This paper examines the effects of changing modes of transition in a highly segmented education system that also provides designated spaces for the education of internationally mobile educational elites and future functional elites in the social fields of sport, dance, music, and art. It focuses on a—at least in the German context—little-researched example of the institutional modes of doing transitions available to students on such exclusive educational pathways in their transition from school to university or school to work. The results underscore that the provision of an excellent school infrastructure alone does not guarantee a promising career transition. How these career pathways are shaped depends crucially on the interplay between institutional demands, regulations, and spaces of opportunity and young adults’ biographical orientations and how they are embedded in different, milieu-specific spaces of experience.