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Zen & The Art of Motorcycle Maintenance This helped me understand the duality of the logical/mechanical and the creative/artistic. Then merging the two.
Another was Nineteen Eighty Four by Orwell.
I'd also cite The Fountainhead by Ayn Rand as having influenced me, although I read it when I was older and found that it mostly reinforced ideas that I was already sympathetic towards. Similar situation with Atlas Shrugged, also by Rand.
I could probably also call out The Soul of a New Machine by Kidder, as being a primary influence that pushed me in the direction of getting involved with computers.
Atlas Shrugged
Reading Rand’s essays both made me appreciate her views more and made me cautious to accept her epistemology as a whole. I don’t consider myself an Objectivist, but I still consider her work to be a strong influence on my life.
"Difficult Conversations: How to discuss what matters most". I bought this on the strength of an HN suggestion. It's like Design Patterns for human conversations: the result of studying how people interact, common patterns that work, and how things break down. Really crystallised a lot of insights I'd perceived but never thought about systematically. I highly recommend it. Word of warning - there are a few books with…
Measure what Matters by John Doerr had a similar effect on me to what you're describing with Freakonomics. I don't remember a lot of details from that book, but the way I set and measured goals after reading it changed almost overnight.
It changed the way I see the world, how to have a sceptical mind and not only how but why one should question.
And also, it shows to me that, if you don't have a answer for something, doesn't mean that it can not be true. It's just that you don't know. And for a lot of things, this is the correct and only answer that we can have now.
Bottom line: judge your success in life by how well you make your decisions, not by your outcome. You have full control of your decisions, and often no control at all over their results.
Man’s Search for Meaning by Viktor E. Frankl
A Guide to the Good Life: The Ancient Art of Stoic Joy by William B. Irvine
The Selfish Gene by Dawkins. The gene is the unit of replication, and this affects every process in this universe.