Book Review: 'The Obstacle is the Way' by Ryan Holiday

By Roger Dooley

http://www.forbes.com/

June 4, 2014

Here’s a quick quiz. Which would you prefer to read, given these choices?

1. A philosophy book focused on the ancient concept of Stoicism.
2. A short, inspiring book packed with stories describing how famous leaders and entrepreneurs achieved success by pragmatic action in the face of overwhelming odds.

Author Ryan Holiday has cleverly disguised the first choice in the guise of the second in his new book, The Obstacle is the Way: The Timeless Art of Turning Trials into Triumph.

In fact, this book reads far more like a book of practical business advice than a dusty philosophy tome. Holiday is a media strategist, Director of Marketing for American Apparel, and the author of the best selling book, Trust Me, I’m Lying: Confessions of a Media Manipulator.

What makes this relatively short book so engaging is that it is packed with stories. Each brief chapter focuses on a principle, usually illustrated with at least one example of a leader who employed that principle to overcome adversity.

One chapter, “Follow the Process,” starts with a description of Coach Nick Saban’s unprecedented achievements base, in large part, on his process. Instead of focusing on novel strategies or motivational speeches, Saban and his teams grind forward, always striving to exist in the present moment. Finishing is the focus: finishing workouts, plays, drives, games, and so on. This small-picture emphasis leads to big-picture success.

The Power of Negative Thinking
CMOs and business leaders of all types will find the chapter titled, “Anticipation (Thinking Negatively),” relevant. It dives into the “premortem” concept – before you roll out a campaign or project, the responsible group meets to discuss why it failed. Members suggest reasons for failure, with the hope that by enumerating them at the start they can be avoided.

Although the practice of conducting a premortem meeting seems like a recent innovation, Holiday points out that this concept dates back to the stoics. They called itpremeditatio malorum, or premeditation of evils. (Don’t worry, references to dead languages are hard to find in Obstacle.)

What Stoicism Isn’t
In popular English usage, “stoic” has taken on the meaning of being without emotion, or even passive. Holiday explains that while the Stoic philosophy does indeed discourage pointless displays of potentially distracting emotion, it is, in fact action and results-oriented. Rather than passively enduring suffering, a true Stoic evaluates the situation in a realistic and pragmatic way, then attempts to solve the problem.

When faced with an obstacle, many people might quit, or spend energy complaining about it. Leaders and innovators find a way around, over, or through the obstacle, often achieving greater success than they would have otherwise.

Sometimes obstacles can be made to defeat themselves. In his quest to change India, Gandhi had no power and the ruling hierarchy had immense power. So, he deliberately violated a minor law prohibiting collecting salt from the sea, knowing that an attempt to bring the might of the state down on him to enforce that law would make the rulers look ridiculous.

Holiday, in a chapter titled, “Get Moving,” points out the value of taking even small steps toward your goal. We all know Amelia Earhart for her solo flying exploits, but how she got her start is less well known. Unable to make a living as a pilot, she took a job in social work. Then, as a publicity stunt, a group offered to fund the first transatlantic flight by a woman with her on board. Even though she wouldn’t be allowed to fly the plane, wouldn’t be paid, and was the second choice for the role, she accepted. By refusing to be offended, she seized the opportunity that was offered and launched her illustrious career.

The Obstacle Is The Way is an inspiring read for anyone faced with adversity – and who isn’t?

Most of us aren’t faced with the kind of obstacles faced by Abraham Lincoln, Martin Luther King, or George Patton. But, reading their stories puts our everyday challenges in perspective and makes them seem surmountable.

We can all benefit from the Stoic emphasis on pragmatic decision-making, flexibility in the face of changing conditions, and seeing the world as it really is. Business people at any level will find Obstacle helpful, but I think it’s particularly appropriate for new graduates. If they can internalize even a part of this philosophy, they and those they work with will benefit greatly.

If you spend a few hours with The Obstacle is The Way, you may save years of future angst.

Roger Dooley is the author of Brainfluence: 100 Ways to Persuade and Convince Consumers with Neuromarketing (Wiley, 2011). Find Roger on Twitter as@rogerdooley and at his website, Neuromarketing.