What enables success for students studying in the humanities can be a contested space; dependent not only on the view taken on the content and purpose of specific subjects, but also on the nature of teaching and learning. This paper examines the process of redeveloping an elective unit in a Tertiary Enabling Programme to prepare students for study in undergraduate humanities areas. The research involved consulting with academics from different disciplines in a regional university and analysing their views on what enhances student success. These discussions are reviewed in light of literature on best practice in teaching and learning for foundation and first-year university students, particularly exploring Pierre Bourdieu’s notion of extending ‘cultural capital’ while expanding ‘habitus’ to emerge confidently into the field of academic life. We conclude that fostering students’ awareness of personal perspective on historical and contemporary events, alongside encouraging awareness of the constructed nature of meaning in particular events is central to developing the kind of thinking valued by lecturers in humanities subjects.