I read and really enjoyed Michael Mechanic's Jackpot: How the Super-Rich Really Live last year, and one thing about lottery winners and the sudden tech millionaire crowd is that sudden wealth was effectively a system shock for them. There's a lawyer who specializes entirely in helping new lottery millionaires navigate the issues ranging from lost cousins coming out the woodwork to where to put their money. Worth a read for that section alone.

While I would love to have more wealth (or maybe less worries about lack thereof), I think I'm pretty okay with the idea of not being suddenly thrust into oodles of it, much as I might have delighted in that when I was younger.