Many overspenders are driven more by self-worth than net worth, believing they attained their lofty perches because they are innately deserving. Their bank accounts may be shrinking; their self-regard isn't. "They think they can't be expected to handle money in the same way," says Jerrold Mundis, a financial counselor who works with affluent individuals and is the author of Earn What You Deserve. Beyond that, they have no desire to be fiscally responsible—that would shatter the image they've so carefully cultivated. Mark, a 41-year-old executive at a high-end home-furnishings company, fell into debt despite his six-figure salary because, as he says, "I'm constantly treating myself. I don't believe in self-sacrifice—I have a sort of moralistic self-righteousness that I deserve good things. And because I'm surrounded by luxury all day, I know what's good quality and what isn't."

Likewise, Paul views his Hamptons home as a monument not to wealth but to hard work. "It's the physical crystallization of a certain kind of dream," he says. But he admits he's questioned the wisdom of his ways. "There's an element of total insanity. It's been a leap into the void. I keep saying to my partner, 'Can we really do this?' It's such a lot of money, and it's actually not necessary."

Having watched a certain Orson Welles film on a recent flight from Hong Kong to New York, Paul had a realization. "There's something Citizen Kane–like about why you surround yourself with all this stuff," he says. "I thought, when we die, someone's going to inventory everything." Depending on your outlook, that can prompt you to reevaluate your priorities—or to buy yourself a shiny new Rosebud.

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