Among contemporary fields of spatial practice, urban design, and governance have undergone particularly radical transformations thanks to the gradual incorporation of digital computation technologies. The most salient case of this resulting methodological shift is the Smart City paradigm, which exemplifies the conceptual framework championed by technocratic, data-driven approaches to the development of spatial intelligence in the urban field. This chapter argues that such framework is a problematic one: It operates under a decidedly top-down regime, and articulates mechanisms of representation that tackle the city as a singular “assembled whole” where individual subjectivities are averaged and the drawing (and subsequent controlling) of “flow” is foregrounded as an imperative of maximum optimisation. Taking an interdisciplinary approach that draws from the fields of Anthropology, Design Informatics and Urban Studies, this chapter asks the question: Is it possible to articulate data-based counter-practices that operate within the same computational plateau as Smart Cities, albeit explicitly subverting their narratives of optimisation, efficiency, and top-down “smartness”? As a tentative response this piece puts forward modes of collective intervention (developed as part of the author’s academic practice) that predate the technical overlay of the Smart City to leverage both individual and shared human subjectivities in the urban public domain through a DIY technological ethos.