I’ve gleaned a lot of wisdom from these. Some are just plain entertaining.

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Fiction
The Things They Carried by Tim O’Brien
The People of Paper by Salvador Plascencia
Middlesex by Jeffrey Eugenides
Last Evenings on Earth by Roberto Bolaño
Bluebeard by Kurt Vonnegut
Franny and Zooey by J. D. SalingerDrama
Waiting for Godot by Samuel Beckett
Rosencrantz and Guildenstern are Dead by Tom Stoppard
The Merchant of Venice by William ShakespeareEssays
Eating the Dinosaur by Chuck Klosterman
What the Dog Saw by Malcolm GladwellBusiness/Self-Help
The War of Art by Steven Pressfield
The 22 Immutable Laws of Marketing by Al Ries and Jack Trout
How to Fail at Everything and Still Win Big by Scott Adams
The Obstacle is the Way by Ryan Holiday
Antifragile - Nassim Nicholas Taleb