The experience of precarious employment is growing across the occupational spectrum and some scholars have predicted that there will be a corresponding rise in anger, anomie, anxiety and alienation amongst those affected. Exploring more intimately how precarity might be differently experienced and confronted, this paper bases itself on a dialogue between "Bethan", an underemployed youth looking for full-time employment and me, a university-sponsored academic advisor in a disadvantaged suburb in Sydney approaching the end of my fixed-term contract. From our very different positions, we reflect on our respective experiences of the employment market; the promises of formal education; and against the backdrop of the present reality, our feelings about the future. Drawing on the work of Erich Fromm and Bethan's approach to life hitherto, this paper also offers a reconsideration of what it means to be "productive" in the face of unemployment and uncertainty.