This chapter is concerned with the experiences of non-traditional participants in higher education for whom, until recently, the very idea of obtaining a degree was an impossibility. The opportunity of entering institutions of HE has consistently eluded their school friends and family members. The circumstances leading to their entry into HE, the experience of HE itself and its aftermath left them facing a ‘different’, though not in every case a certain, future. ‘Border crossing’ (see Vincent, this volume) into the predominantly middle-class arena of the university threw into sharp focus the degree of instrumentalism and drift deployed by individuals, both in terms of decision making and as a coping strategy. It is suggested that in retrospect, those with instrumental tendencies are more likely to achieve desired outcomes, whereas others who study various subjects for the sake of self-improvement and knowledge acquisition per se, find themselves drifting into a disconnected, ambivalent world outside the university. The consequent disillusionment can be directly related to the type of degree obtained as well as the perceived status of the HE attended. The notion of ‘success’, which remains problematic for traditional nonparticipants in HE, is presented reflexively and as requiring careful consideration.