As the field of planning stretches toward redressing the injustices of past land use patterns through reparative practices, student learning needs to include socio-emotional, as well as technical and intellectual, skill-building. Pedagogy should increase the planner’s ability to recognize systems of oppression and center lived expertise in decision-making processes. Transformational learning theory considers the mechanisms through which place-based learning expands student worldviews through exposure to other ways of knowing. Reflecting on a participatory action course through the analytical lens of transformational learning theory, this paper considers the pedagogical and ethical challenges and opportunities for planning education through collaborative action.