This is a more complete list of books than the top picks list. The books are roughly in the order in which I’ve read them, though I’ve reread some several times and a few incompletely. I only lightly curated entries after about 2012 while being more selective with inclusion of earlier books.

I tend to have a high bar for reading books. I stick with blogs, articles, and Wikipedia when possible. Given the prevalence and quality of such information sources, a list of books isn’t as representative a window into my mindset as it once would have been. But it is still a window, highlighting the concepts I found important enough to dive into for understanding, motivation, or exploration.

• Duncan K. Foley, Understanding Capital: Marx’s Economic Theory
• Plato, Plato: Five Dialogues: Euthyphro, Apology, Crito, Meno, Phaedo
• Plato, Republic
• John S. Dryzek, The Politics of the Earth: Environmental Discourses
• John McPhee, Encounters with the Archdruid
• John Stewart Mill, Autobiography
• Friedrich Wilhelm Nietzsche, On the Genealogy of Morality
• Peter Lynch, One Up On Wall Street
• Louis P. Pojman, Ethical Theory: Classical and Contemporary Readings
• Richard Dawkins, Unweaving the Rainbow: Science, Delusion and the Appetite for Wonder
• Robert T. Kiyosaki, Rich Dad Poor Dad: What the Rich Teach Their Kids About Money That the Poor and Middle Class Do Not!
• Neal Stephenson, Cryptonomicon
• John Stuart Mill, Utilitarianism
• Robert M. Pirsig, Zen and the Art of Motorcycle Maintenance: An Inquiry into Values
• John Stuart Mill, On Liberty
• Charles Murray, Bell Curve: Intelligence and Class Structure in American Life
• Malcolm Gladwell, Blink: The Power of Thinking Without Thinking
• Neil Postman, Technopoly: The Surrender of Culture to Technology
• Katharine Tait, My Father, Bertrand Russell
• Bertrand Russell, Autobiography
• Paul Graham, Hackers & Painters: Big Ideas from the Computer Age
• Isaiah Berlin, The Hedgehog and the Fox: An Essay on Tolstoy’s View of History
• Steven D. Levitt, Freakonomics: A Rogue Economist Explores the Hidden Side of Everything
• Irving Kristol, Neo-conservatism: The Autobiography of an Idea
• Leo Tolstoy, Anna Karenina
• John Rawls, Justice as Fairness: A Restatement
• Robert Greene, The 48 Laws of Power
• David JC MacKay, Sustainable Energy – Without the Hot Air
• Nassim Nicholas Taleb, The Black Swan: Second Edition: The Impact of the Highly Improbable
• Venkatesh Rao, The Gervais Principle: The Complete Series
• Venkatesh Rao, Tempo: timing, tactics and strategy in narrative-driven decision-making

2012

• T.J. Stiles, The First Tycoon: The Epic Life of Cornelius Vanderbilt
• Garry Kasparov, How Life Imitates Chess: Making the Right Moves, from the Board to the Boardroom
• Judith Martin, Miss Manners’ Guide to Excruciatingly Correct Behavior
• Dale Carnegie, How to Win Friends & Influence People
• Isabel Briggs Myers, Gifts Differing: Understanding Personality Type
• G.K. Chesterton, Orthodoxy
• Nassim Nicholas Taleb, Antifragile: Things That Gain from Disorder

2013

• Larry E. Swedroe, The Only Guide You’ll Ever Need for the Right Financial Plan
• Harry Browne, Why the Best-Laid Investment Plans Usually Go Wrong: And How You Can Find Safety and Profit in an Uncertain World
• Michael Lind, Land of Promise: An Economic History of the United States
• John Gray, Straw Dogs: Thoughts on Humans and Other Animals
• James C. Scott, Seeing like a State: How Certain Schemes to Improve the Human Condition Have Failed
• Amy Chua, Battle Hymn of the Tiger Mother
• Alain De Botton, The Pleasures and Sorrows of Work
• Samuel C. Florman, The Existential Pleasures of Engineering
• Francis Fukuyama, The End of History and the Last Man
• Francis Fukuyama, The Origins of Political Order: From Prehuman Times to the French Revolution
• Larry E. Swedroe, The Only Guide to a Winning Investment Strategy You’ll Ever Need
• Alain De Botton, Religion for Atheists: A Non-believer’s Guide to the Uses of Religion
• Alain De Botton, The Consolations of Philosophy

