Book Reviews, Reviews

The Obstacle is the Way by Ryan Holiday


Since it was Ryan Holiday’s “This is How I Work”) and book review mailing list that inspired my self imposed challenge to read and review a book a week (on average) this year, it seemed only fair that I read one of his books. The Obstacle is the Way was published while I was reading Letters From a Stoic, so the timing was perfect to dig into it next.

When I read The Four Hour Work Week and Antifragile, both books seemed a little infomercialy. As if they were like those videos advertised on late night TV where the maker promises you’ll learn how to get rich quick by following their X easy steps, which turn out to be steps in how to get rich making and selling other get rich quick videos. I think both of those books have some good information in them, and I’m glad I read them both. But they felt at least a little slimy, for lack of a better word. I was expecting more of the same from this book, and I was genuinely surprised that I never got that feel from it.

Maybe it’s because I had just finished Seneca, so I read this more like philosophy than “self-help.” Or maybe it’s because I didn’t get the impression that this book was trying to sell me a bill of goods (other than the text itself). Holiday comes off less like a salesman and more like a mentor, which I really appreciated.

Another thing I really appreciated about the book was that it felt like a complete formula. The Four Hour Work Week (as I remember it; it’s been several years since I read it), and Antifragile both had passing mentions that you shouldn’t expect everything to work out right away and that perserverance will help you make it through the rough patches. But The Obstacle is the Way actually explained what that meant, and how it could work (emphasis on could).

I also found the anecdotes about other people actually using their obstacles to their advantages really compelling. In fact, it ended up coming up in conversation the day I started reading the book.

I mentioned in my review of Letters From a Stoic that it was my fourth-most highlighted book, and that Rational Optimist was #1. I haven’t had a chance to redo the math now that I’ve finished this but I expect it will break the top 3. I definitely expect I’ll be reading this book again. I can’t think of a more ringing endorsement than this: the day I finished reading it, I immediately bought a copy for someone who I thought would benefit from reading it.


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