Jack was drawn to Teach for America. But he was torn. He felt the pull of a prestigious role on Capitol Hill, and the fear of falling behind peers who were headed to places such as Harvard Law School. Yet his most meaningful experiences in high school and college involved working on issues he cared about alongside the people affected by them—teaching math to inmates at a correctional facility, and advocating against the tobacco corporations that were getting his generation addicted to flavored e-cigarettes. A conversation with a Teach for America alumnus working in government sharpened his sense that proximity to problems matters. She lamented that many of the people around her were making policy decisions from “bubbles of power and prestige,” far removed from the communities touched by them. Jack chose the classroom.