Re-thinking the political workings of habit and habituation, this article suggests, is vital to understanding the logics and possibilities of social change today. Any endeavour to explore habit’s affirmative potential, however, must confront its legacies as a colonialist, imperialist and capitalist technology. As a means to explore what it is that differentiates contemporary neoliberal modes of governing through habit from more critical approaches, this article compares contemporary ‘nudge’ theory and policy, as espoused by the behavioural economist Richard Thaler and the legal scholar Cass Sunstein, with the pragmatist philosophies of habit offered by John Dewey, William James and Shannon Sullivan. While nudge advocates focus on how policy-makers and corporate leaders can intervene in the ‘choice architectures’ that surround us to outsmart or bypass problematic human tendencies, I argue, pragmatist philosophers appreciate the necessity of collective efforts to develop new and flexible forms of habituation in order to engender more enduring and democratic forms of social transformation.