Architecture’s presence in the city acts as a mediator through which the always already historical and social contexts are articulated. Architecture can influence our ability to give a comprehensive account of ourselves in the city. Our knowledge of self, our subjectification, is intertwined in the social conditions of our emergence. In effect, we make choices about which practices, or social actions, to enact based on their commensurability with regulatory norms. In many ways our everyday performances are explicitly tied to the presence of architecture. The purpose of this paper is to explore architecture’s participation in the maintenance of hegemonic discourses circumscribing appropriate uses of city space. To understand the effects of architecture on lived experiences I utilize the art of parkour as both a unit of analysis and as a method of investigation. Parkour’s engagement with architecture opens up a new understanding of the city. The data for this study came from several months of my regular participation in the parkour community in the downtown area of Indianapolis, Indiana. Therefore, I was embedded as much as possible in my field site interacting with other traceurs, conducting interviews, and being an active observing participant. To interpret and analyze the potential of parkour I take the position of the critical ethnographer. The purpose is to investigate how traceurs uncover new ways of understanding themselves, not only in relation to, but also in conjunction with, the architecture of the city. Through parkour, the self then finds its expression in the interstices of the knowable city.