The purpose of this study was to explore how practicing music teachers find meaning through musicking outside of school. Musicking, used as a verb, encompasses all musical activity both formal and informal across a range of engagements. In this multiple case study, the reflections, perspectives, and experiences of a group of practicing music teachers were investigated. Cross-case analysis was conducted to find how time has shaped prior experiences and the desire for future musicking opportunities. Findings suggested that music teachers must navigate a complex web of identities in early career assignments as the realities of life often conflict with the desire to continue musicking. Implications were drawn on the importance of dual musician-teacher identity development in teacher education models and post-graduation professional development opportunities.