The Official Preppy Handbook: Managing Those Dollah Billz

rainbow dollarThis is where things get complicated in the Prep lifestyle. If you’re serious about being a Prep, you’ve got to back up your rep with some serious cash, or at least the illusion of it. How do you create that illusion? Well, hopefully you don’t have to because you’ve got a trust fund. Barring that, you can cultivate an air of richness that you pair it with enough turtlenecks and an easygoing relationship with a credit card. Here are some do’s and don’t gleaned from the Handbook.

1. Don’t discuss your money. If you’re Midwestern, you’re probably already practicing this rule. You don’t say how much you paid for something. You don’t ever reveal your salary, if you do have to work, or the amount of your trust fund. If someone asks you a direct question about your money, murmur something about being sorry (for them!) and evade the question. Once you’ve eroded your air of mystery by answering money questions honestly, you’ve just cheapened your Prep brand. I’ve had people ask me directly how much I make per year at my job and my response should have been something along the lines of, “Oh, you poor thing!”

2. Of course it’s OK to discuss everyone else’s money. High times among Preps are spent sitting around with Mr. Gin and Mr. Tonic speculating about whether so-and-so made his or her money or inherited it. If only this kind of gossip session could be made into a board game, someone would be rich, rich, rich indeed. We all do this to some extent anyway, so speculate away but please, remember rule number one. Don’t get carried away and ask someone how much it cost to rent that house in the Hamptons or how much they make at their job as Executive Director at Angel Wings of Hope For a New Day For People Living With High Spirited Toddlers.

3. Give to charities that feature your name in an annual report or in the program for a big event. It’s best if the publicity doesn’t break donations down by level so that everyone is left wondering just how much you gave (see 1 & 2). Even if you gave $100, not $10,000, you’re cultivating an air of someone with disposable cash and an empathetic heart. People with time and money to give to charities are seen as being “set” in their own lives and so more able to focus on the problems in the lives of others. Not sure what to give to. Literacy is a good, blanket cause, as is any disease or affliction, especially if it’s happening to people in a country other than yours (see Bill & Melinda Gates and their crusade against malaria. Yes, a very good cause and there is a real need for it, but notice that it also meets the Prep criteria and B.G. is nothing if not a big Prep, albeit smarter than the average Prep and unable to hide his income/worth, which has been published more than photos of Britney Spears at her most nightmarish.)

4. Keep people guessing. Spend a lot on a designer coat and then insist on driving to an Indian reservation for discounted cigarettes. Buy season tickets to the Opera and then only go to two performances, giving the rest of the tickets away or, even better, forgetting about the Opera season altogether. Spend an enormous amount of money on a Eurpean “tour” and then get crazy in the duty-free shopping area of the airport. Host a lavish dinner party but cut coupons out of the Sunday paper to give to your live-in help for grocery shopping. Even better, grocery shop yourself in jeans and a sweatshirt but wear your diamonds as well.

5. Don’t carry cash with you. Ask to borrow cash from friends for things like parking, getting a coffee, etc. Or charge tiny items, like a candy bar.

6. Insist that your children live modestly and give them a small allowance for doing chores. Then buy them big gifts on a whim.

7. Never replace anything until you’ve exhausted all avenues of repair, part replacement, rehabilitation. You’re the guy in the threadbare sweater pulling up to the upholstery shop in your new Volvo with a Queen Anne wingback chair needing repair tied down in the back.

8. Don’t say wealthy, as in, “He’s a very wealthy man, isn’t he?” Use rich instead, as in, “He’s filthy rich, isn’t he?”

9. Take on debt. It’s the only way you’re really going to make it as a Prep unless you have an incredible trust fund. Don’t go so far into debt that you can’t live day-to-day (if you have to go into debt counseling or consolidate your debt, your days as a Prep are over) but don’t be afraid to charge that trip to St. Barts, either.

So much of the way we think about and handle money has to do with our value systems. It’s of utmost importance that your values fall in line with other Preps. First, you want to value sameness. As in, each year you ski in Vail over Christmas (and, yeah, you do call it Christmas)  and each year you chair the committee for the Save The Kitties Gala Ball. Even better, this is what your parents did and this is what your grandparents did. You DO NOT take up new sports, like frisbee golf, or go to Dubai just to see what everyone is talking about. You stick with the tried-and-true – like regular golf. Of course you golf! And play tennis! And ride a horse!

But don’t get too excited about it all. You value being low-key and nonchalant. You value charm and understatement. Nothing to see here, folks, move along. As scanalized as you may be when your married friend Muffy makes out with very-married Kip at the club holiday party, you must resist your urge to blabber on about it. Better to dismiss the incident with a muttered comment, like, “Fools!” or “It’s a bit early in the season for cabin fever, isn’t it?” than to lose your head about it because you were hoping to hook up with Kip yourself.

Luckily, drinking is big on the list of values, too, and this will help you get through the above. You can’t go to a party and stand around with empty hands or, even worse, a glass of sparkling water. It isn’t done. And rehab is for sissys. After F. Scott Fitzgerald finished a rehab program, Ernest Hemingway told him he might as well toss his balls into the sea, if he had any left. That’s the spirit, Ernie!

When you’re not drinking, you should be participating in some kind of sport (lots of choices here – golf, skiing, golf, tennis, horse back riding (say “equestrainism,” please), golf, golf, more golf). Whatever you do, don’t take up running, for Christ’s sake. It’s much too hard on the body when one is always hungover.

All of this does require a bit of discipline, greatly admired among Preps, and public spiritedness (i.e. volunteerism). You can’t always being drinking and enjoying a day on the courts. You must set aside a few hours each week to do something for the Red Cross or to teaching children how to read. Otherwise, how can one live with oneself??

So where does this leave me? In need of a charity to support (I like reading, so literacy might be a good one) and a higher alcohol tolerance. If you see me at the library, teaching low-income kids to read while wearing my cashmere sweater set and reeking of gin, don’t be afraid to stop, say hi and set a time for brunch on Saturday. Sunday brunch? Oh, you poor thing!

One thought on “The Official Preppy Handbook: Managing Those Dollah Billz

  1. 2 words: Betty Draper – I wonder if there might also be something in this book about no matter what age you are, you must refer to your father as “Daddy”…?

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