One woman discovered the liberating power of taking a risk. BY AMANDA PRESSNER

WHEN I WAS 9, my parents decided that our family of four would skip all the warm weather traditions—pool parties, backyard barbecues, and sleep-away camp— and spend the summer taking a road trip across the country in a blue custom Chevy van. We hiked to the bottom of the Grand Canyon and panned for gold in Tennessee. Because I loved riding shotgun and shouting directions to the parent who was driving, I earned the title of Trip Navigator.