Unlike the work available in many creative disciplines, musicians and dancers have the possibility of company-based employment; however, participants outweigh the number of positions. As a result, many graduates become “enforced entrepreneurs” as they shape their work to meet personal and professional needs. The similarities between initial music and dance careers offer opportunities for research across both. This article explores the career projections of 58 music and dance students who were surveyed in their first week of post-secondary study. It contrasts these findings with the reality of graduate careers as reported by five of that cohort four years later. In contrast with the students’ focus on performance roles, the graduate cohort reported a prevalence of portfolio careers incorporating both creative and non-creative roles. The paper characterizes the notion of a performing arts “career” as a messy concept fraught with misunderstanding. Implications include the need to heighten students’ career awareness and position intrinsic satisfaction as a valued career concept.