'Going back to work' isn't necessarily something I see as admirable. It is what it is, but instinctively I've got more respect for people who make the most of their wealth in life experiences (and charity, natch).
If I hit a big jackpot, I might settle down and open up a gallery that made art available to the average person. But I'd spend a good chunk of time exploring first. I want months in Japan and New Zealand/Australia and a solid year in Europe, before we even get to driving across the US multiple times. I hear there's a coastal city in Chile that's pretty much the South American San Francisco, too...
Of course, I'm young(ish), single and have no kids. So I can wander through Europe without worrying about Timmy getting to school.