Masterpieces of Thought: 26 Philosophical Books That Remain Relevant

I was asked recently what works of philosophy made the biggest impression on me personally, and helped to shape my views on science, institutions, AI, tech, ethics, human flourishing, and life. Here is the list I came up with:

1. Deutsch's "Beginning of Infinity" - A 21st-century classic and the most discussed book in Silicon Valley. Dive into the infinite potential of human knowledge and progress; a world-class physicist lays out the philosophy of knowledge, science, engineering, and progress.

2. Dalio's "Principles" - Learn from Ray Dalio's approach to life and work, centered on radical transparency and meritocracy, embracing mistakes and learning from them, and defining clear principles and values. It pairs well with the philosophical parts of Isaacson’s biography of Elon Musk.

3. Koren's "Wabi-Sabi for Artists, Designers, Poets & Philosophers" - Embrace the beauty of imperfection and transience through the Japanese aesthetic of Wabi-Sabi (read Sen no Rikyu, Miyamoto Musashi, or Kevin Kelly’s “Excellent Advice” next).

4. Pinker’s “Enlightenment Now” - See why the world has progressed so much in the last 1000, 100, 50, and 20 years, why the news media is terrible with its negativity bias, and how to think about Enlightenment values now and in the future (the modern heirs are also Popper and Kuhn).

5. Nussbaum's "Fragility of Goodness" - Uncover the delicate balance between ethics, luck, and moral choices (follow up with Amartya Sen or Bernard Williams).

6. Munger’s “Poor Charlie's Almanack: The Wit and Wisdom of Charles T. Munger” - Get a brilliant polymath’s multiplexed ideas and frameworks. I haven’t enjoyed a book as much since Einstein’s “Ideas and Opinions.”

7. Friedman's "Free to Choose" - Explore the power of economic freedom and individual choice (best read with Von Mises, Schumpeter, and Hayek, then the Naval and Balaji readers).

8. Rand's "Fountainhead" - Understand the importance of individualism, creativity, and integrity as Roark strives to be a builder. Read Rand’s West Point essay “Philosophy: Who Needs It?” and then Karl Popper and Wittgenstein afterward (and Monk on Wittgenstein).

9. Rawls' "Theory of Justice" or "Political Liberalism" - Contemplate the principles of fairness and social justice in a pluralistic world where common values and culture may not intersect much. Read the Pogge biography of Rawls.

10. Frankl's "Man's Search for Meaning" - Walk in his shoes and learn the insights of a Holocaust survivor who found meaning and purpose amidst hellish suffering. Zoom out to Shirer’s “The Rise and Fall of the Third Reich” to get more context.

11. Hesse's "Siddhartha" - Watch the spiritual journey of a person who tries to develop self-knowledge and inner peace tin Siddhartha, including thinking, waiting, and fasting. Follow up with Easwaran’s “The Dhammapada”, Rahula’s “What the Buddha Taught,” or the Karen Armstrong biography.

12. Tolstoy's "War and Peace" - Delve into the complexities of human nature, love, and morality set against the backdrop of the Napoleonic Wars in Russia. Follow it up with Proust if you want to mess your life up.

13. Mill's "On Liberty and Essays" - Reflect on the significance of individual freedom and self-expression, and why they are crucial to a functioning society and republic. Strangely I think Mill pairs well with “Conversations with Jean-Paul Sartre.”

14. Darwin's "Origin of Species" - Read the original text with revolutionary ideas that shaped our understanding of evolution, and now the memes and forces shaping human society and AI. His other books are worth it too, including his “Autobiography” and “The Expression of the Emotions in Man and Animals.”

15. Benjamin Franklin's "Autobiography" - Delve into the life and wisdom of one of America's (and arguably the world’s) most influential figures, learning the pragmatic philosophy behind his curiosity, inventiveness, and pursuit of self-improvement. The Brands and Isaacson biographies of Franklin are wonderful too.

16. Smith’s “The Wealth of Nations” and “Theory of Moral Sentiments” - Read two of the most important Enlightenment books; they need to be read together. You can also add a Voltaire reader, selections from Locke/Montesquieu/Rousseau, and key pieces by Newton and Leibniz (eg. Principia and Monadology).

17. Kant's "Metaphysics of Morals" - Grasp the foundations of moral philosophy and ethical reasoning; this is Kant-lite and quite readable. More Kant comes in Want’s “Introducing Kant: A Graphic Guide” (the comic book is better than the original prose).

18. “Patanjali Yoga Sutra” (Bryant translation) - Explore the transformative eight-fold path of yoga and self-understanding in one of the earliest texts of applied psychology. Mallinson’s “Roots of Yoga” comes next.

19. “Bhagavad Gita” (Barbara Stoller-Miller or Easwaran translation) - Dwell on the timeless wisdom of Indian spirituality and philosophy. To go deeper, read Easwaran’s translation of the Upanishads or Davis’s biography of the Gita.

20. Confucius' "Analects" (Ames translation) - Delve into the principles of virtue, ethics, and social harmony, to understand Ren, Li, Xiao, Yi, and Zhi (weakly translated as humaneness, propriety, family respect, righteousness, wisdom). Read Laozi’s Tao Te Ching next.

21. "Chapters of the Sages / Pirkei Avot" (Bulka translation) - Gain insights from Jewish Talmudic wisdom and ethical teachings, like this one: “If I am not for me, who will be for me? And when I am for myself alone, what am I? And if not now, then when?”

22. Seneca's "Letters from a Stoic" (Penguin edition) - Absorb the teachings of Stoic philosophy for an integrated life, from a man who helped run the Roman Empire (and was superior to Marcus Aurelius).

23. Epictetus' "Handbook" (Oxford translation) - Master the art of resilience and inner strength through Stoicism, from a slave who was a master more than most consuls or emperors.

24. Sophocles' "Antigone" (Fagles translation) - Delve into themes of loyalty, morality, personal ethics, and the individual's struggle against authority in this poignant and thought-provoking play.

25. Aristotle’s “Nichomachean Ethics”, “Politics”, “Rhetoric”, and “Poetics” (McKeon Modern Library edition or Terence Irwin). The OG student of Plato and perhaps his opposite - see why his ghost still haunts all modern philosophy and much science.

26. Plato's "Complete Works" (Cooper translation) - Engage with the biting, painful, and sharp dialogues that shaped Western philosophy, especially Phaedo, Phaedrus, Meno, Symposium, Theaetetus, Parmenides, Protagoras, the Apology, and the flawed but magnificent Republic.