Abstract
This research focuses on the career transition from managerial to entrepreneurial roles and aims to explore the individual and contextual conditions that foster this transition. Financial crises coupled with globalisation have brought about a dramatic change in industries and related labour organisation models. Thus the skills required to adapt to new jobs are worthy of analysis by scholars. The results of this research show that Italian managers who have made a successful transition towards becoming entrepreneurs have a self-directed and value-driven approach to careers (protean attitude) in addition to a propensity to learn and openness to change (adaptability). These individual characteristics have been fostered by the work context present in their previous job experiences, in particular the managerial and HRM practices experienced by entrepreneurs when they were employed. The results of this study are promising in the light of the recent labour market reforms in Europe.