Beginning with some reflections on Nietzsche’s demand that we learn new habits of thinking and willing, ones that will enable us to affirm the past as that which we willed, the focus here is on changing our own habits as regards the question of habit itself. Using the Slovenian dancer Jurij Konjar’s reimprovisation of Steve Paxton’s original Goldberg Variations improvisations as a case study, this essay provides a commentary on the documented correspondence between Konjar and Paxton. The central issue addressed here is Paxton’s desire to ‘outwit’ his habits of performance and Konjar’s ultimate acceptance and affirmation of his own. Countering the dominant antipathy to habit in the discourses on improvisation, this chapter argues for a deeper engagement with the essence of the habitual as the locus for a consideration of the very event of dance, understood (by Paxton) as having a ‘life of its own’ above, beyond, or outside the habitual structures of the performing self.