In this study, occupational life histories of Montessori teachers in Sweden have been constructed in collaboration with a group of them. Data exploration and analysis have included journals, interviews, written reflections and conversations. Of interest has been to shed light on underlying values, ways in which professional roles reflect personal values and teachers' reflections on the present and future perspectives of Montessori education. Life histories make it possible for each individual teacher to be presented in the light of his/her own personal attributes and unique qualities as well as in relation to a wider (historical, cultural) context. The overall aim has been to come to a better understanding of what it means to be a Montessori teacher, by getting a group of Montessori teachers to reflect on their lives and work. Valuable insights have been gained concerning the changing roles of teachers in contemporary educational settings.