The potential of digital technologies has brought new and exciting challenges for educational institutions and their teachers. One of the main challenges is related to the need to design new learning scenarios using the tools available on the social web. The focus is both on a new student model and on the new needs of the labor markets, which today seek, in their employees, skills that go beyond the foundational ones and that promote higher-order behaviors, assuming that it is increasingly necessary to adopt new strategies and new methodologies that promote pedagogical practices of emancipation, namely with a view to developing skills for the 21st century.