The transition from school to work is a central developmental task with long-term implications for the financial and social status of individuals. We argue that dynamic adjustments of aspirations play a decisive role for a successful outcome of the school to work transition, particularly in the context of the German vocational training system. Latent growth curve analyses conducted on the self-reported occupational aspirations of German adolescents (N = 414) surveyed in a 5-wave longitudinal study during their senior school year support this assumption. Based on expectancy-value-models of achievement, we delineated an adaptive trajectory of aspirations as starting off with relatively high aspirations and subsequently gradually downgrading them until s is attained. Such a trajectory of adjustment should maximize both expectancy (i.e., probability of obtaining an apprenticeship position at all) and value (i.e., training position with promotion potential). Finally, we showed empirically that the trajectory conceptually proposed as most adaptive was characteristic for youth who reported phase-adequate goal engagement strategies as suggested by the life-span theory of control. (Contains 3 tables.)