Higher education is understood to play a critical role in ongoing processes of social transformation in post-apartheid South Africa through the production of graduates who are critical and engaged citizens. A key challenge is that institutions of higher education are themselves implicated in reproducing the very hierarchies they hope to transform. In this paper, I reflect critically on my experiences of a course aimed at transforming teaching through transforming teachers. In this paper, I foreground my own positionality as a white female educator as I draw on feminist theorising to reflect on my experiences as a learner in the Community, Self and Identity course. I suggest that we need to teach in ways that are more cognisant of the complexities of the constraints on personal freedom in the past if we are to contribute to the development of social justice in the future.