In this original contribution to the American philosophical tradition, Patrick Shade makes a strong argument for the necessity of hope in a cynical world that too often rejects it as foolish. While most accounts of hope situate it in a theological context, Shade presents a theory rooted in the pragmatic thought of such American philosophers as C. S. Peirce, William James, and John Dewey. Shade first discusses the particular hopes we pursue and then turns to the habits of hope - persistence, resourcefulness, and courage - that are vital to their realization. Indeed, habits of hope are the basis for developing hopefulness, a complex habit that nurtures and sustains us even when we fail to realize particular hopes. Hopefulness, Shade maintains, enables us to avoid the paralysis of despair. Throughout the discussion, Shade gleans insights from a variety of sources, most notably John Steinbeck's The Grapes of Wrath and Stephen King's novella "Rita Hayworth and the Shawshank Redemption," but also from the real-life experiences of such heroes as Cedric Jennings and Martha Manning. These examples embody and illuminate the concept of hope and offer incentive and illustrations for developing a hopeful life. Shade's account shows how we can make hoping practical without forfeiting its unique capacity to help us grow.