How Doctors Think
Jerome Groopman
Brynne will write far more comprehensibly about "How Doctor's Think" but to frame it a touch: I found this to be a sensational companion for contemplating practically all of the many pitfalls available at every moment in my own work. The fact that doctors were the point of reference only made the points more impactful in that everyone interacts and has certain conceptions of doctors that are powerful ones to pit against the "reality" that Groopman reveals.
Introduction to Logic
Irviing M. Copi
Building blocks for clear thinking which some of the time helps in investing :)
Judgement under uncertainty: Heuristics and biases
Edited by: Daniel Kahneman, Paul Slovic Amos Tvers
Dan Kahneman worked on behavioral psychology for 30+ years and then the mainstream recognized the huge hole his thinking could fill -- won the Nobel prize in economics
The World Greatest Blackjack Book
Lance Humble
One of my investment mentors encouraged me to start counting cards which I did for a few years... Never with high stakes in mind but it fueled my passion for portfolio management and understanding odds of all sorts.
Sway: The Irresistible Pull of Irrational Behavior
Ori Brafman and Rom Brafman
Good illustrations about traps leading to poor decision making
Think Twice: Harnessing the Power of Counterintuition
Michael J. Mauboussin
Mike is one of the sharpest thinkers out there that is able to provide a bridge between the financial markets and reality-based processes of decision making... The two topics need not necessarily live on entirely different islands. This book would be good as required reading in life frankly but at least as a counter force for anyone that winds up surviving thru all three rounds o the CFA.
Deep Survival: Who Lives, Who Dies, and Why
Laurence Gonzales
One of many reasonably good books about decision making. At his heart Laurence Gonzales is a superb pop story teller which, for me, distracts from the power of the learning... I am picky about my "entertainment" vs "substance" ratios in my intake and I think this went toward high drama examples of on the edge decision making.