This article discusses After School Matters, a nonprofit organization that works with dozens of community-based groups across Chicago to connect teenagers with a vast number of opportunities in the arts, sports, technology, and communications. The 13- through 19-year-olds participating in After School Matters programs do not just sign up for sessions during the school year or over the summer. Most are hired as apprentices after a competitive interview or audition process. They receive stipends for their work, and they are treated as employees being trained to learn a very specific skill. The After School Matters apprenticeships that involve supervising and working with younger children provide an added layer of experience and responsibility for the teenagers. As paid apprentices, students also encounter a level of expectation from their instructors that they may not be used to at home or at school. While After School Matters has clearly provided a haven for many students who otherwise would be doing something less productive with their out-of-school time, the program is also helping teenagers discover talents and career aspirations that they might not have known they had.