Philosophy
Meditations
A two-thousand-year-old reminder that the work of being a steady human is mostly internal, and mostly about returning to the present. I re-read passages of this every winter.
Bookshelf
Books worth re-reading.
There are thousands of books. There are perhaps fifty that have actually changed how I live. Here are six of them. The rule for getting on this shelf is simple: I have read it more than once, and the second reading was better than the first.
Philosophy
The Bhagavad Gita
Do the work; release the outcome. Said cleanly, repeatedly, in language that survives translation. The single most useful book on equanimity I have read.
Finance
The Psychology of Money
The first book I recommend to anyone starting their personal-finance journey. It is not about money, really. It is about the very strange relationship between humans and the future.
Leadership
Radical Candor
Care personally, challenge directly. Two phrases you can carry into every 1-on-1 you ever run. The book around them is structured advice on how to actually do it.
Systems
Thinking, Fast and Slow
An owner's manual for your own mind. Once you have read it, you cannot unsee the cognitive biases that drive most bad decisions — your own and other people's.
Self
The Second Mountain
The first mountain is career, achievement, status. The second mountain is meaning, contribution, and the people you build a life with. Most of us are on the first mountain too long.
Finance
Rich Dad, Poor Dad
Not everything in this book is correct, and that is fine. What it gives you is a frame — that there is a real difference between earning money and building wealth, and that the second is a learnable skill, not an inheritance. I hand it to almost every young professional starting on personal finance.