Today in the Friday Five, we’re getting hypothetical.

This topic is actually pretty near and dear to my heart right now, because there’s a $30 million lottery being held today, and I’d very much like to have a piece of it. Does it matter that it’ll probably end up going to a cigarette smuggler living in rural Quebec, who’ll use it to buy a new motorboat and bribe border officials? No, because I have hope. I have private little fantasies that occupy my mind while I’m in the shower in the mornings, trying to build up the momentum to put on my pants, to put the keys in the car, to work the entire day.

Lotteries are fun that way. They give you just a tiny little thing to look forward to, a tiny little hope that you might get lucky and everything in your whole life will change. You can’t be sure it’ll get better necessarily, but it certainly will change.


Be sure to check out Gwen’s Friday Five, since she has joined me in my quest to crawl up the ass of the Friday Five and kick its ass’ ass!

You know, I used to work with a guy who once told me– oh wait, hang on, we’re getting a bulliten here:

You have just won one million dollars.

Holy crap! And this isn’t even a spam e-mail that starts out by saying I’ve won a million dollars, if I’m willing to expand my definition of “won” to “became very interested” and my definition of “a million dollars” to “herbal penis enlargement pills that are 9 times more effective than Viagra.” This is the real deal!

1. Who do you call first?

The lottery commission! Ha ha ha ha! Because, see, if I won the lottery, then obviously I would want to claim my prize money, and you can’t really claim very much prize money if you call your mother and tell her you’ve got a winning ticket now can you, so obviously the first person you’d call is the gaming corporation to lay your claim to the prize, ohhh…

…ohhh, we have a good time, don’t we? Literal jokes are the best fun.

Who would my first phone call actually go to? Probably Sham, because she’s the only person I can think of who’d be more excited than I would at winning a huge big pile of money, and she’d have the same reaction that I would: complete and total disorientation. Of course, mine would stun me for hours and days, where hers would last about as long as it would take to say, “So when are you quitting your job?”

After that, I’d call my mother and give her the good news, first of all because she’d be almost as excited as Sham and I, and second because it would eliminate the need for me to phone anyone else. Once I relay the information to my Mom, I can more or less assume that the rest of my family — and by family, of course, I mean “all citizens of the free, Western world” — will hear about it in short order. It took two days for every blood relation of mine to know that I’d developed a hemorrhoid, so if I compare the relative hilarity of that situation to the enormity of a lottery win, I think my entire extended family would get the news in less than twenty-three minutes.

2. What is the first thing you buy for yourself?

A house, man. A great big house. One of those ridiculously gorgeous houses in the city, like the ones Meg Ryan is always living in when she does a Nora Ephron movie. Except instead of being a book editor or a small business owner or someone else who very obviously can’t afford it, I will instead be a lottery winner who can very much afford it, and quite possibly several cottages in the country.

Forget sports cars, forget jewels, forget spiffy clothes or some retarded keepsake connected to my childhood. I’m not the sort of person who’s going to rush out with his lottery cheque and buy that autographed picture of Dirk Benedict as Face Man from the A-Team that I never had as a child. I’m the sort of person who has been looking very seriously at how much money a God damned mortgage is going to suck out of his life for the next thirty years, and I am extremely keen to avoid that.

Then I would call the bank and leave a message for the manager, saying, “Hi, thank you for the letters you sent me in which you pre-approved me for a seventy-eight year mortgage at 135% interest, but I am afraid I will have to decline, and oh look at that, I just bought and sold you three times while I was leaving this message. Have a great — oops, just bought and sold you again — day!”

3. What is the first thing you buy for someone else?

Two plane tickets and a hotel reservation for those resorts in Bora Bora, where you live out in a hut and your glass-top coffee table can be rolled back so that you can reach in and touch the ocean. Because I promised that I would.

4. Do you give any away? If yes, to whom?

If it’s one million dollars, yeah I would, but I’d start getting nervous about it. If it was thirty million dollars, then absolutely I would, with no hesitation.

I suppose there’s really no difference between the two, except for the fact that I was born in a time when someone winning a million dollars was as astonishing as them sprouting wings and flying, and I now live in a time when the houses in my neighborhood cost roughly half that amount. So if I wanted to be a great benefactor of the masses — or even of my own family — I’d end up like Liam Neeson at the end of Schindler’s List, looking all around me and saying, “Not enough, not enough! These DVDs! That’s one of my sister’s mortgage payments! This home theatre! This is my uncle’s car insurance!”

I read recently that a very high percentage of lottery winners manage to run through their entire prize within two years of winning it, and a surprising number of them actually end up in worse financial shape than they were before they won. Much of this must certainly come from people exploding from the woodwork and trying to get a piece, but some of it must result from the natural sense of obligation that would come from a windfall like that. After all, if you can’t show generosity to the people around you, particularly your friends and family, then what kind of person are you? It’s one thing if it’s money you’ve earned, but if it’s cash that you’ve won? Easy come, easy go, you greedy fuck!

I once had a conversation with my father about this, and whether or not he’d give me any money if he won the lottery.

“Sure I would,” he said. “But it’s not like I could just carve a big piece out and hand it to you. It doesn’t work that way.”

“Right,” I said. “You get sort of an annuity from the gaming corporation, spread out over something like twenty-five years, don’t you?”

“Exactly. So that being the case, I’d make sure that we had our debts paid down, took care of the family, and then look into putting you on a stipend.”

“Like, an allowance? Wouldn’t that kind of make me beholden to you a little, Dad?”

“Well,” he said, “it is my money.”

Which I think sums things up rather nicely.

5. Do you invest any? If so, how?

Yep, in a big, low-to-medium risk mutual fund or something that will absolutely guarantee that when I get to retirement, I will not have to work as a fucking Wal-Mart greeter or something to make ends meet.

That isn’t to say that I wouldn’t want to spend a little and live while I was young. Just the opposite — I’d like to spend as much as possible living happily in a world full of sunshine and warmth while I’m young, traveling the length and breadth of Canada, and then maybe trying to see just what is the most interesting place in the world. But if I’m going to do all of that, then I want to be sure that I can twitter around the world without something in the back of my head whispering dark things about living out my retirement in a one-room apartment, watching The Price is Right on a TV that I bought at a yard sale and swearing at the neighbor kids for stealing the newspaper off my porch before I can get to it.

I guess it all depends on how you look at money. I’ve known people who don’t really consider it important, or who figure that it’ll come their way if they need it; I’ve talked to others who can’t live unless they’ve got three months of expenses banked at all times, never to be touched unless they absolutely positively cannot help it. I have friends who tell me their credit card balances, and I have others who might as well not have any money for how much they talk about it. For me, it’s how I build and preserve my lifestyle — if I don’t have enough, I am forced to either sacrifice something in my life or earn more money; if I have too much, I sock it away for some time when I might not have any, so that I can ensure I’m as close to where I want to be as possible.

I don’t consider wealth a victory, or even an accomplishment. It’s all in the application.

And believe me, if I won the pot tonight, I would no problem finding thirty million applications for it.