Young people's perspectives are not always central to policy and practice in widening participation contexts. This article explores enablers and barriers to educational progression by considering factors that young people suggest influence how they envisage and act on their futures. The underpinning study asked students aged 12-23 in disadvantaged areas of northern England to think about their possible selves using creative methods to encourage dialogue, including an animation and board game co-designed with university students. The findings suggested that students' perceptions of their own futures are influenced by their experiences of being categorised or labelled, both in and out of school, as well as the quality of their relationships with adults and peers. The authors discuss how these factors tended to shape the young people's experiences of being at school, with a view to rethinking labelling and enabling participatory spaces that cultivate the intersecting relationships, influences, structures and self-belief that make a difference.