As I mentioned in my discussion of How to Let Things Go, I would be writing about Ryan Holiday’s book The Obstacle is the Way very soon. Many of the topics covered in each of these books are very similar. Both discuss the importance of perspective and controlling only what we can control, which is our actions to what happens. Both either directly or indirectly advise that we should have grace and forgiveness of ourselves when we make mistakes and not dwell on those mistakes with regret and pain, but learn from them and turn them into future actions.
The topics discussed in The Obstacle is the Way are rooted in history and philosophy. Holiday does an excellent job of including real-world examples for most of his lessons to illustrate how the teaching can be seen in practice. These aren’t made-up ideals, but rather real-world lessons that many of us have been shielded from in one way or another.
While the lessons in the book are truly valuable, I found myself really struggling to get through the book. At times it was very slow and felt like a five-page chapter would take an eternity to get to the point. I’m not an author and have no business criticizing anyone who has written a book, so I want to be clear that I am not criticizing Ryan Holiday, his book, or the lessons taught in the book. However, I feel that I owe it to the readers of this website to explain where I’m coming from and how I personally struggled to digest the content of this book. That is all.
I tried reading this book around the Summer of 2023. I had just been laid off from my job and found myself questioning everything. I felt like I was on a boat going down the West Virginia rapids and had no paddles, no life preserver, and no one in the boat to help me. I was lost and stuck at the whims of the rough rapids I was desperately trying to navigate (metaphorically speaking).
At that time, when I tried reading this book, I wasn’t able to get very far. I wanted to. But I kept feeling like the author was stating all of these clear observations and lessons, but giving no tangible methodology for how us normal folks can overcome these challenges. Eventually, I put the book aside and refused to go any further.
This time around, I tried to keep an open mind. I remembered feeling this way and I was determined to try to find where the nuggets of wisdom lay and how the author would present a methodology for people to use these lessons in their everyday lives. After finishing the book, I will be honest that I still feel this missed the mark to some degree. The book excels in teaching a lesson and showing how someone in history or philosophy used this lesson in actual practice so the reader has a working example. But if it were that simple, I feel like most people would have done this already. Right?
Hear me out. If this book doesn’t provide a strong action plan, but primarily teaches the lesson, provides an example, and metaphorically says “Now you do it”, then this would imply that we all were just missing being informed about the lesson. Our education was lacking, so now that we know about it we should be able to do it. Well, I know how to say certain phrases in Spanish, but I am 100% not fluent in that language and can’t hold a conversation in Spanish – I took two years of Spanish in high school; I took two Spanish courses in college; I attempted Rosetta Stone countless times; I have a wife and in-laws who speak Spanish fluently; and I still struggle with this.
To me, education is the first roadblock. But where this book needs to go to take this to the next level is in presenting an action plan that people can use to put this into practice every day. To be fair, this may already exist somewhere. I haven’t researched it at all. In this article, I am focused primarily on how I interpreted and digested the content of the book. So if this already exists, please leave a note in the comments or feel free to email me at greg@ultimatesportstalk.com. I legitimately am interested in learning more.
What I do know is that Ryan Holiday is a prolific author and there are many more books that he has written. This will not be the last book that I read. I am actively in search of how he teaches us to leverage these lessons and put them into action every single day.
I will end this by clearly saying that reading this book was not a waste of time. It enabled me to consider some of my past experiences, how I’ve reacted at times, and where I am lacking in many areas. This alone was well worth it. To use another analogy, the light is now on in the room, and I can look around. And for that, I am grateful.
