Many teachers struggle to maintain or build hope among themselves and their students in today’s climate of high anxiety and low morale. This article describes and responds to those challenging con- ditions. It offers teachers and scholars of education a philosophically sophisticated and feasible under- standing of hope. This notion of hope is grounded in pragmatism and grows out of the pragmatist commitment to meliorism. Hope is described as a way of living tied to specific contexts that brings together reflection and intelligent action alongside imagination and gratitude. Such hope is realistic and generative, rendering it well suited for teachers struggling in schools today. The article does account for some school conditions, including fatalism, passivity, and lack of persistent motivation, that pose obstacles for achieving pragmatist hope. The article closes by describing specific actions teachers can take to build and sustain hope in their schools, including developing supportive communities of inquiry, cultivating habits of hope among students, and practicing confirmation.