The Obstacle Is the Way

This isn't much more than a superficial repackaging of stoicism combined with some semi-interesting anecdotes and a whole lot of trite motivational affirmations. The book is written in the style of Holiday's mentor, Robert Greene, but where Greene does something rare and surprising by compensating for his lack of personal experience with deep and compelling research, The Obstacle is the Way falls flat. The anecdotes are common and superficial and their ties to Stoicism feel tenuous at best. Then, to make it worse, rather than allowing the stories and quotes from the stoics to speak for themselves, they are always followed by explicit and repetitive advice that just constantly restates the one idea that yes, the obstacle is the way.

I really like Ryan. I think he's done some great work elsewhere. I have heard him interviewed and he is a sincere and positive guy. This book feels rushed and incomplete though.