This research examines how youth in arts and leadership programs develop skills for organizing actions over time to achieve goals. Ethnically diverse youth (ages 13–21) in 11 high-quality urban and rural programs were interviewed as they carried out projects. Qualitative analyses of 712 interviews with 108 youth yielded preliminary grounded theory about youth’s development of strategic thinking, defined as use of dynamic systems reasoning to anticipate real-word scenarios and plan work. Strategic thinking appeared to develop through youth’s creative engagement with tactical challenges in the work and feedback from the work’s outcomes. Program advisors supported this development by giving youth control and by providing nondirective assistance when needed.