Developmental cascades are links across the life span among heterotypic (qualitatively distinct) variables associated with one or more levels of organization within the ecology of human development. Using data from the longitudinal, 4-H Study of Positive Youth Development (PYD), we illustrate a developmental systems theory predicated model of cascades in the relations between individuals and contexts that promote positive development among adolescents. Consistent with expectations about the bases of PYD and the role in such development on person and context, ecological resources associated with parenting are linked to individual self-regulatory behaviors that in turn impact PYD, which is then associated with youth community contributions. We discuss the limitations and future directions of this research and the implications of developmental cascades for applications to policies and programs.