This essay takes a look over Walter Benjamin’s life and work. It’s focused on five of his writings: The Work of Art in the Age of Mechanical Reproduction, On Some Motifs on Baudelaire, Experience and Poverty, The Storyteller, and the introductory chapter of The Origin of German Tragic Drama. These texts allow an analytic approach to both human and art’s experiences, under the eye of the technical reproducibility. This analysis allows us to think about new ways to approach the education field, new forms of subjectivity, especially those brought by the new mass media of communication.