This chapter explores postdigital approaches to critically rethinking and dismantling grind culture—a relentless cycle of productivity and overwork. We explore pathways to resistance against grind culture by mapping out different forms of opposition and reform, relying mainly on theoretical explorations, but also illustrating these with both historical and contemporary examples. Central to our discussion is the role of digital systems in exacerbating grind culture, where the relentless pursuit of efficiency and optimization paradoxically often leads to increased work and more bureaucracy. To disrupt this harmful cycle, it is crucial to imagine and implement postdigital frameworks that challenge the constant strive for more productivity. Our speculative approach involves deconstructing existing technologies and imagining new paradigms that promote, for example, rest, meaningfulness, and individual and collective agency. The chapter draws on Foucauldian concepts such as ‘docile bodies’ and ‘technologies of the self’ to examine how power operates through the regulation of the body and both external and internalized disciplinary frameworks. It provides a tentative roadmap for reimagining ‘the machine’, advocating for futures where technologies take unexpected turns or breaks in directions that could make current productivity paradigms impossible.