Despite scholarly interest in the disruptive changes to have affected media industries, and a growing understanding of how Creative Industries now operate as labour markets, to date there has been little consideration of the way in which media careers are navigated over the longer-term. This article focuses on the subjective experience of media work over time. We report on a study of a single cohort of Media Production graduates of a UK university, who are now in mid-career. They reflect on: their transition from University into work; freelancing; job satisfaction; industry changes; and work-life balance. In our analysis we note the way in which the demands of media work are experienced through the prism of age, and life stage. Contrary to our presumption that the most significant challenges are experienced in early career, our findings suggest that media careers may become increasingly difficult to sustain over time, and are characterised by a limited 'shelf life': the rate of attrition from media work by mid-career is particularly striking. We suggest that this underreported feature of media work is likely to be systemic and to have wider implications.