Movement pedagogy researchers claim that people’s existing ways of moving influence their possibilities for developing new movement capabilities. Relatively little research, however, has focused on how movement habits influence individuals’ learning in new situations. The aim of this investigation was thus to provide and understanding of how individuals’ movement habits can affect their learning in novel learning situations. To achieve this aim, we developed an investigation with 11 preservice physical education teachers in two phases. The first phase involved examining the participants’ movement habits and involved the production of data through: (1) a qualitative movement analysis session that contained ten movement tasks and that was video recorded, (2) semi-structured interviews based on the participants’ movement backgrounds and responses during the movement analysis session, and (3) an open survey containing questions related to the participants’ experiences of movement learning. The second phase involved examining how the participants developed new capabilities in a novel movement learning situation. The novel situation involved the participants exploring the practice of unicycling for 1.5 hours per day for five consecutive days. In the second phase, data were produced using three methods: (1) observations conducted using video cameras and video conferencing software, (2) ethnographic-type interviews focusing on the participants’ ongoing experiences of unicycling, and (3) participant diaries that participants logged electronically on the university’s online learning platform. In this paper, findings from two participants are presented as case studies using Shilling’s (2008) work on habits, crises and creativity as an analytic framework. Habits are understood as are acquired predispositions to respond to environmental conditions in certain ways. Crises are situations where a person’s habits no longer provide an effective way of interacting with the world. Creativity is understood as the actions undertaken to resolve crisis and regain effective ways of interacting with one’s environment. The two cases demonstrate how different sets of movement habits can interact with novel tasks, making the occurrence of crises and the demand for creative action, more or less likely. The cases also demonstrate how subjective and physical elements are interwoven in the experience of crisis. Finally, the cases provide insights into potentially productive habits for movement learning. The paper is concluded with pedagogical implications, including a consideration of how crises might be managed in educational contexts.