Moving beyond current discourses of increasing self-confidence, reduction of social anxiety, disengagement, and risky behaviour as positive outcomes of participation in youth theatre training, this article identifies volunteerism, entrepreneurship, and generativity as beneficial outcomes to youth participation in the Loose Moose Theatre Company (LMTC) community in Calgary, Alberta. This article also discusses the increased benefits of learning that occur as compensation for time spent volunteering versus learning in exchange for a monetary fee. Examples of successful and notable LMTC alumni are included.