The crises of recent years have engendered increasingly bleak visions of the future. This development challenges us to rethink our understanding of hope and futurity, and Marlene Streeruwitz’s 2011 novel Die Schmerzmacherin. takes an important step in this direction. Amy Schreiber, the novel’s young and existentially disoriented protagonist, trains at a security agency, learning to plan and control the future. But Amy keeps tripping over her own feet; her unsteady gait keeps throwing her off course. This article argues that Streeruwitz’s novel employs stumbling as an aesthetic device to expose the conceptual pitfalls of modern notions of the future. By discussing this poetics of stumbling, the article explores the double binds of modern security politics, the tensions between security and care, the unsustainability of societal expectations of success, and the subversive potential of errancy and failure. In Die Schmerzmacherin., stumbling represents an antidote to traditional utopian visions: a sober form of hopefulness that draws on the power of discord and disruption.