The purpose of this study was to examine the development of "21st Century Competencies" (21CC) through the secondary school band programme. The researcher used ethnographic research methods to document the lived musical experiences of students from a high performing secondary school band in Singapore, captured the voices of the participants through extensive focus group discussions and informal interviews, coded and analysed the data using the Singapore Ministry of Education's (MOE) 21CC framework. Findings provide empirical support for the MOE's initiatives to developing 21CC through music and the arts. Three interrelated themes--performance, peers, and patience--emerged as specific enablers of the school band to nurture 21CC. These enablers, however, may paradoxically be impediments for the development of 21CC; an awareness of how these enablers may sometimes be hindrances is necessary to optimize twenty-first century learning through the arts.