In this article, the author draws on a study of an after-school initiative serving inner-city high school students to describe and reflect on ways in which apprenticeship-like experiences support work on a variety of developmental tasks. The author describes key dimensions of the apprenticeship experience, discusses challenges faced by instructors, and reflects on possible effects on participants. Findings suggest that, in addition to strengthening discipline-specific knowledge and skills and, more selectively, skills needed for carrying out complex tasks, apprenticeship-like learning experiences have interesting self-effects. These experiences lead at least some apprentices to take more responsibility for themselves, to learn to attend more deeply, to learn about themselves, to learn that it is OK to do new things, and to learn that expressing one's thoughts, emotions, or doubts honestly will not have negative consequences. At the same time, apprentices' growth is tentative. Shifting habits, predispositions, and dominant feelings (about oneself and others) is difficult work. (Contains 3 notes.)