1. Books that provide a window onto an interesting piece of the world
   • Examples: Hillbilly Elegy, Courtroom 302, The Power Broker
2. Books that present surprising case studies, events that force the question, “What does it imply about the world, that X could happen?”
   • Examples: The Idea Factory, Extraordinary Popular Delusions and the Madness of Crowds, The Man Who Mistook his Wife for a Hat
3. Books that highlight patterns in the world
   • Examples: Anti-intellectualism in American Life, Connections, Bowling Alone, On Bullshit, Metaphors We Live By, Better Angels of our Nature

Books that offer theory

1. Books with models of how a phenomenon works
   • Examples: Thinking Fast and Slow, How Animals Work, On the Origin of Species, Consciousness Explained
2. Books with models of what makes something succeed or fail
   • Examples: Zero to One, Film as Film, Democracy in America, Death and Life of Great American Cities, Seeing Like a State
3. Books that point out a problem
   • Examples: Bad Pharma, Breaking the News
4. Books that make predictions
   • Examples: Superintelligence, Age of Em, The End of History
5. Books that give you a general concept or lens you can use to analyze many different things
   • Examples: The Strategy of Conflict, Black Swan, A Pattern Language, Small Worlds, Clock of the Long Now

Books that change your values

1. Books that make an explicit argument about values
   • Examples: Against Democracy, Robot’s Rebellion, Genealogy of Morals, Doing Good Better, A Theory of Justice
2. Books that function as thought experiments for you to reflect on how you feel about something
   • Examples: Brave New World, Age of Em, An Inspector Calls
3. Books written from a holistic value structure, letting you experience that value structure from the inside
   • Examples: Atlas Shrugged, Walden, The Trial, Hitchhiker’s Guide to the Galaxy

Books that change your thinking style

1. Books that teach principles of thinking directly
   • Examples: How to Solve It, Language Truth and Logic, Philosophical Investigations, Intuition Pumps
2. Books from which you can learn a style of thinking by studying the author’s approach to the world, or to his material
   • Examples: Surely You’re Joking Mr. Feynman, Freakonomics, Godel Escher Bach
3. Books that tickle your aesthetic sense in a way that obliquely makes you a more interesting, generative thinker
   • Examples: Labyrinths, Invisible Cities, Arcadia, Aha! Insight