I like to parse reading lists. Here is a collection of reading lists I like, and also a curated set books (limited to about 50) that I found insightful, useful, or just plain enjoyable. Many of these I actually consumed as audiobooks.

WORK IN PROGRESS

Reading Lists

Alan Kay
Ray Dalio
Bill Gates

Biography & Rumination

Surely You're Joking, Mr. Feynman! (Adventures of a Curious Character) by Richard P. Feynman
Benjamin Franklin - An American Life by Walter Isaacson
The Innovators by Walter Isaacson
Hitch 22 and Letters to a Young Contrarian by Christopher Hitchens
The Invention of Nature by Andrea Wulf

Cognition & Psychology

Thinking, Fast and Slow by Daniel Kahneman
Emotional Intelligence by Daniel Goleman

History & Philosophy

Sixteen Satires by Juvenal
Sapiens and Homo Deus by Yuval Noah Harari
Waking Up by Sam Harris
Enlightenment Now and The Better Angels of our Nature by Steven Pinker

Technology

Artificial Intelligence: A Modern Approach by Stuart Russell and Peter Norvig
Deep Learning by Ian Goodfellow, Yoshua Bengio, Aaron Courville
Humans Need Not Apply by Jerry Kaplan

Energy, Physics, Fundamentals

The Grid by Gretchen Bakke
Our Mathematical Universe: My Quest for the Ultimate Nature of Reality by Max Tegmark

Management & Business

Principles by Ray Dalio
The Effective Executive by Peter Drucker
High Output Management by Andy Grove
Poor Charlie's Almanack by Charles T. Munger
Fooled by Randomness by Nassim Nicholas Taleb
The Intelligent Investor by Benjamin Graham

Design, Art, Visualisation

Illumine by Garry Fabian Miller
Envisioning Information and Beautiful Evidence by Edward Tufte
Phaidon Design Classics I-III

Fiction

Fantômas by Marcel Allain & Pierre Souvestre
Catch-22 by Joseph Heller
Slaughterhouse-Five by Jurt Vonnegut
Smiley's People by John le Carré