The Black Swan
Nassim Nicholas Taleb is one of my favortie authors, even though I've only read two of his books: Fooled by Randomness and The Black Swan. Both offer challenges to anyone making predictions about the future (stock market behavior, corporate success or failure, community acceptance of a technology, which restaurant in town will survive for 2 years, etc.). Oddly enough, my financial advisor recommend I read Fooled by Randomness. At the time, I was toying with the idea of using a set of "predictive" stock price functions to help me pick winning stocks. After reading Fooled By Randomness I realized that I did not have the temperment, bravado, or intellect to outwit the NYSE, NASDAQ, and most of all, the impact of randomness. Furthermore, it reinforced that I don't know everyting that I don't know.
I doubt that I will do Taleb's premise justice, but the general idea is this:
Euproean explorers assumed that all swans were white because all of the swans they had seen were white. After exploration of Australia, they found a black swan. Black swans, though rare, smash the previously common belief that swans come in only one color. The discovery of the black swan was nearly impossible to predict. The black swan metaphor extends to how we view the future. According to Taleb, it is in our nature to assume the future will follow the pattern of the past. When black swans appear, they send shockwaves and often radically change the course of history (consider 9/11, WWI and WWII, the internet, lasers, Long Term Capital Management, etc.)
The takeway here is that we cannot know the future, yet we often lull ouselves into a sense of certainty about it. As evidence, consider all the books in the bookstore that describe how to become a Millionaire in 10 easy steps or how to pick stocks like the pros. Randomness has more to do with our own existence, success, or failure than we often care to consider. It is not that we should not take risks, but rather, we should be aware of the full spectrum of risks we are taking. All too often we wrongly assume that risks fit in a tidy box.
I haven't fully processed the ideas Taleb offers in these books, but I am certainly going to think twice before postulating with certainty about the future of the world of web services...