I discuss some of the biographical and historical roots of my lifelong interest in contexts of human behavior and development. These include experiences with youth problems related to broken families and jeopardized environments, as well as abrupt social change due to political turmoil (e.g., socialist system breakdown in Europe) and large-scale migration (e.g., to Germany and Israel). The culmination of many studies in various countries was the Jena Model of Social Change and Human Development. It brought together macro-level system change with individual adaptation of developmental tasks, and effects on well-being and other outcomes. The model placed perceived new demands in the middle (between macro change and developmental tasks), and conceptualized modes of developmental regulation (engagement versus disengagement). The results of such research underscored the relevance of multilayers of contexts for development and provided opportunities for scientific advice regarding public policy. They also informed interventions aimed at minimizing maladaptive development.