At the end of the year, all unspent money goes poof, even if it's money that didn't exist at the beginning of the year (like, interest earned, etc.)

I suspect my answers will not be unusual.

-Pay off all my debts at once, and breathe freely.
-Take an unpaid leave of absence from work for a month and go traveling with my mom.
-Buy a house around Somerville, and buy houses outright for any of my closest who want that. Go crazy with efficiency (solar panels, that sort of thing).
-Buy my mom an apartment someplace she likes around Boston.
-Set aside enough money to not have to work for a year when I have a child. Oh wait, that doesn't fit your requirements. Buy a bunch of stuff that I'll need when I have a kid? I feel that that'll happen soon enough for me to plan for it now. But maybe that's breaking the rules.
-Give money to cancer research, abortion services for women who don't have sufficient access to them, dementia research.
-Give money to my professional organizations.
-Go completely, totally crazy with bike gear, making sure I have enough diverse stuff to bike-commute year-round. Do the same for any of my friends who want it.
-Gift some select people with debt reduction or elimination, if they wish it.

Now I'm all a-fantasy. :) Surely there'll be more.

Also, I'd pay for whatever learning is deemed cool and wanted, for [some of] the kids in my vicinity. Schooling includes circus arts, travel and equipment (musical instruments?). Equipment would be shared if it lends itself to that.

1) Pay off and upgrade everything (house, car, clothes, full wardrobe for kids for upcoming 2 years)
2) Do #1 for my mom and sis.
3) Hire bestest project manager to fix cohousing headaches
4) Pay for making all cohousing headaches go away
5) TRAVEL for almost the whole year. Some with partner, some with kids, some with friends.
6) Buy a vacation home (sorry, I disagree that this doesn't count!)
7) Give 20% to some good cause/foundation/charity.

4) Pay for making all cohousing headaches go away
That trick does not actually work.

I'd buy a house, and then I'd probably start making grants. Is that within the bounds of the rules? If the grantees have to show that they've achieved what they said they would, or return the money, within the year? Of course, a year might not be enough time to properly set up a grant-giving (and evaluating) scheme...

Oh, right, and travel! I'd finally do my Kathmandu to Everest Base Camp trek, and take MRF to Italy for two weeks, and maybe go to Bali or Thailand or Vietnam or Australia. And maybe pay off my parents' house and buy one for my sister, too. But honestly, I didn't think about those things till I read other people's comments.

Edited at 2009-07-13 04:02 pm (UTC)

Among many other things, I'd keep a bunch of $20s in my pocket for giving away to panhandlers, even if I think they're not for real. 'Cause that would just make me happy.

After I was done with the boring stuff (pay off my house, pay off my debt, pay off my mother's house and debt), I'd buy my wife a couple of motorcycles and do some upgrades/renovations on the house.

Whatever was left over I'd use to produce lots and lots of the sort of experimental theater that has no hope in hell of paying for itself in ticket sales. I'd probably start with an all out production of Black Watch over at the warehouse space in Fort Point.

I'd top off the retirement accounts for my family, then donate the rest to the Jimmy Fund.

Ok maybe just one hooker and 8 ball, but the rest goes to charity.

What is this? I did all kinds of nice things for you with my imaginary millions!

1. Buy/build/modify my dream house with all H's and my crazy requirements.
2. Get a massage once a week or more as necessary so that I don't have a headache constantly.
3. I would also like to buy and furnish a house in Davis Square. I don't think it should count as a vacation home or second home because ideally I'd keep it empty for the 4-8 weeks a year that I'd be inhabiting it. And H would probably be in it even more.
4. Travel to the 3 continents I haven't been to yet.
5. Donate money to charities I care about.
6. Fund some research trips to Nicaragua so that I could collect my own data.
7. Donate money to some of the homesigner's families and for deaf-related research.
8. Pay absurd prices for front row tickets for some concerts.
9. Fly first class with H somewhere just because we can. I would probably buy him whatever car he wanted too.
10. And more...

Really, I could do it in a month! But this list might total more than 20 million... :)

Buy out all of the Mosaic and Camelot and Sawyer Hill units (well, i can't buy the 40b ones, but i can pay the bank for them) and our investors. Hopefully I can sell SOME of that within the year.

Pay off my house and my mom and my brothers houses and buy out my Dad from the house in maine, then build a new house up there.

New hybrid cars all around.

A new ski boat.

Buy Dave a big sailboat and a cottage on a mountaintop.

Can I pay the college fund? Can I prepay tuition at SVS and Simon's Rock?

A masseuse on staff for a year. and a Chiropractor. And all the dance shows I want to see, with a chauffeur.

Buy Simon's Rock whatever building is next on the wish list

And then there's the charities..

Edited at 2009-07-13 04:31 pm (UTC)

Prepaying counts as investing. Part of the spirit of the question is to get at how you would spend money if you couldn't use it for cushioning future economic hurdles.

buy a former factory, school, or other large building with tall ceilings and convert into into live/work space that the circus and band can use. make it fully accessible and as energy efficient as possible.

i'm sure the 20mil would juuust dent the surface of that, but with that kind of funding we could probably finance the rest or convince someone else to back it.

Multi-city "Safer Sex Festival Tour 2010" with celebrity headline acts.
Co-sponsored by Red Bull, Durex, Crisco, and Cirque du Soleil.

Oh the toys I would buy! :) I would create my dream lab and outfit it with all of the fun science equipment that I'd need to do whatever research strikes my fancy or the fancy of my friends! This lab would preferably be in my backyard (or maybe even on my own private island), so that I could just stumble in whenever I wanted, do whatever research I wanted, and then spend the rest of the day hanging out in the cozy house, hiking, or relaxing on the beach. This plan might be more ambitious than $20 million though :(

A couple of old Ferraris, a new minivan, prepaid prep school and/or college tuition for the kids, some Mosaic units, a house with a dock on Fishers Island's West Harbor, a couple of boats, lots of travel with and without the kids, and I'd give away a whole bunch in creative ways.

- Pay off all my & Ted's debt
- Pay off all my siblings' debt
- Make all the little fixes that need to happen at my mom's house happen, perhaps including building her the deck she's always wanted
- Buy mom the mustang convertible she's always wanted
- Buy a very nice house for Ted and I (not too nice, we want to be able to afford property taxes once we're no longer multi-millionaires)
- Travel a whole crapload
- Rent a yacht, travel in it a whole crapload
- Fly my closest friends to an amazing local, party for a week
- Repeat, this time with family
- Allocate a large portion to charity, perhaps including one that I can go and volunteer with somewhere else in the world

ooh, a few more...

- Pay a year of tuition (since it has to pay out within a year, right?) for my brother Joe, and any other siblings wanting to further their education.

- Hire a personal chef for my mom to cook her healthy, delicious, diabetic friendly meals.

- Give a bunch to fund after school enrichment activities for underprivileged kids in Oakland, as well as scholarships for Oakland kids who can't afford, but want, post-high school education.