Scholars writing on agency argue that normally, individuals who experience social structures as comfortable will tend to want to reproduce them while those who experience these structures as oppressive will want to change them. This is a bleak outlook because it suggests that those in positions of power and influence are less likely to seek to overhaul the very system of rewards and punishments that benefits them. However, there are exceptions to this pattern: instances where those who experience the structures as comfortable, nevertheless, work at transforming them. This article introduces an alternative perspective to current transformation discourses by seeking to understand why such exceptions exist. It argues that critical engagement is an important dimension of such transformation, and examines how it interacts with reflexivity to shape individual choices and reformulate interest. Drawing on a hermeneutic phenomenological analysis of in-depth interviews with 10 academics who have been identified as agents of change at one university in South Africa, we reveal how individuals are able to shift their understanding of what is or is not in their interest in a context where raced, gendered and classed interests are deeply embedded in the fabric of the society. In such contexts, reflexivity and critical personal engagement with one's context can lead to a shift in interest and then consciousness as the individual comes to see and experience things from a different vantage point, opening up the possibility for a changed relationship with the social structure and its constraints and determining influence.