I'm now half-way through reading "Fooled by Randomness" by Nassim Nicholas Taleb. It was a great read and really drives home some of the concepts that have been lingering at the back of my mind regarding luck, complexity that really can't be simplified into MBA-happy charts/2-by-2 tables and the counterintuitive nature of probability. The author says it much better, so I'd just reiterate a few lines from the book that struck a chord for me:
"...Einstein's remark that commonsense is nothing more than a collection of misconceptions gathered by age eighteen."
"People in most fields...do not have problems eliminating extreme values from their sample...a professor who computes the average of his students' grades removes the highest and lowest observations, which we call outliers...a weather forecaster does the same with extreme weather...an event, though rare, that brings large consequences cannot just be ignored."
"The frequency or probability of the loss, in and by itself, is totally irrelevant; it needs to be judged in connection with the magnitude of the outcome."
"Quite impressive poetry has been produced...with the aid of a computer (via Monte Carlo engine)"