This article examines the career opportunities, challenges and trajectories of creative work. As part of the Creative Trident approach to creative workforce measurements, the embedded mode draws attention to creative work as it is undertaken outside of the creative industries. This article further considers and conceptualises the complex careers pathways of creative workers. Firstly, creative workers in non-creative occupations in other industries are discussed to highlight the challenges and barriers to securing creative employment and the balance creative workers establish with other forms of employment. Secondly, students from creative courses going into non-creative occupations in other industries is discussed to highlight challenges students face in making the transition from higher education to creative employment in terms of workforce expectations and the competition amongst graduates. This article critically evaluates assumptions about transitions from education into creative work employment and associated career trajectories.