62, president, the New School
I don’t need a beach. New York City looks pretty good to me. I’d want a house and a La-Z-Boy recliner with a little cup holder. I’d go down to Florida for spring training. I’ve been working since I was 14 or 15 years old—carrying papers, construction, restaurants, bars—so doing nothing is very appealing to me.
63, clothier, Peter Elliot
I’m starting up a geriatric gym. You cannot be a member unless you’re 75 and up. I’d get up at 5:30 in the morning, work out for an hour, do errands, but mostly I’d go out on the yacht to read.
62, owner and chef, Sarabeth’s
I’d stay on the Upper West Side if I can double the size of my apartment. The house in Lido Beach can be small as long as it’s clean. I’ll bake, but not as much as I do now.
I’d have a car and driver to take my husband and me to museums, art openings, and the ballet. And a nanny—a nanny for old people. We’d have a big house in the country with all our friends and all live together. I’d write a novel about that: a bunch of 70-year-olds who have a castle in France!
53, creative director, Barneys New York
My goal is to simplify, simplify, simplify. I see Jonathan Adler—my bloke—and me living in a totally chic hamster’s-cage-size apartment in New York with a couple of really nelly pooches to cuddle and zero possessions. I envision myself jogging Central Park in an insouciant leotard and leg-warmers with people screaming “You go, girl!” as I hobble past.
35, co-founder, Vice magazine
Most of the year is spent entertaining in a huge East Village apartment, going to events dressed like a fucking idiot, getting drunk in shitty taverns with people that are so funny you scream. The summer is spent in Quebec eating five-hour meals and swimming in Lac de Trois Montagnes with my kids and their kids (all yet to be born). The harsh New York winters get broken up by boat trips around St. Martin and farting through silk at Negresco in the south of France.
58, floral designer
I’ll turn over the management of my company to my wife, who’s twenty years younger than me, and spend Fridays and Saturdays at the track racing my Porsche.
27, police officer
When I’m 39, I’m gonna buy a big boat and fish. That’s it. Just fishing.
Estimated Number: $2,000,000
I’d like to stay in New York. I couldn’t be separated from my tailor. I’ll have to keep my house on Long Island because I need the closet space. I expect that when I slow down, I’ll use up the extra time by changing my clothes more often. I won’t be shopping a lot—maybe a murder case in the morning, the steam room in the afternoon—when you’re in your seventies or eighties, hopefully you’re wearing what you already have.
55, performance artist
My life will look like it did in my early twenties, free-floating, transient, and wildly creative. I’ll shuttle between New York, Los Angeles, Glasgow, and Rome. I have lifelong friends in all these places, so I won’t be paying for hotels. Travel will be tied into my appearances, so that’s paid for. Designers will be dressing me: There’s always a great affinity between young designers and ancient muses. Fans will take me to lunch and dinner. I will live on my $450-a-month Social Security check. There is no other plan. It’s the only way I can do it.
Estimated Number: $0
30, buyer, Kim’s Video
I’d like to have a home close to the park in Park Slope. I’ll see a lot of boxing in Atlantic City and take the cheap bus out there.
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