has got them this far. As Warren Buffet puts it “be fearful when others are greedy and greedy when others are fearful.” Learn from the difficult moments so you can be able to turn them into a way. Choose not to give in to the feelings of desperation, despair, fear, and hopelessness. 

When you have mastered perception you will be able to see a crisis when others see an opportunity or when others are blinded by success, you can see the reality of the situation as it is. You become objective to available opportunities. You should separate your emotions completely from your investment decisions and learn to think differently than other people. The chapters under part one of the book are;

  • The discipline of perception
  • Recognize your power
  • Steady your nerves
  • Control your emotions
  • Practice objectivity
  • Alter your perspective
  • Is it up to you?
  • Live in the present moment
  • Think differently
  • Finding the opportunity
  • Prepare to act


In the first part, you learn how to completely identify the obstacles and isolate them by having the discipline of objectivity. Now, it is time to act. In this part of the book, Holiday states that not all kind of action will help you turn obstacles into a way. You must have directed action. This means that everything that you do is a part of the whole. It is purposeful. 

In the first chapter of the book, Holiday gives the inspiring story of Demosthenes. He was born with a speech impediment and was robbed of his inheritance by his guardians. To fight back, the boy had to teach himself speech and law. 

When he was of age, he surprised many because he had become a great orator. He soon became one of the greatest orators in Athens and even in the world. This is what action should be like. Everything Demosthenes did was directed to the final goal. He turned his obstacles of speech impediment and fear of bullies into his strength and success. 

To really overcome you have to stay moving always. You must be persistent and consistent in your action. Complacency can only mean others, and of course, your obstacles will destroy you.  In your course of action, you will experience failure. If this happens, you need to be prepared for it and keep changing course. Consider failure to be a feature. 

Be prepared for the worst case scenario always so you can have buffers and be able to use your obstacles against themselves. The chapters in part two are;

  • The discipline of action
  • Get moving
  • Practice persistence
  • Iterate
  • Follow the process
  • Do your job, do it right
  • What’s right is what works
  • In praise of the flank attack
  • Use obstacles against themselves
  • Channel your energy
  • Seize the offensive
  • Prepare for none of it to work


Finally, to turn your trials into triumphs, you must have a powerful will. Your will power should be flexible, resilient and humble. Theodore, Abraham Lincoln and other great icons in history have struggled with issues that could have broken them. Lincoln was struggling with depression which had led him almost to commit suicide twice. 

Theodore, on the other hand, was struggling with a severe case of asthma and a weak body. Without a powerful will, these great icons would not have become the people we know today. 

To have an unshakeable will, you must then learn to prepare for all negativity that may come your way, love everything that happens to you and meditate on your mortality. The chapters you will read under ‘Will’ are;

  • The discipline of the will
  • Build your inner citadel
  • Anticipation (Thinking negatively)
  • The art of Acquiescence
  • Love everything that happens: AMOR FATI
  • Perseverance
  • Something bigger than yourself
  • Meditate on your mortality
  • Prepare to start again

What I Like About the Book

I like that this book gives real examples of people that many can relate with. There are many historical icons from presidents, entrepreneurs, and people in all aspects of life have overcome many obstacles. It is highly relatable. The writing is concise and clear. I also like that the book can help people overcome barriers in many aspects of life.

Why You Should Read the Book

You should read this book if you keep hitting a wall in your endeavors and do not know how to overcome the obstacles. There are always obstacles in most of the things encountered daily. 

This book will help you to change your perception so you can clearly identify obstacles, be able to act in the right way to overcome and overturn the obstacles and have the will that will take you further so you can conquer even longer.

​Next summary: The One Thing

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