The classical music academy is a site dominated by traditional meanings of creative practice and an image of the professional creative career as solo performer that is fully available to only a very few students after graduating. The purpose of the study reported in this paper is to explore career-young professional pianists’ talk about the transition from study within a music academy to working life. The focus is on the ways in which they characterize the nature and significance of this transition from very traditional practice and study, and how they (re)negotiate their identities as professional musicians and pianists in contemporary working life. Four classical pianists were interviewed in-depth about their musicianship, including their transition from study to working life. The qualitative analyses presented here suggest that, as they talked about their transitions and developing musicianship, the speakers constructed, re-constructed and oriented to notions of professional trajectories. Such trajectories are emergent, relational and contextually constituted (Sawyer 2003; MacDonald and Miell 2002; Moran and John-Steiner 2004). Rather than being fixed or dependent on communal expectations, they reflect creative freedom and independence, encompassing multiple influences. Crucially, the transition from study to working life is implicated in the process of assuming agency in respect of one’s own musicianship and career—a process that involves identity work, the (re)negotiation of pathways, narrations and trajectories.