What follows is not a list of my favorite books & articles -- indeed, many of my most beloved pieces of fiction have been left off. Rather, the primary criteria for inclusion on this list is that the piece is "interesting", from an "ideas" perspective. I don't necessarily endorse or even agree with all of the ideas presented, but I find them all thought-provoking in one way or another.
I find myself tempted to arrange the following into categories for easier consumption, but in attempting such an exercise, I run into the problem where most of these works are interesting precisely because they resist categorization -- or rather, their nominal categorization is limiting, obscuring the broad applicability of their ideas which, I believe, in part makes them so interesting to me.
Thus, for now, they are presented in no particular order.
Gödel, Escher, Bach - Douglas R. Hofstadter
How Complex Systems Fail - Richard I. Cook, M.D.
Destruction and Creation - Col. John Boyd
Boyd - Robert Coram
Guns, Germs, and Steel - Jared Diamond
The Tangled Tree - David Quammen
The Elephant in the Brain - Kevin Simler and Robin Hanson
An Astronaut’s Guide to Life on Earth - Col. Chris Hadfield
On Bullshit - Harry G. Frankfurt
Thinking, Fast and Slow - Daniel Kahneman
The Organization Man - William H. Whyte
The Nature of the Firm - R. H. Coase
Siddhartha - Herman Hesse
Zen and the Art of Motorcycle Maintenance - Robert M. Pirsig
The Federalist - Alexander Hamilton, James Madison, and John Jay
Moneyball - Michael Lewis
The Cathedral and the Bazaar - Eric S. Raymond
A Little Big Idea Called Legibility - Venkatesh Rao
A Lifetime of Systems Thinking - Russell Ackoff
The Agile Manifesto
Starship Troopers - Robert A. Heinlein
The Tragedy of the Commons - Garrett Hardin
Utilitarianism - John Stuart Mill
The Fountainhead - Ayn Rand
Bored People Quit - Michael Lopp
The Update, The Vent, and The Disaster - Michael Lopp
Lenticular Design - Mark Rosewater
Declaration of Digital Independence - Larry Sanger
The Extraordinary Leader - John H. Zenger & Joseph R. Folkman
Walden - Henry David Thoreau