Three decades into the ‘digital age’, it is clear that the promises of the digital ‘revolution’ in education and elsewhere are still unfulfilled. Furthermore, the changes associated with digitalization generates new and unexpected challenges. With this collection, we seek to map these challenges and to offer professional educators some conceptual tools to address them. Inspired by S. Freud’s analysis of ‘civilization and its discontents’, this collection of essays originates from an effort to problematize the impact and the future of digital technology in education. The essays in this collection offer the reader a holistic approach to the challenges of the digital turn in education. The core idea is that education is itself influential on the social construction of that part of reality we call the ‘future’: the horizon of possibilities that inspire and gives us direction when the present is troubling.