This article integrates life-course sociological insights and perspectives with the conceptions of agency and individual motivation formulated as the motivational theory of life-span development. We use Waddington’s epigenetic landscape as a metaphor for how life courses are shaped jointly by societal structure and individual agency. Social structure imposes constraints and institutions provide the transitions and pathways that together constitute critical scaffolding for life-course timing and path dependency (“canalization”). The building blocks from developmental and motivational psychology as well as from life-course sociology are introduced first. Then we address the dynamic interplay of individual agent and society in terms of life-span timing and life-course canalization (i.e., path-dependency) effects. The proposed conceptual framework moves beyond previous accounts of agent-society interplay in two distinct ways. First, we develop a systematically organized set of specific phenomena of developmental canalization on the one hand, and of institutionalized or social-structure based canalization on the other. Second, we offer a discussion of a set of scenarios that show how these specific psychological and society-generated processes may play together to shape individuals’ life courses and life-span development.