The Obstacle is the Way, by Ryan Holiday. Book report #10 (2021)

The Obstacle is the Way, by Ryan Holiday. Pub 2014

A medium-deep dive into philosophy – specifically, stoicism – this book was recommended by Kielyn Marrone, who I follow on social media after watching her the TV show “Alone” (where contestants are dropped off in the middle of nowhere and have to survive longer than other participants in order to win $1M). Kielyn stayed 80 days in the near-Arctic (shores of Great Slave Lake from mid-September through December). Watching her catch her first fish from the frozen lake was one of the most enjoyable moments on TV ever. She was the third last participant, and everything about her was intriguing and inspirational, including her frequent mentions of stoicism. On her Facebook page, she recommends this book; coincidentally, one of my current mentees is reading this book series by Ryan Holiday, and mentioned it during one of our earliest sessions. I took that as a sign.

At first, I just dipped in a toe. I have previously attempted to read Marcus Aurelius’ Meditations, never making it very far. This started back in high school, after reading a quote from him in The World According to Garp. So for more than 30 years I’ve had a copy of that book in one form or another waiting to be read, but with very little actual progress. For Obstacle, I started with an audiobook, to see if that would help get me into the work. It certainly did. I enjoyed it so much that, after just half of the book I pulled out my hard-copy and dove in, reading it from start to finish in just a few days (being on vacation helped a lot). 

The book begins with Aurelius as the sort of compilation or zenith of stoic philosophical writing, but includes many other ancient and more modern philosophers and figures who personify elements of stoicism. Some are familiar stories and people (Lincoln, Edison, Thatcher), others less familiar but still inspiring, embodying the principle at the heart of the book: the things that are in your way are exactly the things you need to be tackling to move forward, and the lessons you learn from each attempt to move or surmount or submit your obstacle become lessons for your life. In other words, what doesn’t kill you makes you stronger, but also: to strive, to seek, to find, and not to yield.

Throughout the stories and philosophies you can see elements of currently trendy approaches – minimalism (many of our problems come from having too much, being paralyzed by choice), mindfulness (we don’t get to choose what happens to us, just how we feel about it), personal responsibility (no one else is to blame when we throw in the towel), humility (the obstacle doesn’t care about you), equality (you can always try, but success is never guaranteed or owed), persistence (the goal should be progress, not perfection). 

I think like self-help or other similar books, the text includes many tru-isms and statements that, when you first read them seem statements of the obvious. But this is not a self-help book in the sense that it give no specific directions: try this, 5 steps to a better you, etc. Instead, it presents, in bite-size pieces – short, focused chapters – stories and messages that cannot help but drive introspection and personal challenge to do and be better. 

I’m looking forward to reading the remaining books in the series (Ego is the Enemy, Stillness is Key), but likely after a bit of a break. And I may take another stab at Aurelius (perhaps I’ll start with audio again and see what happens). Regardless, I found this book to be meaningful, insightful, challenging, and delightful.

Fate: hanging on to it, but highly recommend it. 

25 – an author I’ve never read before
30 – philosophy/religion