Individualization has been a much debated topic in youth research for decades now. Getting a good education and choosing the right one is one of the manifold ways young people deal with late-modern individualization challenges. Based on in-depth interviews with 12 young students aged 17–20 years in the Danish Gymnasium we investigate how young people make sense of, and deal with, these challenges by focusing on how they handle and reflect on their educational biographies. We employ The General Activity Theory to sensitize our contextual understanding of individualization in relation to the youth perspective. Based on our data analysis, this study contributes theoretically by further-developing the concept of ‘strategic self-management’ in an educational context. We conclude that this concept is suitable for encapsulating how young people make sense of, and deal with, their educational biographies facing the new youth challenges. The study thus contributes with an enhanced sensitivity in relation to understanding some of the contemporary challenges of young people whose choice about education echo into their future work life.