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Alyssa Mastromonaco, Former Obama Aide, on Her Unexpected Path to Politics

If I had a sense of myself in high school, I lost it in college. This was the first time I realized that money mattered and how you spent it mattered more, and since my family put value on getting the most out of your car—I thought Ford Taurus station wagons were aces because they lasted forever—I had no idea who I was. I grew up in a town where you didn’t know who had money and who didn’t. The wealthiest families were probably the equine veterinarians, and they drove beat-up Suburbans and Wagoneers. I don’t really remember anyone wearing makeup, save a little cover-up for sweet teen acne. I wore clothes from the Gap or Marshalls, and my hairstyle rode the wave from Magic Mushroom bowl cut to Eddie Vedder shag. (Think about it: When his hair was shorter, the layers were very similar to the Rachel.)