This article explores how residents of a small coastal fishing enclave in Colombo live with cumulative waves of dispossession brought on by exclusionary projects of urban development. Drawing on ethnographic fieldwork, I introduce the analytic of navigation to describe how people move, plan and live with both present and future threats of dispossession. Navigation offers a unique perspective on questions of agency and resistance in oppressive conditions. Rather than framing subjects as “resisting” projects of world-class city-making, this analysis shows that urban residents instead engage in complex and occasionally contradictory modes of living with uncertainty. I complicate existing understandings of the term “navigation” by describing how questions of nation and belonging are crucial to comprehending how people navigate. Ultimately, I suggest that expressions of belonging and obligation to an imagined community might not only be strategic, but instead reflect some of the broader social forces which structure possibilities for action