The complex interactions of social life serve to structure in time the opportunities, threats, and constraints that confront different social actors. This article examines policymaking within such complex “timescapes.” It does so by reference to the policy sciences literature and the complexity literature. The former is rich in its qualitative treatment of policymaking and time but has been slow to exploit the analytical tools of the complexity literature. The latter has been slow to appreciate the complexity of timescapes and to recognise the importance of power and the struggle for positional advantage. This article develops a synthesis of the two, combining their analytical power. It shows how this can illuminate the policy world, both conceptually and practically. It draws on Hirschman’s treatment of the “interlocking vicious circles” that hold development back and the “upward spirals” that can—when the time is right—be mobilised. It sets this within an appreciation of political economy and institutionalism. It concludes by considering the practical tools available for policy makers to navigate complex timescapes—and how the social scientist can subject those policy decisions to stringent scrutiny.