Adult learners who write their life story embark on a process of personal self-reflection and meaning making. Some of their narratives center and remain on the detailing of life events. Other writing goes further, associating feelings and emotions that lead to additional exploration and reflection. Other writing goes still further, uncovering experiences and emotional states, previously unspoken, perhaps even incomprehensible. Each has its benefit for the writer and for the reader, but it appears that when writers move into the reflective mode, and even further into exploring the “uncanny” aspects of their life, the major benefits of autobiographical writing surface as a profound, even transformative, learning experience. In this article, the author examines selected autobiographies written by adult learners in adult and higher education studies and considers the significance of each of these “tellings” in promoting student growth and development.