Book SummaryThe Obstacle Is The Way, by Ryan Holiday

1-Page Summary1-Page Book Summary of The Obstacle Is The Way

Life can sometimes feel like an endless string of problems and setbacks. But what if it didn’t have to be this way? What if, instead of exhausting you and dampening your spirits, every challenge you faced made you tougher and more energized? In The Obstacle Is the Way, Ryan Holiday argues that you have the power to create this kind of life for yourself by changing the way you view your problems.

Holiday explains that choosing to view obstacles in an empowering way is a major tenet of an ancient philosophy called Stoicism, founded in Greece in the third century B.C. According to Holiday, people throughout history have chosen to follow the Stoic tradition and utilized the same empowering strategy to solve their problems: They find the hidden opportunity in any misfortune and use it as a tool to accomplish their chosen goal. This philosophy has enabled people from every walk of life to overcome enormous obstacles and transform themselves into stronger, nobler people in the process.

This guide will teach you the tenets of Stoic problem-solving and how to apply them to the problems in your life. We’ll begin by explaining the basics of how Stoics view the world and the purpose of life—ideas that Holiday calls “The Discipline of Perception.” Then, we’ll explore specific strategies rooted in Stoicism that you can use to solve your problems: First, strategies to master your emotional state that Holiday refers to as “The Discipline of Will,” and second, strategies to efficiently accomplish your goals in the real world that Holiday refers to as “The Discipline of Action.”

Is This Really Stoicism?

It’s a point of contention whether or not The Obstacle Is the Way and other pop-Stoic texts truly fit into the Stoic canon. The Obstacle Is the Way doesn’t claim to be a replacement for the original Stoic texts or even to comprehensively summarize them—Holiday prefers to label it as a book “inspired by” Stoicism rather than one that’s “about” Stoicism. This qualifying statement begs the question: How faithful are the ideas in this book to the original Stoic teachings?

There’s no single founding document of Stoicism outlining exactly what the philosophy represents, but many ideas common across Stoic writings are present in The Obstacle Is the Way. Holiday agrees with the Stoics that through self-discipline, a “sage” can transform their life by becoming undisturbed by external events and learning to control irrational passions.

Holiday’s faithfulness to Stoic writing doesn’t stop there. The three disciplines that form the backbone of Holiday’s book—perception, action, and will—originated in the Roman Stoic text Discourses by Epictetus. These specific English names were coined by Gregory Hays in the introduction to his translation of Meditations by the Stoic emperor Marcus Aurelius.

However, The Obstacle Is the Way doesn’t perfectly represent the Stoic way of life. Holiday focuses his book on the ways you can use Stoicism to get what you want out of life by amending your approach to problems. Some argue this attitude undercuts the power of “true” Stoicism, which denies the need for material gain and puts greater emphasis on virtuous living. Holiday would likely make the case that while his book doesn’t paint a complete picture of the Stoic worldview, it doesn’t necessarily contradict it, either. As Holiday himself put it, “Stoicism is a philosophy designed for the masses, and if it has to be simplified a bit to reach the masses, so be it.”

Philosophy: Adopt an Empowering Worldview

We’ve distilled the Stoic problem-solving worldview into two basic truths. These truths are Holiday’s foundational beliefs about the world that lead him to conclude that you can (and should) transform any problem into an opportunity that benefits you.

Truth #1: No Event Is Necessarily Good or Bad

In our everyday lives, we assign meaning to everything that happens to us, judging events to be either good or bad. Holiday explains that in contrast, Stoics view events neutrally—that is, they observe only the facts of any given situation, without judgment.

In Holiday’s eyes, the positive or negative judgments we make about the events in our lives are nothing more than illusions—they’re often detached from reality. Additionally, Holiday argues that these subjective judgments themselves are what cause much of our suffering. Instead of seeing things as they are, we perceive problems that aren’t really there.

For example, imagine you hear a rumor that the company you work for is operating at a loss and several employees need to be fired. You fear you’re going to lose your job and begin to panic. Holiday would argue that the risk of getting fired isn’t the problem—your warped, negative view of the situation, causing fear and panic, is the problem. These feelings don’t necessarily reflect reality—even if you are fired, there’s a chance you might immediately find a better job, and getting fired will have been one of the best things to ever happen to you.

Cognitive Behavioral Therapy Is About Cultivating Objectivity

Holiday’s claim that subjective perceptions cause most of our suffering has significant support from the field of psychology. In the popular branch of psychotherapy known as cognitive behavioral therapy, or “CBT,” a patient and therapist...

The Obstacle Is The Way Summary Shortform Introduction

The Obstacle Is the Way is an instruction manual on how to solve life’s toughest problems, based on the teachings of the Stoics of Ancient Greece. Ryan Holiday argues that by adopting the Stoics’ historically proven formula for success, you can redirect the forces that typically work against you and will them to push you toward your goals. Once you embrace the truth that events are only “good” or “bad” if you perceive them that way, you gain the ability to transform your pain into power, your limitations into strengths, and your obstacles into opportunities.

