Traditional career theories are largely situated in organisations, where career trajectory is mostly an upward movement, usually associated with greater managerial responsibility and corresponding salary and benefits increase. With increasing growth in the creative economy and creative class, this article examines the complexity of creative work patterns and the associated skills required for sustainable musical careers. A longitudinal qualitative case-study approach documents the careers of eight professional musicians. Interviewees narrated their last decade through semi-structured interviews, which were analysed using thematic analysis. Findings suggest that musical careers are multifaceted and tend to have a lifespan effect. To remain sustainable, a baseline of well- maintained technical skills and musical expertise was a given, but a myriad of soft organisational skills was key.