This paper discusses educator experiences of a Scottish university master's level study course designed to support the leading of professional learning. Scotland offers varied educator professional development opportunities, but these do not always transfer to pedagogy shifts and sustainable school evolution. For the research, course participants that are also full-time educators were interviewed about their experiences and recent approaches in leading professional learning. It was found that they have developed identities of professional intellectualism and activism within the course as a liminal space. However, they must also enact compliance to a system culture of rational thought and performativity whilst simultaneously attempting to disrupt the status quo for the perceived good of their staff and pupils. We consider their dilemmas and the influence of other actors in recontextualizing critically reflexive practice across a complex ecosystem undergoing reform.