In this article the author considers how social media--a new, evolving, and increasingly pervasive form of communication and community--shapes students' attitudes towards practices of communication and community in their futures as political actors. How ought educators respond to this new world; can they lead their students into a culture of practice that seems, in many significant ways, alien to them? The author employs two potentially laudatory and critical frameworks, building upon the work of both John Stuart Mill and Hannah Arendt, to map the contours of a possible avenue of response to the aforementioned questions via the assertion that the essence of those social media sites and services--paired with their corresponding method(s) of engagement--may be well understood as rooted in a novel culture of sharing. Investigating this push to share allows educators to consider their practice in the face of a new feature of their world, finding themselves and their students in a moment of uncertainty which challenges and reinforces one of the central aims of their common project: the preparation and shaping of future political actors.