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While Dimon’s rudeness can be offputting, the sheer force of his passion and intensity can be irresistible. And that’s been the story of his life. “He loves misbehaving in places where he’s supposed to behave,” says his wife, Judy Dimon, who met him when they were fellow students at Harvard Business School. She vividly remembers the first time she saw him, at an HBS watering hole called the Pub. “The room was a sea of Ivy Leaguers in pastel Lacoste shirts, all grinning, all trying to win each other over,” she says. In the middle stood a Johnny Cash–style figure clad in black jeans, a black shirt, and black sunglasses. “He was sphinxlike, taking things in, not trying to be part of the group.” She recalls being astounded by his gall when, in the midst of a party she threw after they’d been dating for a few weeks, Jamie gave her a blunt ultimatum: “I’m going home, and I want you to go with me.” That she said yes–and that they’ve been living together ever since, for 26 years, and have three daughters, ages 16, 18, and 20–is testament to how endearing Dimon’s rough edges can be.
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Here are a couple of approaches that could make the transition easier: