Winning the Lottery: What Would You Do?

I was talking with a friend recently about winning the lottery. It's a great fantasy to think about getting a ton of money and turning in your old life for a new one filled with buckets of caviar, gold plated computers and money fights.

When most people talk about winning the lottery, they think about what they would buy, and my friend was no exception.

“What would you do?” I asked him.

He immediately began rattling off a detailed list of purchases that he would make. It was clear this was not the first time he had thought about this.

I interrupted him, “But what would you do?"

He stopped and pondered in silence for a while. This was not something he had thought about.

As great as it would be to win enough money never to have to work again, waking up each day with no real sense of purpose isn't enough for me. I need to be doing something, though if I didn't have to do anything, I'm not sure what I'd do. Maybe I'd write full time. Or perhaps I'd find a cool hobby or take up golf. I'd like to see more of the world than just the United States.  But the reality is while all of these things sound like fun they aren't enough to fill up the rest of my life. I would need to be challenged. I would need to turn on my brain. Vacations are fun, but if there is nothing to counter-balance them, it's easy to imagine life becoming stale.  Without the need to work, what would propel me through life?  I'd like to think that I would be the type of person to use my financial freedom to better the world in some way--start a charity or something noble like that.  

The idea of filling up your life with possessions is easy, but filling up all of that time is much harder. If given all of that money and all of that freedom, what would you do with it?