Acknowledging the negative impact poverty and violence can have on the educational process, I explore ways in which a pragmatic interpretation of hope can guide us in formulating preventive and responsive measures that are not intrusive on the normal curriculum. I draw on key pragmatic ideas presented by John Dewey to emphasize the habits central to a pragmatic theory of hope. Equally important is the notion of a community of hope that fosters the development of hope’s habits. A hopeful pedagogy enables us to fund students with habits that help them resist the disconnection and despair that can come from living and learning amid impoverished or violent conditions. I argue that teachers can emphasize hope’s relevance to achieving the goals of the curriculum; they can also promote students’ self-knowledge through personal narratives that identify past accomplishments and explore possible means to desired goods. To begin ameliorating the tenacious conditions that foster poverty and violence, we need to look beyond the confines of the classroom and school to the resources and coordinated efforts made possible by the larger community. A pragmatic interpretation thus focuses our attention on individual and communal habits that help us secure desired goods. My discussion demonstrates at least some of the ways in which hope is a valuable resource for actively responding to circumstances that impede the educational process.