School leadership is a fast-paced job where stakeholder feedback is frequent, and decision-making requires quick thinking and strong organization. When school leaders transition from practitioner to scholar, they face a dramatic change in pace and responsibility. Unlike their peers who come from academia, practitioner-scholars experience a unique context and career shift that requires navigating unfamiliar organizational structures and translating existing skills into new contexts. This collaborative autoethnography explores the lived experiences of two junior faculty who recently transitioned from the campus principalship to the tenure track professoriate during the COVID-19 pandemic. Through a process of individual writing, group reflection, and shared analysis, common themes emerged from the data, including expectations, relationships, and identity. The research discusses processing unfamiliar experiences in academia, negotiating the re-identification of self, and developing new attachments during the shift from doing the work to supporting and advancing the field.