This chapter revisits a previous account of collaborative self-study and teachers’ work (Kenny et al., 2016) as the impetus for reflecting on the authors’ current research with two colleagues about 42 Australian teachers. The research project investigates the teachers’ emotional experiences in their working lives, against the backdrop of national and international influences on teachers’ identities. The authors engage in collaborative self-study to articulate and analyse their interpretations of the study participants’ experiences, in order to explicate their separate and shared responses to a pair of co-developed fundamental questions about education, including a focus on the wider forces framing contemporary learning and teaching, the transformative power of learning and teaching, and the costs and risks attending current teachers’ work.