My review of “The Obstacle Is the Way” by Ryan Holiday

My review of “The Obstacle Is the Way” by Ryan Holiday

Continuing my current kick of studying the philosophy of Stoicism, Ryan Holiday’s The Obstacle Is the Way is a superb primer on the Stoic principles. For one thing, at 224 pages, it is less than half the size of the last book I read on the same theme, Derren Brown’s superb Happy. This is by no means a bad thing, however, for while Brown’s book delves into the history of Stoicism and man’s eternal search for that which will make us happy, Holiday’s is a quicker, lighter read, but one that packs a hell of a punch.

The gist of the book is that if one applies the principles of Stoicism carefully and mindfully, then no matter what happens (good, bad, or indifferent) then it becomes possible to deal with the highs, lows, and plateaus of life with equal poise and calmness. Obstacles, Holiday posits, represent opportunity, and should be welcomed rather than feared, for they offer us chances to grow and become more than we currently are.

There’s nothing really new here, and I say that without being critical. The tenets around which Holiday builds his case are thousands of years old, being drawn primarily from Epictetus and Marcus Aurelius, among others. The great success of the book is its ability to distill these concepts down into usable, everyday ways of thinking which can benefit each and every one of its readers, if they are disciplined enough to apply them to their own lives. It points out (quite correctly) that the problems faced by the average Greek or Roman citizen were, at their core, fundamentally no different than the ones that vex us today, for they are based upon the same old negative emotions: fear, jealousy, anxiety, greed, a desire for celebrity, and so forth. Marcus Aurelius, one of Rome’s five so-called “Good Emperors,” wrestled with all these issues and more on a daily basis, and used Stoicism in order to successfully conquer them…and himself. There are very good reasons why Meditations is still read so widely (and re-read so frequently) today. I have returned to the book regularly ever since I discovered it as a teenager, and will probably do so for as long as I live. These truths are timeless, and invaluable.

Holiday refers to the Stoic philosophy as “an operating system for living,” which seems very apt in this digital day and age. If that is indeed the case, then The Obstacle Is the Way serves as an introductory manual for that operating system, a primer that helps one get to grips with how it works. Some of the complexity and nuance may be left out or abstracted, but the thrust of it is covered succinctly, with plenty of easily understandable contemporary examples to clarify things.

I highly recommend this book to anybody who could use a little help in dealing with the stresses and strains of everyday living…and at the end of the day, isn’t that all of us?

Posted on: December 13, 2016Richard Estep

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