Communities have their own set of cultural values that make their way into their classrooms and serve as criteria for the labeling of "insider" or "outsider." This article describes how critical empathy can allow the barriers between these constructs to be broken down as students are given the chance not only to listen but to see the world from another's perspective. Curricular strategies are detailed which encouraged the author's eighth-grade language arts students to use their final narrative reflection piece as a platform to practice empathic listening and critical empathy. In employing these three teaching strategies, students learned to be sensitive and empathetic listeners to insider and outsider perspectives as well as advocates for change in their community.