Youth programs that meet during the out-of-school hours, particularly those offered by organizations that have historically collaborated with their community members to support their interests and meet their needs, are in a unique position. These programs have the potential for and a history of engaging young people in experiences that can transform their lives in the most positive ways. In this article, the author explores the nature of engagement in what she refers to as "work" and some of the transformative experiences that can and do occur as a result of this "work." She also highlights and celebrates those programs that engage youngsters in developmentally appropriate transformative experiences. The article concludes that at a time when there is greater pressure to be more "school-like," after-school programs have a responsibility to think carefully about the developmental needs of the young people they serve and to meet these needs in creative and developmentally appropriate ways.