Starting from the Nordic policy idea of equal educational opportunities for all children and youth, this chapter examines the challenges and dilemmas that some young people from rural regions in Finland, Norway, Denmark, and Sweden faced when they transitioned from lower to upper secondary school. The chapter highlights how the structural conditions of living in a rural area often, but not always, complicated the young people’s transition, forcing them to set priorities and opt out of certain interests and educational ‘options’, thus enacting their agency in relation to restricted options. It further highlights the challenges of enacting agency in relation to societal ideas of what represents a ‘successful’ transition, balancing ‘not wasting time’ with ‘buying oneself time’ and ‘keeping doors open’. Overall, and thanks to longitudinal interview data, the chapter demonstrates how the challenges and dilemmas accompanying the transition to upper secondary school played out over time and how the structural, symbolic, and affective dimensions of enacting transitions were present in different ways in different times.