This article presents outcomes of two studies which focus on the lived experience of transition by students entering higher education in NSW (New South Wales), Australia, from two divergent pathways: Technical and Further Education (TAFE) and a university based enabling program. The studies intersect in two fundamental ways. First, the theoretical foundations (Mezirow’s Transformational Learning Theory and Bourdieu’s Social Capital Theory) which emphasise the role of habits of mind and the habitus respectively in an individual’s life. Second, both studies have identified the primacy of the contribution of education to changing notions of self. The studies have found that successful students reappraise and reimagine their self-identity inclusive of possible future selves. The studies reject deterministic and often deficit models of socio-cultural influences on self-concept, and instead embrace the perspective that adult learning can not only realise, but also build upon latent capabilities, and ultimately that it is an empowering experience for many transitioning students.