2014

• Alasdair MacIntyre, After Virtue: A Study in Moral Theory
• Michael Lewis, The Big Short: Inside the Doomsday Machine
• Jane Jacobs, Systems of Survival: A Dialogue on the Moral Foundations of Commerce and Politics
• Daniel Kahneman, Thinking, Fast and Slow
• Robert M. Pirsig, Lila: An Inquiry Into Morals
• Thomas Sowell, A Conflict of Visions: Ideological Origins of Political Struggles

2015

• Francis Fukuyama, Political Order and Political Decay: From the Industrial Revolution to the Globalization of Democracy
• Burton G. Malkiel, A Random Walk Down Wall Street: The Time-Tested Strategy for Successful Investing
• Bruce Bueno de Mesquita, The Dictator’s Handbook: Why Bad Behavior is Almost Always Good Politics
• Irving Kristol, The Neoconservative Persuasion: Selected Essays, 1942-2009
• Francis Fukuyama, Our Posthuman Future: Consequences of the Biotechnology Revolution
• Francis Fukuyama, America at the Crossroads: Democracy, Power, and the Neoconservative Legacy
• Jonathan Haidt, The Righteous Mind: Why Good People Are Divided by Politics and Religion
• Karl Polanyi, The Great Transformation: The Political and Economic Origins of Our Time
• Alasdair MacIntyre, Dependent Rational Animals: Why Human Beings Need the Virtues
• Francis Fukuyama, Trust: The Social Virtues and The Creation of Prosperity

2016

• Jean-Jacques Rousseau, Emile: Or On Education
• George Steiner, Nostalgia for the Absolute
• William Zinsser, On Writing Well: The Classic Guide to Writing Nonfiction
• Ashlee Vance, Elon Musk: Tesla, SpaceX, and the Quest for a Fantastic Future
• Eric Hoffer, The True Believer: Thoughts on the Nature of Mass Movements
• Neal Stephenson, Seveneves
• Andy Weir, The Martian
• Steven Pinker, How the Mind Works
• Nassim Nicholas Taleb, Fooled by Randomness: The Hidden Role of Chance in Life and in the Markets
• Gordon Neufeld, Hold On to Your Kids: Why Parents Need to Matter More Than Peers
• Neal Stephenson, The Diamond Age: Or, a Young Lady’s Illustrated Primer
• Deirdre N. McCloskey, Bourgeois Equality: How Ideas, Not Capital or Institutions, Enriched the World
• Henry Kissinger, World Order
• Ted Chiang, Stories of Your Life and Others

2017

• Albert O. Hirschman, Exit, Voice, and Loyalty: Responses to Decline in Firms, Organizations, and States
• Matthew B. Crawford, Shop Class as Soulcraft: An Inquiry into the Value of Work
• William Strauss, The Fourth Turning: An American Prophecy – What the Cycles of History Tell Us About America’s Next Rendezvous with Destiny
• Norbert Wiener, Ex-Prodigy: My Childhood and Youth

2018

• John Holt, Teach Your Own: The John Holt Book Of Homeschooling
• Amy Chua, The Triple Package: How Three Unlikely Traits Explain the Rise and Fall of Cultural Groups in America
• J. D. Vance, Hillbilly Elegy: A Memoir of a Family and Culture in Crisis
• Pieter Hintjens, The Psychopath Code: Cracking the Predators that Stalk Us
• Fred Waitzkin, Searching for Bobby Fischer: The Father of a Prodigy Observes the World of Chess
• Steven Pinker, The Blank Slate: The Modern Denial of Human Nature

2019

• Iain King, How to Make Good Decisions and Be Right All the Time: Solving the Riddle of Right and Wrong
• Susan Daniels & Michael M. Piechowski, Living With Intensity: Understanding the Sensitivity, Excitability, and the Emotional Development of Gifted Children, Adolescents, and Adults
• Greg Lukianoff & Jonathan Haidt, The Coddling of the American Mind: How Good Intentions and Bad Ideas Are Setting Up a Generation for Failure
• Marylou Kelly Streznewski, Gifted Grownups: The Mixed Blessings of Extraordinary Potential
• Laszlo Polgar, Raise a Genius!
• Ann Hulbert, Off the Charts: The Hidden Lives and Lessons of American Child Prodigies
• Josh Waitzkin, The Art of Learning: An Inner Journey to Optimal Performance
• Howard Fast, Spartacus
• C. S. Lewis, The Abolition of Man

2021

• Robert Kegan, In Over Our Heads: The Mental Demands of Modern Life
• Paul Bloom, Against Empathy: The Case for Rational Compassion
• Johann Wolfgang von Goethe, Wilhelm Meister’s Apprenticeship