The transition from general education (e.g., high school) to vocational and tertiary education (e.g., college, vocational school) or to the labor market presents a number of developmental challenges. These challenges include making career choices and, more broadly, managing the transition. Coping with these challenges depends on the individual, their social network, and wider societal, cultural, and institutional conditions. This article discusses the informative value of developmental regulation, career development, and identity theories, for conceptualizing phase-adequate engagement at the post-school transition. Although previous psychological research has focused on individuals' career and transition-related engagement and its outcomes, we suggest this picture is limited because little is known about how young people's engagement is complemented and affected by the behavior of significant others and shaped by structural constraints and opportunities. Implications for future developmental research are discussed. (Contains 1 table, 1 figure and 1 footnote.)