Objective: The purpose of this paper is to share the results of research into the experience of teacher risk-taking in the classroom. The development of children as risk-takers is featured prominently in curriculum documents and reports calling for the competencies of 21st century learning. Teachers are expected to become 21st century learners who model risk-taking. The repeated calls for the development of risk-taking students through the modelling of risk-taking teachers makes the experience of risk an important pedagogical question. However, 21st century learning documents do not take up substantively the meaning of teacher risk-taking.Research Design: Phenomenological research is concerned with the unique and the individual and in that regards each teacher-participant represents particular perceptions of risk-taking experiences and responses to risk in the classroom. The six (6) teacher-participants responded to a call distributed widely to teaching staff in a Canadian school district. The inquiry relied on phenomenological interviews and experiential life world material. In this paper three phenomenological themes are described: risk and readiness; risk and the in-between spaces of pedagogy, and risk as exploration and finding a way. This research allows us to understand teachers' lived experience rather than assume the meaning of the terms risk and risk-taking.