Rachael over at Yarn-A-Go-Go asked today what we’d do if we won the lottery. You know, after paying everything off and investing and perhaps making sure your family members have homes of their own. What would you do then?

We had an assignment like this in sixth grade. “What would you do with a million dollars?” I don’t remember Mr. Isenberg’s intent, although I remember worrying about it at the time. Was he trying to see who the better people were at the ripe old age of 11ish? Should I just say I’d give it all away to cure cancer or give orphans homes or something?

Funny, now, to realize what a tiny drop in the bucket my imaginary million would’ve been. One measly fucking million to cure cancer? Would that it were that cheap and easy.

Thing is, I didn’t have any context for the stuff I could buy with it, either. I didn’t have any idea what things cost. I think I said I’d get a house and a Ferrari or some other random luxury car that the boys in my class always talked about. And I’d buy houses for some other people, too! Then I’d give the rest away…although I didn’t know where, and I only said it because I had bupkiss for ideas. I remember looking through magazines trying to find something I’d want to buy, but that didn’t even help because there were never any prices in the ads (this, of course, was pre-Google). I could buy all the Sweet Valley High books EVER, but they were maybe $7-10 each. You know how long it takes to get to a million at $7 each?

I never trusted or liked Mr. Isenberg. I didn’t learn much that year, either. Two points to whoever can pin a meaning on that stupid assignment.

Anyway, I haven’t thought about it in years, and I’m kind of glad Rachael made me think about winning the lottery. I don’t play the lottery and I haven’t scratched a scratch-off since…my ex-MIL put them in my Christmas stocking. But thinking about what I would do with the cash isn’t a bad way to dream up my ideal lifestyle in a way for which I never seem to have time. Or? I’m so focused on the present that “ideal” seems like a waste of brainpower…because “really, really good” turns out to be quite enough.

Here’s my list, after, of course, paying things off, investing wisely, and Helping People (college tuition, family gifts/trusts, that sort of thing):

• One house with all the amenities (and connectivity) we need, plus fully serviced condos in the places we visit (or expect/wish to visit) often
• Expansive, proper wine storage solution and membership in a longish list of wine clubs
• Unlimited car service
• Three to four weeks exploring somewhere different every year. Europe, Australia, Iceland…
• Two weeks every year wherever we find most relaxing (haven’t found it yet, but am on the watch…)
• A personal shopper — I don’t like clothes shopping and would be happy to let someone else develop my personal style.
• POOL! Also, pool maintenance.

Seriously, that’s kind of all I came up with. It’s a short list. It’s not entirely out of reach. That’s sort of…eye-opening, I think.

What would you do with your winnings?