Informal mentoring relationships develop out of mutual identification and the fulfillment of career needs. As new faculty, we struggled to balance and decipher all the various facets inherent in the research, service, and teaching responsibilities in our new roles. This paper chronicles an informal comentorship collaboration we struck up to support our efforts as second-career academics in the field of education, seeking to navigate our way through institutional resocialization at a mid-sized Canadian university. Using a collaborative autoethnographic approach, we collected data comprising handwritten notes, tape-recorded coversations, e-mail reflections, and metareflections crafted after scheduled meetings over the course of a single academic school year. We sought to link theory with practice while using our own stories, narratives, and lived experiences as a basis for understanding our respective journeys toward social health and well-being in the academy, as well as our proficiency and competence as new scholars. From our analysis, we were able to interpret more clearly our roles, responsibilities, and needs, as well as institutional and departmental culture and norms. We offer practical implications and five lessons we have learned regarding the use of informal comentorships as an approach to managing the institutional resocialization of second-career academics.