Art museums are increasingly responding to calls for exhibitions, community engagement, and institutional changes that confront and unsettle taken-for-granted knowledge, structures, and ways of working. Grounded in such a dynamic and evolving field, this qualitative study asked the following: What does gallery educators’ own learning look like -- and what motivates it? How does ongoing competency building inform critical dialogue with visitors and support wider efforts to reshape the field through an ethos of social justice? Drawing on tenets of critical pragmatism, transformative adult learning, and constructivist grounded theory, my thesis comprised three manuscripts based on findings from two series of interviews with gallery educators in Canada and Scotland. This article highlights my findings, contextualizing my analyses on the shifting ground shaping gallery education in both countries. In doing so, it contributes to both a relative paucity of scholarly research on critical professional learning in art museums and an emerging body of literature addressing the impact of the coronavirus pandemic on the working lives of gallery educators and the futures that lie ahead.