How can design orient people to an expanded sense of future possibility? Design researchers are beginning to recognize design’s potential role not solely in producing products, services and strategies but, instead, in shifting mindsets and behaviors. This shift requires a different view of the design practice, from engaging users to gather insights to be implemented, to that process as the actual material of the design. Borrowing from the framework of practice-oriented design, a first step in these processes is expanding participants’ understanding of future possibilities. In opening future possibilities, one recognizes an expanded range of futures and, ideally, engages in dialog with other people and their range of possibilities. This paper introduces mapping activities that are intended to reframe participants’ perception of possible futures. This study conducted pilot workshops with participants who were downsizing their home and struggling with decisions about their things and spaces. This paper argues that working with people already engaged in life transitions such as downsizing presents a rich opportunity for these futuring methods, as they are already beginning to grapple with designing for possible futures. These methods provide a stake in the ground for future exploration of potential methods to engender mindsets of possibility and engage in trialing methods like living labs.