The case of the early imperial small rural settlement of Marzuolo, in south-central Etruria, paints a micro-history of arrested developments: a couple of decades into the site's existence, an abandoned wine-production facility was converted into a blacksmithing workshop, which in turn burnt down and was abandoned soon after. But were both these endings failures? This article uses the concept of failure as an epistemic lens to examine inequality: who could fail in the Roman world, and for whom was failure not an option? It argues that failure was tied up with particular notions of the future, which were not equally distributed. Yet in contrast to modern paradigms, in the Roman world even the privileged seem not to have embraced failure as a stepping-stone towards growth.