As art museums increasingly commit to socially engaged practices that require critical ways of engaging with artworks, collaborators, and visitors, what does gallery educators' ongoing learning look like, and what motivates it? How does it inform or respond to change? Drawing on research with freelance gallery educators in Scotland, this article examines these questions within the overlapping contexts of the coronavirus pandemic and protests for racial justice in 2020. The tensions, challenges, and possibilities that emerged from participants' stories reveal complex relationships between professional learning, freelancer realities, and the adaptability required across the profession. In fleshing out how such a significant and unstable moment shaped professional learning, I consider what the field of museum education can learn from freelancers' experiences. Moving forward, how can we imagine futures that foster ongoing critical learning, sustained accountability, and collective wellbeing?