It took me a really long time to finally read this 2007 book (not related at all to the current Natalie Portman movie of the same name).
The whole point of this book is to make a long, winded argument about why the impact and occurrence of the highly improbably is consistently underestimated, with huge consequences for everybody. While it is a rambling, philosophical book whose point could have been put much more succinctly in half the amount of paper, it is also a very interesting (and some would say prophetical) way of looking at the world as one can see from the interview below.