This article describes the different experiences of the participants in an Outward Bound-sponsored "urban expedition" to New York City that was designed to make them better teachers by examining their beliefs and biases. The participants in this "urban expedition" came from schools that work with Outward Bound USA, the Garrison, New York, nonprofit that has led wilderness and ocean expeditions for four decades. It partners with more than 125 such schools, many of them charter and alternative schools, to offer a hands-on, expeditionary approach to learning. Participants in the program described here were teachers at schools that use the Outward Bound model. Driving all Outward Bound ventures is the notion that great learning happens through leaving a safe, everyday environment and taking on new challenges. Trekking through four of the city's five boroughs, often for 15 hours a day, the teachers were immersed in activities as diverse as visiting a Sikh temple, talking with students, learning salsa dancing, climbing a ropes course, and handing out sandwiches to homeless people in a park. Even the simplest activities were designed to put participants in unfamiliar situations, with the hope that by risking failure or discomfort, the teachers would develop more empathy for their students, who are being asked to do just that every day.