A pivotal theme (and discussion) in youth research is that youth transitions and young people’s perceptions of education and work is changing profoundly. The view is that the notion of linear, focused ’normal’ biographies increasingly is being outpaced by unpredictable, individualised and fragmented yoyo-transitions and ‘choice’ biographies (eg. De Bois-Reymond, Wyn&Dwyer, Beck). Drawing on two longitudinal research projects (Pless&Katznelson, 2007; Pless, 2009) based on both quantitative and qualitative data, in this paper I will focus on the factors that seemingly shape and influence young Danish people’s educational choices and pathways from primary school and onwards – focusing especially on ‘youth at risk’ in the educational system. The studies aim at understanding the young people’s narratives s and meaning-making in regard to education and more broadly their dreams and vision of the future (as grown ups). The longitudinal design furthermore makes it possible to get an insight into how the narratives– and not least the young people’s pathways – actually develop over time. Focusing on two of the young people’s narratives and actual pathways, I will illustrate some of the dilemmas and challenges that especially ‘youth a rick’ face as part of the life and educational pathways from primary school and onwards. Finally I will discuss to what extent the young people’s narratives can be said to support a movement towards choice biographies and yoyo transitions, or if alternative understandings are needed?