While much has been written about the transformative potential of adult education from the student’s perspective, little research has been done into the experiences of those who teach in such contexts. This paper draws on the reflections of three academics who work in an enabling program in regional Australia. We embarked on a process of critical self-reflection, not unlike the kind of activity we ask of our students, as we considered the challenges, as well as the rewards, inherent in our experiences. Brookfield’s (1998) concept of critical reflection was used as a vehicle for examining underlying assumptions about what we do and how we are positioned within the broader University community. Though we are cautious about describing our learning as ‘transformative’, we contend that the process of critical reflection has led to a heightened awareness, and has enabled us to articulate perceptions of professional and personal growth.