This article presents a heuristic research project designed to explore the role of personal writing in the development of the self. True to the heuristic process as outlined by Moustakas, the author analyzed over 30 years of personal poetry and journal writing through her mother’s mental illness and brother’s traumatic brain injury and epilepsy. Phase two of the project included nine participants (co-researchers) who were lifetime writers. Results indicated themes related to the (i) interpersonal and personal nature of writing, (ii) the spiritually transcendent nature of writing, (iii) the fact that writing facilitates perspective taking, (iv) the importance of challenge in personal growth, (v) the dynamic nature of writing, and (vi) the power of writing to influence personal identity. The paper presents the process, stories of the author and three participants, synthesized results, the power of the heuristic process, and potential application to the creative arts.