The Black Swan by Nassim Nicholas Taleb

What it is about:

The Black Swan is two masterclasses condensed into one book. One in probability and statistics and another on how we humans are uniquely ill suited to handle and make sense of variability and rare events. On the surface, the book defines Black Swan events as very low probability events that nevertheless happen, giving multiple examples from the success of Google to the 9/11 tragedy. Digging deeper, it is about how long probability tails come back to bite us when we don't explicitly consider them. The book is also an indictment of simple minded "dashboards" and "risk mitigation" strategies that rely on "point estimators" like averages, medians and the like.

Why it changed my thinking:

Having been educated in Industrial engineering and operations, I learned the destructive effects of variability in the performance of systems and how the best optimized plans went south in a handbasket as soon as they were implemented. My early career in software and systems development only reinforced this (incorrect) perception of "can't control it, it may not be even worth trying". This book brought together for me a bunch of tools and concepts that were in my mental attic and put them to work to build more resilient systems, organizations and product portfolios.

Where to get it:

(Note, if you buy from the links here, I get a little commission back)