This article analyzes the development of initiative as an exemplar of one of many learning experiences that should be studied as part of positive youth development. The capacity for initiative is essential for adults in our society and will become more important in the 21st century, yet adolescents have few opportunities to learn it. Their typical experiences during schoolwork and unstructured leisure do not reflect conditions for learning initiative. The context best suited to the development of initiative appears to be that of structured voluntary activities, such as sports, arts, and participation in organizations, in which youths experience the rare combination of intrinsic motivation in combination with deep attention. An incomplete body of outcome research suggests that such activities are associated with positive development, but the developmental processes involved are only beginning to be understood. One promising approach has recorded language use and has found that adolescents participating in effective organizations acquire a new operating language that appears to correspond to the development of initiative.