Creative industries are key drivers of modern economies; however, analysis has traditionally advanced a market-failure model of arts and culture (Potts, 2012). A negative socio-economic paradigm can have an adverse effect on post-secondary school students' career choices and continued engagement in the arts. This article reports on the findings from the first stage of a longitudinal study that tracks the life trajectories of a group of young people who at some time in their school years were winners and finalists in a university funded art prize. The participants, now in the early stages of their tertiary studies and careers, were surveyed in order to learn whether they had continued to engage in visual arts practice, continued on to further training in the arts or work in creative occupations. Participants in this study offered insights into their motivations to pursue arts-based careers as well as their understanding of the challenges that face those who desire a career in the Arts.