not realizing earlier that discomfort is closely correlated with learning
pride
too much self reliance
inaction
discomfort with not knowing everything
Anna Karenina by Leo Tolstoy
Just Kids by Patti Smith
Norwegian Wood by Haruki Murakami
Hitchhiker's Guide to the Galaxy by Douglas Adams
Someone Who Will Love You in All Your Damaged Glory by Raphael Bob-Waksberg
Winners Take All by Anand Gridharadas
Sculpting in Time by Andrei Tarkovsky
Born Standing Up by Steve Martin
The Autobiography of Malcolm X by Malcolm X
The Rise of Theodore Roosevelt by Edmund Morris
Man's Search for Meaning by Viktor Frankl
The Unbearable Lightness of Being by Milan Kundera
Excellent Sheep by William Deresiewicz
Patrimony by Philip Roth
Climate change + energy (including water, food, natural disasters, global warming, secure and sustainable energy sources)
Education (including K12 quality, higher ed cost, adult re-education)
Inequality (including racism, immigration, diversity)
Centralization of data and power in opaque or dysfunctional systems (including security)
Media's uncertain future (as a tool for democracy)
Future of work (aging population, automation)
Healthcare (cost, quality, drug development, consumer model)
Personal finance (in an increasingly insecure world)
Housing (cost) and transportation
Food security (nutrition + cost)
Artificial intelligence
Synthetic biology