A rambling book by a glib and self indulgent author. It is laced with anecdotes and illustrative stories even while cautioning against the use of such devices. The central theme is that random and unforeseeable events (such as the "discovery" of black swans when all swans were thought to be white) have a great impact on our lives, and that most of what we see as progress is the result of these discontinuities, as opposed to the results of hard work. He calls for skepticism in all things.
I think he's looking at things the wrong way, and cherry picking to support his arguments. He also sounds like the kind of person I would get stuck listening to at a cocktail party. Clever, but without direction.
One primary theme throughout the book is that sudden change comes about suddenly and is of greater impact than the daily machinations of the average person. He gives several examples, the internet being one, as if it just sprang into being one fine day without decades of work being put into it by thousands of scientists and enginners. OK, so we can forgive his blindspot. When something arrives to his conciousness he might well think it just happened recently and miraculously without any forsight, and it might indeed have great impact on him. But that doesn't mean it "just happened". This is the kind of thinking leads one to believe in saltation of species as opposed to the slow and methodical processes that we know to be true.
Much of it seems wrong, being based upon reasoning by analogy. Much of the rest seems obvious, such as the admonishment not to cross the street while wearing a blindfold. A lot of it is pretty obviously made up, such as the story about Yevgenia Krasnova. In the end, there's very little you can take away from this book, except perhaps fodder for your own cocktail conversations.