Sailing in a Concrete Boat: A Teacher’s Journey is a novel-length narrative composed in a sequence of short fictions and poetry linked by recurring characters, themes, events, and setting. The narrative explores the experiences and emotions of a school teacher named Caleb Robinson. He teaches in a conservative church-administered school in a rural Newfoundland town called Morrow’s Cove. Caleb struggles to understand what it means to be a teacher, husband, lover, friend, father, Christian, and human being. Sailing in a Concrete Boat raises many questions about pedagogy as questioning, freedom of expression, conservative religious beliefs, breaking silences, and curriculum as cultural reproduction instead of cultural transformation. Above all, Sailing in a Concrete Boat seeks to narrate the complex lived experiences of a school teacher as he questions love, family, community, vocation, well-being, romance, spirituality, authority, silence, truth, and identity. In order to make sense of his tangled living experiences, Caleb is always remembering and researching his past in order to write and rewrite his future. Sailing in a Concrete Boat will be a valuable resource in both undergraduate and graduate courses in teacher education, curriculum and pedagogy, life writing, poetic inquiry, arts-based research, and narrative inquiry.