Further Education (FE) is almost a new venture on the Maltese Islands particularly for UK NVQ Levels 1 and 2. In 2001 the Malta College of Arts, Science and Technology (MCAST) introduced the Foundation Certificate: A Further Education (FE) access course without entry requirements. Drawing mainly on the study by Ball, Maguire and Macrae (2000), Bourdieu’s habitus and structure (1977; 1990; 1993) as well as Evans’ bounded agency (2002; 2007) and Evans and Heinz’s (1993: 1994) transition types, this work explores the transitory experience of eight female students from Compulsory to Further Education. Between 2007 and 2010 these students narrated their experiences prior to entry at MCAST, as students on the MCAST campus, during their work placements as well as on their workplace. This book identifies three transition trajectories as well as a model for understanding the self in transition to FE within the Maltese context by identifying theories which are adaptable to this particular scenario. It also provides key learnings for policy makers and practitioners within the Maltese educational context.