Any future-oriented work, whether of academic or policy kind, needs a vision of the future, however vague. It is well known that such predictions are bound to be wrong, at least on the margin. The question is how to minimise that threat and make reliable assumptions. In this chapter we discuss a strategy of hypothetical retrospection. By imagining a future state of the world that is radically different from the present, we scrutinise hidden assumptions and suppositions taken for granted in (...) philosophical and policy visions of the future. More specifically, we discuss one example from political philosophy, which is John Rawls’s theorising about justice between generations, and three examples from policy, which are all from a Swedish context. We highlight some of the assumptions made in these disparate works, such as economic growth and acceptance of inequality. With the use of Tim Mulgan’s thought experiment of a ‘broken world’, where there are not enough resources to meet everyone’s basic needs, we, as it were, retrospectively assess the embedded assumptions. The main ambition is not to suggest that they are wrong from this perspective, but that the optimism they exhibit is not beyond doubt. (shrink)