This paper considers ways in which a performed drawing practice, in the form of contouring, can serve as a catalyst for social engagement. The paper will contextualize iterations of an art practice performed by Shepley over the past three years focusing particularly on varying aspects of gesture as a spatial practice. Citing projects which reimagine neglected sites in order to rediscover a city’s cultural and artistic potential through imaginative transformations, the paper will discuss drawing as gesture; a means of encounter; a method of speculative enquiry relating art to everyday practices; a means to prolong the notion of artistic activity and a more socially engaged practice; a form of occupation within the field of distribution; activism and game playing; dispersal and provocation; ambivalence, uncertainty and delayed closure. The paper examines ways in which the gesture of sweeping within a public space can help to disclose potential breaches in the cultural infrastructure. The paper will establish how such projects are part of a broader tendency highlighting the potential of creative indeterminacy to, push away from ‘art’ and to restore an embodied relationship to the world.