The following essay explores aspects of my professional identity as a teacher of English, presenting a focus on “the reflexive project of the self” (Goodson, 1998). I argue for the way rich professional learning can occur by keying into a discourse that values penetrating reflection on classroom practice, teacher identity, self and professional knowledge, particularly in the wake of current professional challenges about professional learning. This paper aims to foreground a space that was, for a time, difficult and invested with uncertainty. Yet, the opportunity to experience a textually rich moment of professional growth arose from dilemmas and “chaos” (Parr, 2004, p. 41) as I grappled with a socio-cultural context different from what I had previously known. The other key focus of the following essay concerns the way my new context, teaching in an all-girls, Jewish independent school in Melbourne, prompted me to reconsider the nature of schools as interpretive communities. As a teacher of literature my aim is to open up texts to a diverse range of readings, enabling my students to explore the complexities of language and meaning. This approach to the teaching of reading is not one promoted by statewide examinations which tend to reduce texts to the one (examinable) meaning. Nor is the idea of promoting a multiplicity of interpretations necessarily associated with religious orthodoxy. I show how I was able to use the cultural and religious understandings of my students to open up alternative readings of literary texts in a way that is congruent with post-structuralist understandings of language and meaning.