Recruiting and retaining vocational education and training (VET) educators is an increasing challenge in countries across the world. So understanding their transition and retention is vital to the development of a sustainable workforce. This paper draws on interviews with senior administrators of Australian training providers and survey data from practising VET teachers and trainers to identify factors that most influenced these educators to remain in what was, for most of them, a second or later career. The research found that the major influences on retention of new educators in VET were partly extrinsic, including employment conditions, lifestyle balance and support for professional development, and partly intrinsic, including a supportive culture and job satisfaction through enjoyment of teaching and giving back to industry. The findings provide training providers with a clear indication of what encourages educators to make a long-term commitment to VET teaching and what motivates them to perform at their best once they have made the transition.