These papers represent continuing advances in the study of educational and occupational life-paths in psychology. In this commentary, I discuss the findings of each paper within a developmental systems theoretical framework. In doing so, I highlight the continuing need for psychologists to expand their view of the spectrum of psychological processes on the one hand, and the array of social environmental opportunities and barriers on the other, that co-contribute to how people make consequential life choices involving their education and careers. I conclude by discussing issues of agency, awareness, opportunity, and competing demands in assessing individuals' life choices; as well as the need for psychologists to study issues of equity in education in international contexts.