This article focuses on ways in which teachers’ conceptions of their professional roles reflect their own personal values, beliefs and convictions. Data exploration has comprised journals, interviews, written reflections and collaborative contextual analysis. Analysis of the teachers’ occupational life histories and the findings as a whole have been used to shed light on underlying values, conceptions of professional roles and future perspectives. Eight Swedish Montessori primary school teachers participated in the study. Although relevant issues pertaining to the group as a whole will be raised here, this article will focus mainly on one teacher. By presenting Nora’s story I hope to be able to illustrate, through a personal portrayal, the complexities involved in coming to terms with personal values and professional roles.