Innovation. Transformation. Disruption. These buzzwords suggest that the impacts of new technologies are all somehow revolutionary. Yet despite micro-disruptions to specific practices, new computing tools often fall short, reinforcing the status quo in new material forms. A smartphone appeals with the promise of working from the beach instead of the office; a worker breaks free from the office jail, only to be enrolled in expectations to be ever more available, on the clock even when supposedly on vacation at the beach. The oppression of the office has not been disrupted; instead, its reach has only expanded.The re-entrenchment of the status quo often entails the simultaneous reinforcement of inequity. Uber and Lyft transform the taxi industry. The consumer experience is more blissful than ever: A GPS-based app puts a car at your beck and call; no need to walk to a commercial corridor to hail a cab; no miscommunicated street crossings. Liberated from exclusionary licensing systems, anyone can be an independent digital entrepreneur driving on their own schedule. Uber even offers a subprime leasing program for drivers without good credit; payments are auto-deducted from a driver's paycheck; lessees lose the freedom to work on competing platforms or pursue other jobs; drivers sleep in their vehicles, work 12-plus-hour shifts, and default on their payments.Within the HCI community, there is growing interest in leveraging design as an agent of change in large-scale social challenges like sustainability, labor politics, and sexism. Yet the methodological repertoire we know is ill suited to the task. Practicing a traditional user-centered design process-one widely adopted in industry and taught in universities-would have us researching existing practices and needs in order to design technologies that might comfortably fit into existing routines. If we truly want to innovate, transform, and disrupt, we need new ways of working.In this article, we report on a set of conversations that grew out of a workshop held at DIS 2016 [1]. We explore how we might innovate in both method and outcome to design interactive systems that are responsive to current and future societal challenges. In contrast to user-centered design, we look for ways to design against the status quo, working to thwart the routines, habits, and norms of a social life that is inequitable and unsustainable.