Obstacle Is the Way Summary – The Best Advice From Stoic Philosophy

The Obstacle is the Way an international bestseller, written by Ryan Holiday, In the book, Holiday outlines how to use ancient Stoic philosophy as a way to overcome any obstacle in life.

Obstacle Is The Way Summary

In the book, The Obstacle is the Way, Holiday outlines how to use ancient Stoic philosophy as a way to overcome any obstacle in life.

In The Obstacle is the way, the author takes an intriguing look at how some of the most successful people in history sought obstacles before going around them.

It is also is full of well-told stories and anecdotes that illustrate Stoic lessons about overcoming obstacles.

Reading these stories and adopting this mindset can be a proverbial game changer for any reader looking to build strength for the long-term.

Best ideas from the Obstacle is the Way

As I mentioned there are three main ideas and concepts that is key in this book:

  • the importance of perception
  • the importance of action
  • the importance will


One of the first concepts presented in The Obstacle is the Way, perception.

Holiday argued that we have to look at what others might see as obstacles and make them work for us because they are not innately bad or good.

We can turn any obstacle into an opportunity by changing our perspective about it. This means thinking through how a certain circumstance might benefit us or prepare us for future challenges instead of dwelling on its potential negatives until it becomes insurmountable.


Action is also key when facing challenges in life according to Holiday’s philosophy – taking action will always beat sitting around waiting for things to happen which usually never does anyway! We need to take action with every being aware that there will be moments where even if we take action, things will not happen the way we want them to.

A great story he shares about the importance of taking action is the tale of how he had a friend who was working on starting his own company.

The friend would often want to get feedback and opinions from Holiday, but when it came time for him to ask questions, he never wanted to take action in response – if people said that they liked an idea or didn’t like one then he still wouldn’t do anything with it. He continued this pattern until eventually nothing moved forward at all because there were no ideas being acted upon.


The last important idea he shares in the book is the importance of will. It’s about the stuff that gets you back up when you’re knocked down and is what will get us through all of life’s obstacles.

My favorite story he shares about the importance of willpower is the story about Abraham Lincoln. In 1858, Lincoln was at the bottom of his career. He had suffered several major losses and faced a series of economic setbacks that left him in deep debt. But he didn’t let any obstacles stop him from running for president two years later.

Who should read The Obstacle is the Way?

We think that you should read this book if any of the following apply to you:

  • You are looking for an inspirational and motivating read that will teach you how to overcome obstacles in life.
  • If you want a book on practical philosophy, rather than academic theory, this one is perfect.
  • You are interested in creativity; seeking out new perspectives; discovering ways we can create our lives
  • It may be helpful if your goal is to discover new ways of thinking

Who should not read this book?

You should not read this book:

  • If you are looking for a book that will provide step-by-step practical advice on how to get out of your own way.
  • The Obstacle is the Way may not be helpful if one of your goals in life is to create less obstacles, rather than more.

What you can learn from The Obstacle is the Way

If you read this book, you can learn how to:

  • See what you’re really made of
  • Strive for difficult goals with more tenacity and vigor than before.
  • Manage your fear, doubt or worry

You will also learn how to:

  • Recognize that while obstacles may be difficult, they’re not impossible. You can take heart in knowing that
  • Find the strength inside you to keep going, even when the odds are stacked against you.

Best Quotes from Obstacle is the way

  • “Think progress, not perfection.”
  • “Focus on the moment, not the monsters that may or may not be up ahead.”
  • “Wherever we are, whatever we’re doing and wherever we are going, we owe it to ourselves, to our art, to the world to do it well.”
  • “Where the head goes, the body follows. Perception precedes action. Right action follows the right perspective.”

Review of the Obstacle Is The Way

Most of the reviewers online are in agreement that the book is:

  • Practical.
  • Relevant to anyone who has a goal, no matter how big or small.
  • Interconnected with other ideas about success and failure which means it can be used as inspiration for many different fields of work.

The Obstacle is the Way also includes some great advice on how to handle the obstacles and so far I have found it very helpful.

Reviewers who did not like the book that much said that it was:

  • Too repetitive.
  • bit too over the top in some areas and not always clear on what he is trying to say.

I would say that the advice in this book is not new, but that’s because it works! You get some great insights into how to overcome your fears or worries as well as a fresh perspective on what success really means


Hope you found this summary of the Obstacle is the Way insightful and useful.

I would recommend reading this book if you are someone who: wants some practical advice on dealing with tough times and/or loves ancient philosophy because it has a good mix between modern day examples combined with quotes by philosophers like Seneca, Marcus Aurelius and Epictetus.

Marilyn Nissen
Written by Marilyn Nissen

Marilyn Nissen is the founder of BestSellerSummary.com, a highly reputable book summary and reviews website. With over a decade of experience in summarizing and reviewing books, Marilyn is a trusted authority in the book industry.