Abstract: Purpose – The purpose of this paper is to investigate the ways in which learning is contextualised among the intersecting worlds of education, training and work. Design/methodology/approach – A case study methodology is used. Findings – It was found that contextualised learning is integral to industry-school transition strategies in senior secondary school learning. However, its operational complexities are yet to be articulated in terms of senior secondary students as learners and earners – educational leadership in partnerships for future innovations in curriculum and pedagogy. Research limitations/implications – Initial analysis of first stage fieldwork data is reported. Originality/value – The paper is the first of a series that will report on findings from a three-year research project (2007-2010). Its originality stems from conceptualising “contextualised learning” (CL) for the development of individual capabilities through multi-directional and reciprocal boundary crossing among education, training and work systems.