This book is about using small failures to define the path to large successes.
It's OK to feel around in the dark with the only plan to move forward once the path becomes clear. This is not a passive strategy by any means; but it respects that you can't plot a straight course from where you are to where you want to be, and that this is acceptable.
"The best way to predict the future is to invent it." -- Alan Kay, technologist & inventor
I had an epiphany while reading it; I left a job of 18 years for many reasons, but this book crystallized for me one of them. For the first 15 years of my career, it was OK for me to look dumb: I could ask questions of anybody at any time -- I was dumb but trying to get smarter -- and such self-improvement was encouraged by the culture. Around 2007, this changed, probably due to the intense pressure the firm was under. If you looked dumb, maybe you were, so people stopped asking questions and started covering their a$$es. It seemed to me that folks there have stopped allowing themselves to make the necessary small errors. Too bad.
(A similar theme emerges in Rework
. Small companies make mistakes on purpose; in big companies, failures are not tolerated. Perhaps that's because in big companies the failures are bigger.)