This paper explores the complex relationship between environmental education and researcher activism from the perspective of transgressive learning. With increasing interest within academia for more radical learning-based transformations for confronting sustainability challenges, come calls for more instrumental warrior stances in methodologies and research fields so as to more aggressively change ingrained unsustainable behaviour at the societal level. At the same time, in an increasingly polarized and unstable world, there is also a desire for more empathic learning approaches so as to build critical thinking and empowerment at the grassroots level through emancipatory learning. Based on case study research of a Colombian network of sustainability initiatives, this paper argues that key capacities of reflection, empathy, and courage are imperative in order for the transgressive researcher to address deep-seated socioecological challenges.