With The Obstacle Is the Way you only have to say aloud the title, and the whole premise of the book is revealed. Ryan Holiday isn’t trying to hide his main argument which is this: we can’t control chance, luck, or the world, but what we can do is control how we react to them. The next bit is more complicated (not really), often enough we are the ones ourself who are the obstacles in our way. That our reaction might impair our ability to survive the hardship. When we think of hardship as an opportunity, we might gain something new or meaningful in our life. That is the book in a nutshell.
Ryan Holiday goes over the basic arguments of stoicism, drawing examples from history, modern life, and from a convicted prisoner to the world leaders. He paints with the examples of how they acted when facing difficulties and how such obstacles changed their lives, bringing more than they could have understood at the beginning of their journey, always concluding to a happy ending. And this is where the criticisms towards the book step in. The book makes it sound as if anyone can get past whatever they are facing if they alter their perspective, persevere, and value what they have. Not everyone sees every blow to their life as an opportunity. But in defense of the book, the argumentation is in line with stoicism which has always been a practical philosophy and not in the University weird twisted way of practicality, but as real advice to real situations. But I agree with the criticism there is something missing in the book and I will get to that.
The book’s problem isn’t the oversimplification of stoicism or how to face obstacles. I think it’s the thinness of the book. What I mean with this is that yes the historical examples were good and informative, but they left me wanting for the writer’s own voice and experiences. After listening to the book, I listened to the writer’s interview, talking with his friend, and I gained more insight from that talk than this book. The message came personal. I can understand the reason the writer didn’t lay his life for the world to read and let others dismiss his experiences due to his young age. For me, that wouldn’t have muted the point. Age is not an indicator of someone’s ability to understand the world. But some might see things differently.
The other issue I think it has even when I agree enough with the points made is the disregard for the obstacles themselves. What I mean is, that yes sometimes the most horrible situation you can imagine can be the greatest opportunity there is, but having lived through one that made me devalue and hate myself, broke my spirit and mind, and left me a crying ball on my bed nothing is ever that simple. Yes, something wonderful came to be after that, but it wasn’t easy nor it came for free. I lost my former self. And if someone says they came out of their obstacle unscathed, then they lost nothing which mattered. The point is when things are so bad words like go on, there is a silver lining or buckle up doesn’t help. And I would have liked the book to acknowledge the cost of a loss as it is a big part of any obstacle. This doesn’t mean I don’t agree that our reactions matter, that sometimes something good comes out the worst, that we can’t stop and give up, but I wouldn’t understand this if my spirit wasn’t broken and I pieced myself together. This is not a bad book. It can and should inspire others to act or even get to know stoicism. But, this is my but, there could have been more. Something deeper underneath the steps and historical recounts. Maybe a greater acknowledgment of the pain and torment we face. That those can sometimes overpower even the strongest of us.