Growing up, I take for granted that I will one day be wealthy, too. To make or marry money was the natural trajectory for young women like me — women who attend prep school and a "public Ivy," who know how to tack into the wind and volley a tennis ball and keep their skis clamped tightly against each other. No matter how mortgaged my parents' lifestyle has been, I have apprenticed as a rich person for all my young life and am prepared to move into the position. But that's not what happens.
I give my wealthy girlfriends something, too. As a reminder of how the other half lives, I help keep them grounded amid charity auctions, private jet rides, and vacation plans that cost more than their kids' tuition. [...] Having me in their lives is proof that their kind of people aren't only rich people. And I allow them one of the great pleasures of having money — spontaneous generosity without guilt or expectation.