In this chapter, we highlight the transition to upper secondary school among young people in nine Nordic rural regions. Like other young people in today’s Western world, they grew up with expectations of rapidly achieving successful careers which will benefit them individually and as a society. However, living in rural areas with relatively fewer educational opportunities or being at the margin of the educational system (as was the case for the study conducted in Denmark), they found themselves in the cross-pressure of different and somewhat contradictory expectations. The aim of this chapter is to explore the challenges and dilemmas associated with transitioning to upper secondary school in particular as we follow this process over time. The research question is, what typical reflections, negotiations, and concerns arose early in the process of deciding which upper secondary programme to choose when the deadline came closer, and what typical struggles emerged after the decision was made?