Technically speaking, I've read Zen and the Art of Motorcycle Maintenance 1.5 times. The second time through was much more important than the first.
I started this book over two years ago on an unusually warm spring day at my in-laws' house (I remember that because I managed to get sunburned that day, which is impressive for May in Minnesota). I was immediately intrigued by this book, but I constantly felt that its philosophy was going over my head. I read more than half of the book on my first attempt, but through no fault of the book's, I started reading it irregularly which eventually lead to me putting it down for a few months. Picking it up after that long of a break proved unsuccessful, so it went on my shelved list for a little while. I'm glad it did; I wasn't quite ready to take it on yet.
I decided to start the book again from the beginning nearly two years later. This was long enough for me to forget most of its contents, but still recognize things with some familiarity. I loved my second reading of this book: I took things slower, I re-read pages occasionally, and felt a much deeper appreciation of its content. I still can't pretend to have comprehended even half of its material, but I felt like I was much closer the second time.
Reading the second half, which was still new to me, proved to be as challenging as the first half was on my first reading. I powered through it though and did my best to follow the deepening philosophical context.
Even after finishing it, this book remained on my mind, which I'm sure was intended. I think my third reading of it, sometime in the future, will probably be the best.
A few recommendations I have to those of you considering to read this book:
1: If you have the 25th Anniversary Edition, like I do, don't read the opening chapter "Introduction to the 25th Anniversary Edition" which was written by the author. You've probably seen this as a common pattern with republished books, but if you haven't, introductions in these republished editions are usually intended for people who are re-reading the books many years later, so the author speaks to you as if you already know what happens at the end. If you read it without context, you'll not only be confused, but also have important experiences spoiled for you. Skip that chapter, and come back to it once you've finished.
2: It might help to treat this book like you're being graded on your comprehension of its material. (Hopefully that doesn't kill what the author intended...). Several times I found myself unable to follow some of the material, most likely because of the author's deep experience in philosophy. In some books, I'd say "just push through it" and get back to comfortable territory, but in this case, I think it's worth re-reading pages until you start getting the idea.
3: In the 25th Edition version of this book, the typeface is significant. Several times I noticed sections of the book were suddenly in a sans-serif font (the rest of the book is serif), and I thought it must have been due to an issue when reprinting the book or something. Nope, it's a deliberate storytelling mechanism. Pay attention to it.
4: This is definitely a philosophy book at heart. While not required, you might find it helpful to study a little introductory philosophy before digging into a book like this. I decided to read The Consolations of Philosophy by Alain De Botton as a primer, and although it wasn't specifically relevant to the book, I think it helped get me in the correct frame of mind.
5: If this type of book appeals to you, you might enjoy Gödel, Escher, Bach: An Eternal Golden Braid by Douglas Hofstatder. I happily admit that I probably understood a small fraction of the material presented in GEB, which was definitely the most challenging non-fiction book I've ever read, but time-after-time while reading Zen and the Art of Motorcycle Maintenance I felt flashes of insight from my experience reading GEB. There's a lot of crossover between these books.
6: Something I haven't yet done but might be a good idea: After reading the extra material at the end of Zen and the Art of Motorcycle Maintenance, I learned about a book called Guidebook to Zen and the Art of Motorcycle Maintenance by Ron Di Santo and Tom Steele. This book was approved by Robert Pirsig and is the result of years of study into the philosophy of Zen and the Art of Motorcycle Maintenance. I haven't read it, but I'm going to add this to my to-read list.
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