This project investigated the interrelationships between family expectations and young people's post-school plans. The ten young people were achievers from The Smith Family's 'Learning for Life' program. All of the participants were from financially disadvantaged families. The research used interviews to understand these young people's perspectives of their transition experiences: the ways in which young people's school experiences impacted on their post-school pathways; how the young people weighed up costs and benefits in their decision-making; and exploration of the barriers and enablers encountered by the young people in their transition journeys. The findings endorsed the significant role played by families in young people's career decision-making and revealed some areas where such families might be provided with greater support.