This interdisciplinary paper brings together scholarship from the fields of education, psychology, sociology and performance to shed light on three pedagogy and learning strategies to support learners recontextualise knowledge between higher education and work contexts. These strategies include offering multiple different types of performance activities and modes of engagement with different types of people (learners/experts, different cultures, ages, etc.). Secondly, it provides spaces to fail and enables testing of personal strategies with limited risk. Finally, it supports students in connecting ideas and experiences from the past, across educational experiences of different performance practices and into wider contexts such as professional work.The research, which is a pilot, recognises the ways in which these strategies align with and operationalise Guile’s (2010) concept of recontextualisation, offering pedagogues tools to support learning in a similar way in which the concept of scaffolding might be seen to operationalise Vygotsky’s notion of the Zone of Proximal Development (ZPD).This pilot study uses semi-structured interviews and a thematic analysis approach with five graduates from an undergraduate drama degree programme in London. We recognise drama as a practical degree subject and as such consider our findings as generalisable to wider practical fields and disciplines, such as engineering and nursing education, and as having international relevance. The work offers a novel approach to conceptualising and evaluating the ways in which students deploy taught knowledge beyond the classroom, in work. It offers and augments arguments around the ways in which students bridge practice and learning from within the HEI and beyond it.