In this paper, we investigate the working lives of three Australian teachers in the hardest-to-staff schools as they tell their stories of how teacher attrition has impacted them and others. Drawing on Zavelevsky & Shapira-Lishchinsky's ecological framework (2020) we analyse their work-stories to better understand issues impacting the teaching workforce in a time of extreme teaching shortages. Part of a larger study on teachers who remain in hard-to-staff schools, here we focus not only on the challenges facing the education workforce but also on the insights that may lead to better strategies to retain teachers in the schools that need them most.