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Many qualitative interview methodologies presume participants’ circumstances are fairly consistent. However, in some cases, participants’ circumstances shift rapidly, calling for innovation in interview design that can adapt to uncertain event horizons. In this paper, we describe such an interview approach, which we refer to as reflexive longitudinal lifeworld interviewing. To illustrate this novel interview method, we draw on our own research with secondary mathematics teachers who shifted their teaching online during the COVID-19 pandemic. This paper contributes to the field of qualitative research by describing reflexive longitudinal lifeworld interviewing and its potential to better capture participants’ experiences in periods of heightened uncertainty.