About the Author

Ryan Holiday began his career after dropping out of college at age 19, when Robert Greene, author of The 48 Laws of Power, agreed to take him on as an “apprentice.” A year later, he got a job in the PR department of American Apparel, eventually becoming the company’s director of marketing. During this time, Holiday also founded his own consulting firm Brass Check, which has served such high-profile clients as [Tony...

The Obstacle Is The Way Summary Part 1: Philosophy | Adopt an Empowering Worldview

Life can sometimes feel like an endless string of problems and setbacks. But what if it didn’t have to be this way? What if, instead of exhausting you and dampening your spirits, every challenge you faced made you tougher and more energized? In The Obstacle Is the Way, Ryan Holiday argues that you have the power to create this kind of life for yourself by changing the way you view your problems.

Holiday explains that choosing to view obstacles in an empowering way is a major tenet of an ancient philosophy called Stoicism, founded in Greece in the third century B.C. The Obstacle Is the Way is a Stoic’s guide to solving problems, outlining the principles that heroes throughout history used to exert their will over a hostile world.

According to Holiday, people throughout history have chosen to follow the Stoic tradition and utilized the same empowering strategy to solve their problems: They find the hidden opportunity in any misfortune and use it as a tool to accomplish their chosen goal. This philosophy has enabled people from every walk of life to overcome enormous obstacles and transform themselves into stronger, nobler people in the process.

This guide will teach you...

Shortform Exercise: Look for Hidden Opportunities

In every situation or obstacle, there are hidden opportunities that you can turn to your own benefit. Finding them is a matter of viewing the obstacle neutrally (seeing it as it is, without judgment), then reorienting your thinking to see it as a gift rather than a problem.

Describe a problem or challenge that frustrated you this week. Why was it frustrating?

The Obstacle Is The Way Summary Part 2: The Internal Fight | Master Your Emotions

So far, we’ve established that Stoics view everything that happens as neither intrinsically good nor bad—instead, they believe that you determine whether something will positively or negatively impact your life depending on how you perceive the situation. Additionally, we’ve discussed how Holiday believes that your ultimate purpose should be to improve your life and the lives of others, and positively interpreting the events in your life will give you the strength to overcome obstacles on your way to this goal.

For the rest of this guide, we’ll be discussing specific strategies to help you accomplish this: ways to reorient your thinking and seize the opportunities within your obstacles. In this part, “The Internal Fight,” we’ll focus on Holiday’s internal, emotional strategies for success. These tips will help you avoid becoming demoralized by external events and keep you motivated to pursue your life purpose. (In the book, Holiday refers to this practice as “The Discipline of Will.”)

Introduction to Emotional Discipline

Stoic philosophers emphasize the importance of **emotional regulation—intentionally deciding which emotions you will allow to influence your...

Shortform Exercise: Practice Acceptance

When you’re facing a situation you can’t change, the only thing you can do is accept it. Once you do so, you can very likely find some benefit. Though you don’t get what you wanted, you gain something else worth celebrating.

Describe a negative situation in your life that you can’t change (for example, being required to share a small workspace with a coworker you dislike).

The Obstacle Is The Way Summary Part 3: The External Fight | Do What It Takes to Succeed

In Part 2, we began discussing specific strategies to help you accomplish your life goals and transform the obstacles impeding these goals into opportunities that move you forward. This first set of strategies had to do with internal, emotional discipline—intentionally shaping your own emotional state to push yourself toward virtuous action and withstand potentially demoralizing setbacks.

Now, in Part 3, we’ll conclude our discussion of strategies to help you achieve your life goals with a set of strategies to overcome obstacles in the external world. Holiday refers to these strategies as “The Discipline of Action,” difficult yet rewarding paths to success that require you to transform obstacles into gifts at every turn.

(Shortform note: Whereas Holiday frames the “Discipline of Action” as the ability to do whatever it takes to get what you want, the original Stoic Discipline of Action as laid out in Epictetus’s Discourses is synonymous with a life of virtue. This distinction stems from the Stoic belief that instead of chasing your desires and goals, _[virtuous action, based on...

Shortform Exercise: Be a Practical Pessimist

When making plans, consider what could go wrong in advance to prepare for or prevent problems. When you’ve anticipated a problem, you won’t be thrown off track or respond incorrectly if it comes to pass.

Describe a plan you’re making for an upcoming event—for example, for a trip, wedding, renovation project, or community event.

Shortform Exercise: Conquer Stubborn Obstacles

When you’re stuck on a problem, don’t be tempted to give up. Each effort is an opportunity to test ideas and learn; eventually, you’ll find the right one.

Think of a problem where you’ve tried multiple solutions, but nothing’s worked (for example, searching for a new job). What do you think makes this problem so difficult to solve?