Critically reflexive practice is at the heart of counselling, and even more so when clients come face to face with (im)possible choices. As counsellor educators, the authors show counselling practice at the edge of uncertainty. This article features a counselling context in a secondary school. It describes a fictional situation where action is called for in the midst of undecidability, at an impasse in the life of a young woman client. The article explores the aporia that confront the young woman and the counsellor, in the context of education, career, families, cultures and communities. The authors show that these explorations produced transformational questions for their teaching practice as counsellor educators.