The Obstacle Is the Way: Review & Critical Reception

This article is an excerpt from the Shortform book guide to "The Obstacle Is The Way" by Ryan Holiday. Shortform has the world's best summaries and analyses of books you should be reading.

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What is Ryan Holiday’s The Obstacle Is the Way about? What is the Stoic secret to staying calm and unperturbed in the face of adversity?

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.

The following The Obstacle Is the Way review covers the book’s context, background, and critical reception by the readers.

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 Robbins and Tim Ferriss. After releasing The Obstacle Is the Way, Holiday’s career as a nonfiction author took off, and he quit marketing to focus on writing full time.

Holiday first encountered Stoicism at 19. Holiday recounts that at this age, he made it a habit to ask as many successful people as possible for book recommendations. He read Marcus Aurelius’s Meditations after Dr. Drew Pinsky, host of the radio show Loveline, recommended it to him and credits this event as a pivotal moment in his life.

Holiday is also the founder of the Daily Stoic blog and currently hosts its daily podcast, offering bite-sized lessons in Stoicism and interviewing top performers from a variety of disciplines. He currently lives on a ranch in Texas, raising cows, goats, chickens, and other animals when he isn’t writing.

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The Book’s Publication

Publisher: Penguin Random House

Imprint: Portfolio

The Obstacle Is the Way is Holiday’s third book, published in 2014. The book originated from a guest post on Stoicism that Holiday wrote for Tim Ferriss’s blog in 2009. Impressed with the piece, a publisher approached Holiday with a deal for a book on Stoicism, but he declined the offer, as he didn’t think he was yet experienced enough to tackle such an important project. He shelved the book for several years.

Holiday became moderately infamous after the release of his first book Trust Me, I’m Lying (2012), an exposé of the Internet news media in which he confessed to manipulating online publications into spreading disinformation for free viral publicity. His reputation as a shady marketing expert faded with the release of The Obstacle Is the Way, replaced by a public image centered around Stoicism.

Holiday followed The Obstacle Is the Way with several other books on modern Stoicism, including Ego Is the Enemy (2016) and Stillness Is the Key (2019), which are sold with this book as a boxed trilogy. All three books are written in a similar style: short chapters of historical anecdotes intended to illustrate specific Stoic principles from a self-help perspective. Holiday also published The Daily Stoic with co-author Stephen Hanselman in 2016, a “daily devotional” split into a year’s worth of brief lessons in Stoicism. Holiday’s first book in a new series based on Stoicism’s cardinal virtues, Courage Is Calling, was published in 2021.

Intellectual Context

Holiday primarily draws his ideas from the Stoics’ original writings. He specifically cites the ancient works Meditations by Marcus Aurelius, Letters from a Stoic by Seneca, and Discourses by Epictetus as his main inspirations.

Holiday is far from the first person to bring these ideas into the modern age. Psychologist Aaron T. Beck, who in the 1960s developed what later would become modern cognitive therapy, credits Stoicism as the philosophical basis behind the therapeutic approach. In addition, academics turned greater attention to Stoicism as the topic of “virtue ethics” became popular throughout the late 20th century. Finally, the rise of the Internet and communities such as the Modern Stoicism Organization helped turn Stoicism into a major contemporary movement, as Stoicism’s self-help applications attracted a broad audience. Books like A Guide to the Good Life (2008) and Stoicism and the Art of Happiness (2018) capitalized on and contributed to this wave of pop-Stoicism.

Holiday argues that most modern books about Stoicism obscure its main ideas and end up reducing their core value. In Holiday’s eyes, the only other modern Stoic thinker worth reading is the French philosopher Pierre Hadot. He cites Hadot’s books Philosophy as a Way of Life (1995) and The Inner Citadel (2001) as successful attempts to clarify Stoic ideas for practical living.

The Book’s Impact

Soon after it was written, The Obstacle Is the Way became a cult classic among famous high performers, most notably professional athletes. Prior to their 2014 Super Bowl win, the coaches of the New England Patriots distributed copies of the book to the entire team. The media continued to report as players and coaches on other NFL teams, including the Seattle Seahawks and the New Orleans Saints, sang the book’s praises. The Obstacle Is the Way infiltrated the MLB (Chicago Cubs), the NBA (Miami Heat), and even the Olympics—athletes and coaches on the US women’s soccer and volleyball teams and US men’s wrestling and gymnastics teams swear by it.

The Obstacle Is the Way became more famous as celebrities from other fields professed their admiration, including Arnold Schwarzenegger, rapper LL Cool J, author Steven Pressfield, and NBC sportscaster Michele Tafoya.

This growing grassroots following eventually led to The Obstacle Is the Way becoming the #1 e-book on the New York Times bestseller list in 2019, five years after it was published. The New York Times credits Ryan Holiday for popularizing Stoicism as a self-help movement with this book.

Critical Reception

The Obstacle Is the Way received a positive review from Forbes on release, who described it as “an inspiring read for anyone faced with adversity,” but the book flew under the radar of other major publications.

Fans’ reviews of The Obstacle Is the Way were largely positive, celebrating the book as life-changing self-help and attesting that it helps them act more virtuously. They praise Holiday for condensing some of the Western world’s most valuable wisdom into a form that’s quick and easy to digest. Supporters also enjoy the storytelling style and examples from history that Holiday uses to present his ideas.

Common criticisms of the book include the fact that it’s philosophically shallow, especially compared to other popular contemporary books on Stoicism. The book is mostly made up of variations on the same idea. Additionally, many complain that Holiday doesn’t offer enough actionable advice—he tells you to change your perspective on obstacles without fully explaining how to do so.

Commentary on the Book’s Approach

The Obstacle Is the Way isn’t intended to be a comprehensive guide to Stoicism—it’s a self-help book intended for a broad audience. Holiday himself admits to simplifying Stoic ideas to make the book more accessible. As such, the book at times tends to appeal more to the reader’s emotions than their sense of logic. Holiday prefers to present ideas to the reader and hope they resonate rather than to convince the reader of his argument.

Commentary on the Book’s Organization

The Obstacle Is the Way is divided into three parts: “Perception,” “Action,” and “Will,” which Holiday argues are three foundational domains you must master to solve problems like a Stoic. 

Holiday’s decisions on which chapters to place in each section can appear arbitrary. Some of the chapters Holiday places in the “Action” section occur internally (“Practice Persistence,” “Channel Your Energy”), while some of the “Perception” and “Will” chapters involve tasks that could be placed on a to-do list (“Think Differently,” “Anticipation (Thinking Negatively)”). Additionally, the line between “Perception” and “Will” gets a little blurred, as they both involve perceiving negative situations in an empowering way.

The Obstacle Is the Way: Review & Critical Reception

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Here's what you'll find in our full The Obstacle Is The Way summary :

  • Why you should think of any obstacles as opportunities
  • How Stoicism can show you the way to overcome challenges
  • How Theodore Roosevelt's struggle with asthma prepared him for future struggles

Darya Sinusoid

Darya’s love for reading started with fantasy novels (The LOTR trilogy is still her all-time-favorite). Growing up, however, she found herself transitioning to non-fiction, psychological, and self-help books. She has a degree in Psychology and a deep passion for the subject. She likes reading research-informed books that distill the workings of the human brain/mind/consciousness and thinking of ways to apply the insights to her own life. Some of her favorites include Thinking, Fast and Slow, How We Decide, and The Wisdom of the Enneagram.

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