Americans have struggled to feel hope in recent years largely due to political divisions, but also due to the impact of the COVID pandemic. This chapter provides reasons for why hope has been difficult to achieve, including: the failed promises of political candidates, structural inequality, a narrowed sense of citizenship as personal responsibility, and the privatization of hope. It considers how the pandemic exacerbated many feelings of political hopelessness. It then turns to American pragmatism to offer a richer account of hope via the philosophy of John Dewey. This form of hope is better understood as a verb, hoping. It entails inquiring with others to find our way out of despair and to develop habits that support a proclivity toward ongoing action to improve our lives and those of others. This sort of action may lead to political dissent, because, as citizens focus on the improved world we desire, they may become frustrated with the shortcomings of the current world. Finally, this chapter describes how to cultivate habits of hoping in schools, providing one detailed example of such teaching in a higher education classroom.