In this conversation, Michael A. Peters discusses his philosophy of education in and for the age of digital media. The first part of the conversation classifies Michael Peters’ work in three interlocked themes: philosophy, political knowledge economy, and academic publishing. It explores the power of dialogue for philosophical inquiry, positions dialogue in relation to human learning, and analyses the philosophical thesis of postdisciplinarity. It assesses the role of “big data” and “learning analytics” in (educational) research, and links various approaches to inquiry with creativity. The second part of the conversation introduces the notion of “philosophy as pedagogy,” and introduces Michael Peters’ philosophy of technology. It inquires the role of educational philosophy in the contemporary network society, and explores links between postmodernism / poststructuralism and (neo)Marxism. The third part of the conversation explores the relationships between universalism and the Internet, locates digital postcolonialism, and looks into legacy of the Frankfurt School for learning in the age of digital media. Finally, it discusses Michael Peters’ lifelong fascination with Ludwig Wittgenstein, and outlines the main trajectories of Wittgenstein’s work into present and future of educational philosophy.