This paper is in the form of a short narrative trail through my developing ideas about identity and my increasing understanding of the power of discourse and language in constructing what we take to be real. It is part of a larger study which began with a curiosity about how young people in ‘late adolescence’ construct their identities (O’ Grady, 2012). I draw on some of that work in this article to provide a rationale for the need to develop a politicized practice of guidance counselling. A creative approach to research and counselling encourages the expression of multiple truths exposing knowledge as socially constructed (Eisner, 1988) and therefore open to reconstruction. In this way the approach is both playful and political. The second part of the paper attempts to offer some assistance in applying a critical psychology that is artful and politicized to the practice of guidance counselling.