Policy-makers and researchers, unless they believe in moral decline as an explanatory principle, are forced to make use of psychology in order to explore disaffected youth behaviour. Usually this is an intuitive psychology of cause and effect; so there will be an increasing call for formal psychological investigation in order to understand youth experiences, attitudes, and wellbeing. We seek to extend this approach to understanding the process of integration into higher education institutions, since education is key to current aims to build social inclusivity. In this paper, we present findings on young people's self-esteem, anxiety, and ability to cope in a group for whom disadvantaged backgrounds and first-generation entry to higher education are frequent. Using extended narrative accounts, we combine studies of subjective experience with these formal indicators of well-being and sense of personal empowerment. We outline a longitudinal programme for studying young people as they move into higher education, and offer our results as a contribution to understanding (a) the relationship of social transition to health-related outcomes for individuals, and (b) dynamic interrelationships of youth behaviours and perceptions, and (c) social and individual factors in adjustment to higher education. For example, initial data suggests some evidence of disengagement and poor coping strategies.