Adolescents need to develop competencies to navigate an adult world that is complex and disorderly: a world of heterogeneous macro- to microecological systems containing contradictions and catch-22s. This exploratory essay examines adolescents' conscious processes of developing pertinent competencies for pursuing goals (agency) in these kinds of “real-world” settings. It draws on qualitative longitudinal research on youth's experiences working on arts and community projects in which they encounter the irregular dynamics of complex human systems. I describe how youth develop “strategic thinking”: executive skills for formulating strategies based on forecasting dynamics in navigating these systems. I also describe how youth learn to manage emotions (in self and others) that arise in these real-world transactions and how they develop motivation that sustains their work toward goals. Even as we learn more about the biological hardware of development, I argue that we must study youth's conscious, proactive processes in developing their own “software” to navigate complex and disorderly human worlds.