The number of males entering higher education via an enabling pathway is slowly increasing; yet, males still battle with the anti-intellectual attitude that is prevalent in regional areas of Australia. Previous research undertaken by the authors began exploring the factors that inhibited or enhanced the male experience within an enabling course. This paper expands upon this research with a deeper focus on the male experience through personalised accounts derived from individual interviews. Using qualitative methodology and narrative inquiry, the findings provide a deeper understanding of the issues that males of different ages face when creating a new identity as a university student. This paper shares insights into what motivated the male students to enter university via an enabling pathway; the actual personal eriences both positive and negative during this time; and the effect that this commitment to study had on them personally and the people around them. The lens of transformative theory underpins this research through exploring frames of reference that align with the students’ experiences. Portraiture prose shares the individual stories which are analysed and the key findings extrapolated.