Recent advances in artificial intelligence (“AI”) and robotics have rekindled fears of a workless future. In the aftermath of the COVID-19 pandemic, in particular, dystopian headlines portend that a robot apocalypse will “steal”, “kill”, or “destroy” humans’ jobs on a mass scale, thereby framing automation as a threat that must be counteracted by law and policy. Conversely, drawing on Aristotelian moral and political philosophy, the prospect of automating human work through AI and the consequent vision of a flourishing-centred, post-work society emerge as not merely acceptable but actively desirable. Nonetheless, this vision of a society in which AI liberates humans from toil, allowing them to engage in those activities that they deem intrinsically valuable, risks being labelled as “utopian”. To counter this objection, this paper advances four claims that seek to highlight the value of utopian thinking while questioning the very labelling of the purported post-work society as “utopian”. In the event that these four claims are accepted, however, the objection that the construal of a flourishing-centred society as of interest to the legal order would itself be utopian remains valid. For this reason, this paper resorts to “virtue jurisprudence” or “the aretaic turn” in law. As a normative theory that invokes Aristotle’s ethics to address key questions in law, virtue jurisprudence argues that the law should aim to ensure the necessary preconditions for human flourishing. Applying this theory to the “future of work” debate yields the question of how AI automation would be regulated if human flourishing were, indeed, the law’s ultimate objective. The paper concludes that, far from being neutral, pejorative characterisations of future scenarios as “utopian” should not be taken at face value, particularly in relation to the “future of work” debate. Rather, political and legal argumentation must provide space for imaginative, utopian considerations alongside more realistic or pragmatic ones.