These are some of the books and essays that have stuck with me the longest. They seem to hold wisdom.

Civilization

• Pace Layering: How complex systems learn and keep learning – Stewart Brand
• The Clock of the Long Now: Time and Responsibility  – Stewart Brand
• The Carrier Bag Theory of Fiction – Ursula K. Le Guin
• Wilding – Isabella Tree
• The Overstory – Richard Powers
• The Big Here and Long Now – Brian Eno
• A short history of progress – Ronald Wright
• The Black Swan – Nassim Nicholas Taleb
• Thinking, Fast and Slow – Daniel Kahneman

Technology & Making

• Succession – Sep Kamvar
• Mastery & Mimicry – Sep Kamvar
• Make space for beauty – Sep Kamvar
• The Poet and the Computer – Norman Cousins
• Education of a Programmer – Terry Crowley
• The Nine Billion Names of God – Arthur C. Clarke
• Shop Class as Soulcraft – Matthew B. Crawford
• Reality has a surprising amount of detail – John Salvatier
• Creative Selection – Ken Kocienda
• We don’t sell saddles here – Stewart Butterfield
• Work on stuff that matters – Tim O’Reilly
• Maker’s Schedule, Manager’s Schedule – Paul Graham
• A Pattern Language – Christopher Alexander, Murray Silverstein, and Sara Ishikawa
• Cradle to Cradle: Remaking the way we make things – Michael Braungart & William McDonough
• Wabi-Sabi: for Artists, Designers, Poets & Philosophers – Leonard Koren

Philosophy

• Archetypes revisited – Craig Mod
• Barbarian Days: A Surfing Life – William Finnegan
• Tao Te Ching – Lao Tzu, translated by Ursula K. Le Guin
• The Snow Leopard – Peter Matthiessen
• Where the sidewalk ends – Shel Silverstein
• Manifesto: The Mad Farmer Liberation Front – Wendell Berry
• A Wizard of Earthsea – Ursula K. Le Guin
• The Fountainhead – Ayn Rand

It is easy for me to imagine that the next great division of the world will be between people who wish to live as creatures and people who wish to live as machines.
Wendell Berry