The author taught a course titled ‘Autobiography and History’ in East Harlem in 1996, aiming to help students understand how historical times help shape the lives of people. Using the modes of inquiry and narratives, students were required to revisit and expand their own experiences and place them within historical context. The chapter examines how students from lower socio-economic groups are affected when disciplinary knowledge is taught. The author proposes that enhancing students’ understanding of themselves requires a re-conceptualization of history where historical events such as the Industrial Revolution become flexible frameworks where students can test widely held beliefs or examine social inequalities. The author believes that it is required for students like hers in East Harlem to have this opportunity at school since it is usually their sole opportunity to explore the world through history, science or literature. The author continues the chapter with an examination of the course which attempted to bridge the personal stories of students with historical events and place them in context. It was important for students to think like historians by understanding historical points of view, analyzing continuity and change over time and having multi-causal explanations of a historical event. The author continues with a description of the three units of the course: understanding and making narrative, revisiting of American history of the 1960s and 70s as a contrast to the 1980s and 90s, and the conservative turn of the 1980s and 90s. The author continues with a discussion of the challenges students faced and how they engaged in disciplinary thinking. Expanding upon three struggles students faced, the author offers three detailed student examples. She concludes by stating that it is important to refocus attention in the substantive aspects of education.