Learning organized by participants in activities outside of schooling is often uncommonly successful. In this chapter, research is described from the MultiMedia Works after-school club for underserved middle-school students from a multicultural community. The design of the club is guided by results of studies of non-school learning from anthropology and sociolinguistics, which are integrated for the purpose of identifying organizing principles important for engaging and sustaining successful learning. The club is modelled on properties of successful learning, and its activities include the use of state-of-the-art computer tools designed to exploit special properties of multimedia representations that foster conversation, representation and socially-focused learning. I contrast the organization of learning in the club to that found in traditional classrooms, and to conceptions of learning found in current developmental psychology theory. I conclude with characterizations of the successful dimensions of the activity for learners and their implications for the design of learning environments.