This is a personal account of the author's naivete, growth, and hope as a literacy educator after she left her position as a university professor to teach reading to young adolescents. She describes how her experience and academic expertise did not fully prepare her for the realities of working in a middle school and how she became more aware of the need to improve adolescent literacy instruction and more sensitive to adolescents with reading and writing difficulties. By describing the literacy life of one adolescent, the author illustrates inadequate assessment and learning conditions and her frustrations and concerns with our current educational system. She concludes with concrete recommendations that can be implemented in a comprehensive literacy program.