My favorite book of 2020 was Navalmanack, by Naval Ravikant. Best of all, it’s free. Naval is a philosopher and entrepreneur, and this book collects his interviews, tweets and articles over the years. What you get is helpful mental models for navigating life. Navalmanack is the best book I’ve read in five years.
Off the Road, by Carolyn Cassady, wife of the legendary Beatnik Neal Cassady (Jack Kerouac’s best friend). If you’ve read Kerouac’s novels, you know about Neal Cassady’s wild adventures. Carolyn’s perspective on these “adventures” is quite different than Kerouac, however. She is honest and unsparing, though she doesn’t judge. As a man, this book was a revelation on the perspective of marriage from the other side. I learned a lot.
Christ Stopped at Eboli, Carlo Levi. Italian-Americans typically arrived from Southern Italy. They fled unbelievable poverty, feudalism and oppression. Levi was exiled to Southern Italy for his opposition to fascism, and he details the people and culture he encountered there. It’s an incredible book for anyone interested in Italian immigrants.