Despite considerable quantifiable data about the circumstances of care leavers in the United Kingdom, there is less qualitative data about how these circumstances are experienced. This article is underpinned by positioning theory, with a particular focus on the unfolding personal narratives of young care leavers in relation to their mental health and wellbeing and the role of a life‐skills programme in supporting them in this respect. The research illustrates that leaving care projects, such as the one in the current study, are more focused on employment and housing issues than on addressing the mental health and wellbeing needs of young people. Our analysis of interviews with young people illustrates the ambiguity of understandings of concepts such as “mental health” and “wellbeing,” and the complexity of responses to questioning around this area. This illustrates one of the major problems in evaluating the outputs and outcomes of such projects in terms of simplistic targets, where mental health and wellbeing are not clearly defined or understood by young people themselves. The current research provides a more complex picture. More research is needed that involves in‐depth and longitudinal assessment of specific mental health needs of care leavers and how they can be addressed successfully.