This paper introduces the complex relationship among technology-school-society as framework of the discourses, processes and policies of the daily practices of schooling. Nowadays, we live in an interconnected digital ecosystem that represents a powerful architecture for user participation, posing new challenges to education system. Particularly, youth participation in this networked world suggests new ways of thinking about the role of education. The focus is not on the technology as such, but on the innovative dynamics it can result in. At the base of the information revolution are new ways of relating to one another, new forms of discourse, of the creative and collaborative problem solving, new ways of interacting, new kinds of groups, and new ways of sharing, trading, and collaborating. “Participatory culture” is emerging as the culture that absorbs and responds to the explosion of new media technologies. It highlights the cultural component embedded in the new technologies practices. Openness, social networking, “connective intelligence”, making, digital fabrication are especially promising in this regard as a part of the digital culture. What is fundamental are the ways in which they empower us to rethink the cultural design of the new learning environment.