What happens when we shift from an explanatory to anticipatory mindset as a basis for social inquiry? How can we take a more deliberate approach to generating possible futures through research design and in situ sensemaking? What ethical possibilities emerge from taking a more proactive stance toward research as an intervention of future making? A ‘reflexive anticipation’ epistemology fosters experimental research design that intervenes as it explores possible trajectories. This framework is based in ongoing experiments training youth to be critical auto-phenomenologists of social media to speculatively intervene in their own data futures. In this paper, I discuss a five-year methodology experiment focused on these questions.