Australian secondary education has endured a chronic shortage of qualified mathematics and science teachers for a number of years, particularly in rural and remote areas. A longitudinal research project examining the capacity for the holders of PhD level qualifications in mathematics and science to be utilised as one means of addressing this shortage has been commenced at two regional Australian universities. This paper reports on the pilot study which utilised semi-structured interviews involving five participants at various stages of the transition into secondary school teaching. The interviews examined the motivations of the participants to enter secondary teaching and the challenges associated with the transition. The principle findings were that all but one of the participants had considered secondary teaching as a career option for an extended period that, for some, had predated their PhD study. Those participants who had engaged in postdoctoral study reported substantial professional identity challenges associated with the change in career. Financial security considerations figured strongly in the decisions to initiate the transition to secondary teaching. The opportunities for further research identified by the pilot study are discussed.