Infinite Jest

This book may seem out of place in a list of psychologically-minded self-help recommendations. And it is long, and hard to read. Don’t even get me started on the use of end-notes in a work of fiction. But it is quite simply one of the best books written in the past 100 years and it is all about people who have gotten stuck, trapped by habit or circumstance, and are yearning for a way to find meaning in life.

To me, this book is a self help book because it is written so powerfully (in a not-so-distance fictional future) that… show more.

I know, I know, it's supposed to be pretentious and self-negating to talk about the great DFW now. But that doesn't change the fact that in his imagining an America where everyone is so mesmerized by a piece of entertainment that they've lost their minds... well, dude imagined the iPhone. Also, the Year of the Depends Adult Undergarment.

It's gigantic and meandering and a slog at times, but no single novel predicted our hellscape better than this one. Sorry. That's prophecy.

One of the best criteria for a book to read in prison is length. Sometimes it’s hard to get more books quickly, and since some facilities have limits on how many books you can have at one time, the longer the better. At 1,079 pages, David Foster Wallace certainly delivers on that front. In the free world, that might seem like a bit of a slog but the book is also funny and has some nuggets of wisdom about addiction and recovery that resonated with me when I read it a decade ago during a brief stint in solitary confinement.

DFW turned tennis into math and art throughout his essays and this, his magnum opus, a massive and funny and challenging novel that everyone says they've read, but didn't really. Not underrated, not overlooked, but a sure-to-be timeless work where philosophy, comedy, and literary genius intersect at a tennis academy. 

Infinite Jest changed everything for me. Its fragmentation, and the way it sets a dozen plots and subplots in orbit around a single “quest object” (a mysterious video that is purportedly so entertaining that to watch it is to be rendered catatonic and die), makes the reader an active participant in assembling the book’s meaning. This is the way I love to read, and I’m trying to create a similar effect in my own writing. I also think that Wallace was one of the greatest sentence writers to ever hold a pen, and the blistering syntax of Infinite Jest gives… show more.