The Obstacle is the Way: The Timeless Art of Turning Trials into Triumph (2014) by Ryan Holiday is a book about overcoming apparent setbacks and by turning them to our advantage. It’s not exactly a book about Stoicism but it does contain a great many references to Stoicism, which reinforce the central message that every adversity is potentially an opportunity.
Ryan was the keynote speaker at the Stoicon 2016 conference in New York, where he talked about the profound influence that reading the Stoics had on his life. The book he subsequently co-authored with Stephen Hanselman, The Daily Stoic, focuses exclusively on Stoic wisdom, presenting quotations from the classics for each day of the year.
Indeed, the title of The Obstacle is the Way is inspired by a famous quotation from The Meditations of Marcus Aurelius, which reads:
The impediment to action advances action. What stands in the way becomes the way.
This is a quote from the Gregory Hays translation of Meditations 5.20, which Marcus begins by reminding himself that in one respect other people are of concern to us and that we have a duty to help them, alluding to the Stoic concept of oikeiôsis, or identifying with the welfare of others. In another respect, though, he says other people are as indifferent to us as sun or wind, or wild animals, being external to our own mind and volition. We shouldn’t place too much importance on what they think of us, as long as we’re aiming to do what’s right and acting wisely.
Ryan’s book contains a plethora of anecdotes about historical figures who have persevered in the face of social and material obstacles, under conditions that would make many people abandon hope. In that respect, it stands in a venerable tradition of self-help books, one that goes back indeed to the Victorian classic Self-Help (1859) by Samuel Smiles. It also harks back, as Ryan notes, to Plutarch’s Lives, the express purpose of which was to be simultaneously both an ethical and historical treatise by focusing on what can be learned from the characters and virtues of numerous great men.
There’s plenty of good advice in The Obstacle is the Way; it’s an interesting and entertaining read. It will perhaps also inspire many people to study Stoicism in more depth and also to explore the range of psychological skills and strategies used by the Stoics to overcome such obstacles, and maintain their equanimity in the face of adversity. That’s something I’ve written about but unfortunately I still don’t think there’s a really good popular introduction that covers the range of Stoic doctrines and practices.
I was pleased that the book made me realise the beautiful simplicity and appeal of the story of Demosthenes, the famous Athenian orator. I told my five-year old daughter this tale after reading about him in the book, and she made me tell it to her again and again, two or three times the same day. There were many stories from American political history that I wasn’t very familiar with, which were also fascinating to read.
The most important thing about the book, though, is its message that a formula for turning obstacles into opportunities can be learned from the examples of these great (and in some cases not so great) men and women. From Marcus Aurelius to Ulysses S. Grant, Thomas Edison, Theodore Roosevelt, Amelia Earhart, Erwin Rommell, Abraham Lincoln, and Barack Obama. Most of these individuals had their strengths and weaknesses, of course. (As a Scot, my flesh crawls at the sight of Margaret Thatcher’s name, and Steve Jobs was a notorious bully who exploited his own friends and workers in ways that many people would balk at as unethical.) However, what Ryan’s doing is trying to model specific examples of resilient behaviour and attitudes from these recognisable figures, not their whole lives and characters, which are inevitably a mixed bag.
That’s something I think he’s achieved admirably and I’m very pleased the book has already become so successful. Every day, it seems to bring more people into the Stoic community, who say they “got into Stoicism” after reading The Obstacle is the Way, and now have a thirst to learn more. That’s a good thing. As the founders of the Stoa taught: the wise man has a duty and natural calling to write books that help other people. Though none of us are indeed wise, we can help others by writing about the lives of people who exemplify virtues to which we might all aspire. That’s why I think this is a book worth reading. It gives people hope that they might be able to learn how to live like that, with admirable resilience and tenacity, and it surely motivates them to engage in self-improvement in the same direction.