The euphemism "21st century contexts" is often used to capture the transition from solid twentieth century education towards more uncertain social and educational conditions. These contextual narratives acknowledge the complexities of contemporary education that make decision-making, professional practice and leadership seem difficult. But they rarely explain the context of uncertainty, which, as research suggests, is linked to rapid change in practices of governing and their effects on nation states, the inter-state order, and established national educational knowledge-authority orders. This disjuncture raises questions about how, and with what effects, contexts shape educators ways of knowing and doing education. I use the concept of "educational space-time" to understand how educators contextual understandings are implicated in educational change by drawing examples from studies of educational change in different historical periods and governing regimes. I argue that the way educators navigate change and uncertainty has effects on learning and citizenship but should also acknowledge the effects of changes in governing regimes. Contextual understandings that acknowledge shifts in governing-learning regimes can open the way to educational work that is not locked into binary choices between territorial government or multilateral governance.