Book Review: The Obstacle is the Way


By Ryan Holiday

Portfolio Press, May 1, 2014, 224 Pages

Hardcover $14.95, electronic addition $9.99, audible version $4.49

In a Nutshell: “The Obstacle is the Way” shows with its philosophical anecdotes and historical references that there is a right way to approach the inevitable adversity that comes our way.

Who’s it for? This is a book with broad audience appeal. “The Obstacle is the Way” makes a good gift for recent college graduates or members of your work team.

Quote from Author: “Blessings and burdens are not mutually exclusive.”

Ryan Holiday is a marketer, entrepreneur, and the author of two previous marketing books. In his third effort, “The Obstacle is the Way,” Holiday boils down the critical parts of dealing with life’s inevitable challenges. Absent is the hard science one would expect with such a topic. As an alternative, Holiday relies on stories and his analysis of others who persevered in bleak circumstances.

“The Obstacle is the Way” draws its title from a quote in “Meditations,” a series of readings written by the Roman emperor Marcus Aurelius: “The impediment to action advances action. What stands in the way becomes the way.” The idea of looking strategically at a crisis as an opportunity is hardly new, although Holiday offers up plenty of examples that are inspiring presented in a short, concise chapters.

Holiday begins by analyzing how our perceptions are a key factor in how each of us responds to obstacles in our lives. Living in the present allows us to not be sidetracked by the negative “what if” scenarios that haven’t yet occurred. He describes what many would term emotional intelligence or the ability to control both or body and mind. For example, Astronaut John Glenn’s trained ability to keep his heart rate under 100 beats per minute for an entire day while orbiting the earth.

Holiday describes discipline as the directed actions that analyzes both what is happening now, while also strategizing to reach the ultimate goal. “Step by step, action by action, we’ll dismantle the obstacles in front of us.” He uses the great Greek orator Demosthenes as the example of someone that was born with a speech impediment but studied other great speakers and practiced for many decades before perfecting his skills.

A chapter titled: “Build Your Inner Citadel” tells the story of Theodore Roosevelt who, despite being born into affluence, overcame a severely weak body and asthma to become the strong figure for which he is revered. In this chapter and throughout the book, Holiday references ancient Greek philosophy of Stoicism, or living rationally in accordance with nature.

The follow-up chapter “Anticipation” explains that exploring worst case scenarios as a way to anticipate all possible outcomes and “accommodate ourselves to any of them” is a useful exercise. In other words, post-traumatic growth is much better than Post Traumatic Stress Disorder.

Reading through this book was enjoyable and, at 224 pages, did not take long. Holiday does an admirable job of storytelling and organizing his rationale. Since its release in in 2014, “The Obstacle is the Way” has become popular in many circles. The book’s fans include Arnold Schwarzenegger, LL Cool Jay, and the New England Patriots football team. In fact, “The Obstacle is the Way” was required reading for team members prior to the Patriot’s 2015 Super Bowl victory.

In the end, however,  “The Obstacle is the Way” is heavy on inspiring tales and profiles but fails to deliver tangible takeaway techniques. Like any good marketer, author Holiday provides plenty of sizzle but this steak is just a bit undercooked.

Chris Wendel is a business consultant and commercial lender with Northern Initiatives, a community development financial institution based in Marquette. Wendel resides and works in Traverse City and can be reached at