This paper aims to investigate how “unconscious rebelliousness” of young musicians can be the key to cultivating innovation in the next generation. Unlike other Classical music programs, Face the Music, is a dynamic youth program in New York City dedicated to studying and performing works by living composers, including its own members. Students participate in improvisation, jazz, composition, music technology, and the use of new technology like virtual reality. Through an in-depth case study and conducting focus groups of the youth participants and their mentors, this study focuses on revealing the identities of the young musicians. Identity is more than just self-identification (O’Brien; 1995); it changes and transforms and it is not a singular unit (Burke, 2006). It is revealed that “unconscious rebelliousness” motivates the participants to develop their polytonal roles. They become so much more than the typical instrumentalists. In addition, the young musicians at Face the Music do not define themselves as one singular self. Implications of this study include the need for more future music programs to be re-conceptualized in order for young musicians to experiment with different techniques and innovative tools and to embrace the hybridization between the traditional instrumental education with the contemporary performance practices.