A free society is as much a threat to the intellectual's sense of worth as an automated economy is to the workingman's sense of worth. Any social order that can function with a minimum of leadership will be anathema to the intellectual.
Biggest lesson? Discovering that the less I think about myself and the more I think about what I can do for others, the more I get out of life. Ultimately, it makes me a happier person. You have to give it away if you want to get it back. After all, humility isn't thinking less of yourself, it's thinking of yourself less.