The school where Chris Piccone teaches eighth-grade English maintains a desire to pull its community from its comfort zones to experience first hand the crushing poverty in the Dominican Republic. Although he always thought of himself as a bleeding heart, who was proud that he pushed his students out of their academic comfort zones, he realized that he wasn't ready to accept that himself. He gradually realized that, in order to continue engaging students, he also needed to be pushed into such new territory as the Dominican Republic. This article describes the Berkeley Preparatory School's mission service trip, and the author's life-changing experiences on the journey. Piccone writes about ways that this trip gradually wore away at his reluctance to face poverty and suffering head on, how he, his students, and colleagues, learned to acknowledge its existence, and how they recognized a shared responsibility for addressing poverty on a personal level.