This paper offers insights into the increasing dichotomy that exists between official forms of opportunity and access and the actual "lived experience" of young peoples' trajectories towards careers in the UK's market-orientated Sport-Fitness and Physical Education employment sectors. It does so by drawing on data generated by an 18-month ethnographic study to provide a case study of two students who chose to make the transition from a Foundation Degree in Sport Coaching (FdSc) onto a "Top Up" Bachelor of Science (BSc) Sports Science and Coaching qualification. The paper illustrates their experiences of this transition in relation to the following phases of their trajectory (1) "facilitators of transition"; (2) "managing expectations"; (3) "transformation"; and (4) "isolation." The findings highlight how, for some individuals, current transitions facilitate a critical distance between individual dispositions towards education and the positions and practices of higher education. We suggest that education and employers must further listen to the voices and experiences of students that transcend the rhetorics of official policy discourse to facilitate a process in which the conditions of transition may begin to be reimagined.