For Richer or Poorer: Wedded to a Life of Letters

Money is unfunny: The poor don’t chuckle about bills, titans like Donald Trump are humorless and, for most everyone else, finance is more of a sore spot than a punch line.

Despite all that—and despite its grandmotherly title—the new anthology Money Changes Everything is as funny as a lascivious sex column. Instead of CNBC analysts or C.P.A.’s, we get 22 gossipy and anxious writers, self-effacing thirtysomethings with a kid or a divorce and maybe a West Village brownstone, too.

Unlike the average taxpayer, most good writers are funny about money because they have only a little of it—but believe they’re just one best-seller away from lots and lots. And the ones who’ve already made it to the big time can look back with rueful humor at decades of Ramen suppers.

All writers, good and bad, rich and poor, have a pubescent boy’s sharply tuned self-consciousness: Their nerve endings are morbidly sensitized to envy and greed, anxiety and guilt.

Those traits make for excellent essays, especially when the envy, greed and guilt spring from real estate, that mesmerizing source of checkbook angst. Manhattan realty is the most psychotropic kind, so naturally half the accounts here revolve around New York co-ops or walk-ups or full-floor apartments.

Former Glamour magazine contributing editor Ruth Konigsberg wisely knows that Manhattan is the schoolyard where she’ll feel “like the poorest kid in the class.” She tells about the decline of her Upper East Side family, whose old-money fortune fizzled while she was still having sleepovers at the Dakota, where her friend’s brother had a miniature basketball court in his bedroom.

Even though the backdrop of Ms. Konigsberg’s story is a Sotheby’s auction, with the family heirlooms on the block, it’s hard to feel bad for her: Despite her destructively selfish parents, it turns out that her adult life is decorated with a husband, kid and big apartment. Not bad—but her great-great-great-grandfather was the banker W.W. Corcoran, whose name adorns the Corcoran Gallery of Art in Washington.

In fact—with the glaring exception of an essay about childhood abuse—it’s hard to feel bad for any of these writers, especially the basketball-court-in-the-bedroom kiddies. Ex–Paris Review editor Jeanne McCulloch grew up sneakily telling others that she lived on 73rd between Madison and Park, though she actually lived on Park Avenue, in a penthouse duplex. Poor little rich girl, forced to lie so young!

Unlike Ms. McCulloch, the real-estate heiress Isabel Rose had so many friends on Fifth Avenue that she never felt guilty about her own full-floor apartment. But guilt creeps up on you. Ms. Rose concludes her essay by insisting that she’s only “moderately wealthy”—yeah, sure, and she probably lives on 73rd Street.

New Yorker satirist Henry Alford is less coy, dubbing his purchase of an elderly neighbor’s apartment “manifest destiny.” Mr. Alford, a “pot-smoking, Joni-Mitchell-listening thirty-one-year-old gay man,” scolds himself for his apartment avarice, which he describes, mellifluously, as “a dark, sweet, criminal feeling.”

Then comes Daniel Handler, snorting magnificently at Manhattanite guilt: “My wife and I have lived in crummy apartments, and we could do it again if we had to. But we don’t have to. We don’t have to, and we are happier, no doubt about it, for not having to.” Happy Mr. Handler wrote the mega-blockbuster A Series of Unfortunate Events under the pen name Lemony Snicket. Now, he has an assistant who fetches his dry cleaning; now, when he earns $1,200 writing an essay on money, he spends it all on a single bottle of wine, which he shares with his poorest pals.

His delight in his good luck would be riotously irritating (like Ms. Rose) if he weren’t so riotously funny about the plunder (like Mr. Alford). Handler/Snicket writes like a 6-year-old who’s learned to fly and is joyfully telling his best friends what the blue skies are like, adding a drop of humility for their sake.

Though not every essay in the anthology is about New York, the city is its emotional and geographic core. Critic Walter Kirn, who acidly tallies the cost of romance, calculates the price of living in Montana with a college-age wife (now ex-) at “about one night a month with a non-English-speaking New York escort.”

Financial neurosis is global, of course. Even over in India, the “longing for land, any land” devolves into a Manhattan-like tri-generational fight over a family house. Short-story writer Meera Nair’s description of “property that would have helped her hold her head up high among her husband’s relatives” could be dropped seamlessly into Ms. Rose’s essay, or Ms. McCulloch’s.

And even in laid-back California, Fred Leebron feels “inspected” by the rich cruising by in BMW’s—“so obviously deprived, so disdained, so pitied.” When he moves to the South, to a better-paying job, he envies the perfect teeth glistening around him. Isn’t it good to know that Pushcart Prize winners sometimes feel deprived and unhygienic?

Glistening teeth shine in four other essays, including Marian Fontana’s delicate and austere meditation on the financial windfall from the death of her husband, a 9/11 fireman. When she meets the TV financial personality Suze Orman, Ms. Forman gets lost in her pearly whites. It’s a skillfully vague moment: Did the widow use some of her new money to whiten her own teeth? She can afford it now, along with a new chenille couch.

Embarrassment is the lifeblood of this anthology: embarrassment at having too much, at not having enough, at squandering it early, at not making a fortune, at wanting more in the first place.

It should be read by anyone who wants to make a living as a writer—or just make a living in New York. If you’re not scared off by the squirming anxiety and bad marriages and attacks of self-loathing—well, you deserve to become a big-name novelist in a nice big Bank Street townhouse.

Max Abelson writes Manhattan Transfers for The Observer.