To be a writer, one must write. Research shows when teachers write and identify as writers, they transfer their writing practice into their classroom, positively impacting their students' writing development. Shifting instructional practices or identities requires educators to self-determine a gap in order to take on transformative learning experiences, such as mentoring, professional development, or modeled learning. Often professional development is chosen by administrators for educators to shift their instructional practice, ignoring a teacher's curriculum-maker role, and best-loved self identity. This narrative inquiry analysis details one teacher-writer in a creative writing professional development residency as she supports educators with a goal to transform educators into teacher-writers. This chapter includes the small step successes and systematic struggles the author faced as she modeled the writer's craft and writer's workshop strategies with her teachers. The chapter concludes with a discussion on the important role teachers have to decide, navigate, and discover their own best-loved self-teaching identity.