Investigations pertaining to career trajectories and vocational identities of professional classical Australian singers are uncharted and lack specific empirical evidence. Rarely do studies explain the professional singers' experiences and the processes they undertook to reach goals, to comprehend their deep identification with the craft, and acknowledge the specific market conditions which drive their career. This research investigated the careers of Australian classical singers through a qualitative interview-based study and analysis, which outlines the trajectory of the professional singers' careers as these became evident through their experiences. Extensive interviews were conducted with 13 retired professional singers' and the subsequent thematic analysis found a trajectory of development and decline. Major career theories and empirical studies from elite dance and sportsperson were interrogated. An analysis of the singers' experiences of their professional life was undertaken, and implications arising were related to career models from the film industry to discourses from cultural economics and sociology, to music training concepts and entrepreneurial approaches to working in the creative arts. The result was the identification of a distinct career typology comprising several stages: (1) "pre career;" (2) "breaking in;" (3) "peak stage;" (4) "denouement;" and (5) "moving on." The study found there is a critical link between pre- and post-career stages that has implications for training. Other findings include that creativity and identity are tightly intertwined for the professional singers in the study, and when seeking new directions following the denouement stage, the majority of the singers attempted to remain attached to an artistic field. The findings suggest that training for artists' in career planning, pedagogical practices, entrepreneurship and attention to issues of wellbeing have often been inadequate in this industry and it is only in the consideration of the lifecycle of a creative performance career that the critical link between pre- and post-career stages can be made.