Over recent years Singapore has developed a strong adult and vocational education system based on those of Great Britain, Australia and New Zealand. Its Continuing Education and Training (CET) sector makes use of competency-based training in the form of Workforce Skills Qualifications (WSQs) which are delivered in mainly small private providers by learning facilitators qualified through a range of WSQ-based training programs. Most facilitators are mature-age and second-career people drawn from diverse career backgrounds and employed on a casual and part-time rather than ongoing basis. They identify themselves as "freelancers" in the training market place and compete vigorously for the work opportunities available. In the paper we argue that continued workplace success is premised on a strong sense of professional identity and its management through a process of "shapeshifting" according to the diverse requirements of the adult education industry. We explore this idea through revisiting three of our projects examining Singaporean CET educators and ask of our data a new question: "How do individuals 'become' and 'be' Singaporean adult education freelancers?" We draw our insights from interviews with freelancers, Singapore's political and economic context and a range of literature drawn principally from a socio-cultural theoretical perspective.