Roots and Routes explores young people’s career expectations in three Danish island and rural communities: Bornholm, Mors, and the South Funen Archipelago, where young people face particular mobility-related dilemmas in relation to education. We explore how long-term career expectations are shaped in and by the local environment, focusing on family mobility experiences, local policies, and access to resources related to education, employment, and networks. Career expectations in rural areas are a key factor in addressing geographical inequality.