The COVID-19 pandemic has disrupted the international medical education community in unprecedented ways. The restrictions imposed to control the spread of the virus have upended our routines and forced us to reimagine our work structures, educational programming and delivery of patient care in ways that will likely continue to change how we live and work for the foreseeable future. Yet, despite these interruptions, the pandemic has additionally sparked a transformative impulse in some to actively engage in critical introspection around the future of their work, compelling us to consider what changes could (and perhaps should) occur after the pandemic is over. Drawing on key concepts associated with scholar Paulo Freire’s critical pedagogy, this paper serves as a call to action, illuminating the critical imaginings that have come out of this collective moment of struggle and instability, suggesting that we can perhaps create a more just, compassionate world even in the wake of extraordinary hardship.