This qualitative journey explores how literature informs and challenges my under¬standing of teaching and learning. Insights, questions, and conflicts are revealed through a series of essays in which my evolving teacher identity is illuminated through literature and imagination. Hopefully reading this portrayal of literature, which has been a source of educational insight and imagination for me, will be of use to other educators as they reflect on their own teaching. The primary works of literature used to facilitate this journey are: The Red Badge of Courage (1895), Les Miserables (1862), and American Idiot (2004); Light in August (1932), Seinfeld scripts (1991-98), and Frankenstein (1818); and The Odyssey, Night (1960), and The Souls of Black Folk (1903). By delving beneath my exterior ‘teacher mask,’ a collage of images, anecdotes, reflections, aspirations, and fears is exposed. As a resource for pre-service teachers or a reflective exercise for veteran teachers, this study aims to benefit educators by providing a new pathway through which to better understand their intrinsic identities as teachers. Each chapter concludes with “Recommendations for Reflection” that readers are encouraged to consider individu¬ally and/or collectively. The spirit of daydreams allows me to integrate literature, autobiography, and imagi¬nation through inventive and inspired discourses with literary figures, using au¬thentic quotations as content for original commentaries that further examine the intrinsic nature of teacher identity. My hope is that this journey will inspire other educators to further reflect on realities and possibilities of what it means to be a teacher.