Antifragile by NN Taleb -
Taleb is a philosopher / math guy. Famous for writing Black Swan. Antifragile is focused on life processes that get better with volatility. He is totally irreverent. He would piss you off if he wasn’t so damn correct!
Misbehavior of Markets by Benoit Mandelbrot.
In a hundred years, Mandelbrot will likely be considered one of the greatest mathematicians that ever lived. He invented fractal mathematics, basically the math of nature (as opposed to Euclidean math, the math of humans ;) ). This is NOT a math book but will greatly improve your ability to think about volatility and risk in markets (any market)
Lessons from Critical Thinkers by Albert Rutherford
A nice romp through the history of critical thinking. Will challenge you to think about how you think. Fast read. I read it twice
Love our shared interest in the Book of Joy. That was such a great book.
Also, given our interest in Book of Joy, you may like Why Buddhism is True by Robert Wright. I read this about 2 years ago
Another book that comes to mind is Factfulness by Hans Rosling. This book is pure Joy, written by a medical doctor and world health leader just before he died.