<p>This paper argues that contemporary visions of the digital future frequently sideline democratic politics, sometimes to the point of explicitly proposing post-democratic futures. These visions reflect a fundamental paradox arising from the conceptual tension between autonomy, as a political and ethical ideal, and automation, as a technological and economic imperative. Far from incidental, this paradox is historically embedded within modernity’s broader pursuit of control and rationalisation, and its salience is only increasing as digital systems automate forms of symbol manipulation and knowledge work hitherto considered the exclusive preserve of humans. This paper identifies key epistemological and discursive frames through which the relationship between autonomy and automation has historically been mediated. Looking back to the nineteenth and twentieth centuries, we foreground the crucial role of metaphor in shaping socio-technical imaginaries. Closer to the present, we address how discourses of datafication, smartness and artificial intelligence have fostered particular visions of the digital future – visions that present themselves as open to contingency, even as they lock us into paradigms that privilege financial speculation over democratic participation. We end the paper by reflecting on alternative models of futuring. If studying the digital past, present, and future teaches us to be wary of humanist discourses of rational individualism, it also suggests we should be suspicious of the intelligent systems and machine learning models to which we are increasingly expected to delegate agency. Against both paradigms, we call for forms of futuring grounded in embodied collective intelligence that acknowledge entanglement and alternative imaginaries.</p>