This paper explores how loss is reckoned with in the wake of disruptive technological change in the context of on-demand rideshare. Spotlighting the turbulence that can occur when new technologies are introduced into mobility systems, the paper focuses a group of people who have lost significant financial investments as a result of the rise of on-demand mobility platforms to evaluate how a loss of investment is reckoned with as both a financial and existential challenge. Through fieldwork with owners of taxi licences in Melbourne, Australia, the paper builds on debates on affective investments within geography and beyond to argue that financial and affective investments are inextricably linked. For these investors, their financial loss precipitates the loss of affective investments expressed in terms of a loss of faith in institutions; a loss of face in terms of public respect; and a loss of conviction in terms of an inability to move forward with their lives. The paper argues that reckoning with these losses involves working on one’s capacities to act and sense. The paper concludes by drawing out some of the wider governance implications about transport workers and investors who will be likely be affected by loss in the coming decades owing to technological changes. David Bissell is Associate Professor and Australian Research Council Future Fellow in the School of Geography at the University of Melbourne. He combines qualitative research on embodied practices with social theory to explore the social, political and ethical consequences of mobile lives and technological futures. He is author of Transit Life: How Commuting Is Transforming Our Cities (MIT Press, 2018), and co-editor of Stillness in a Mobile World (2011), and the Routledge Handbook of Mobilities (2014). He is Managing Editor of Social & Cultural Geography and Steering Committee Chair for AusMob, the Australian Mobilities Research Network.