There is no doubt that as technology continues to change, the generation of students will change also. The best preparation, then, is to train one's own mind to think digitally so that one can best create policies, programs, and interactions that enable a student to connect the two worlds in ways that are productive, satisfying, and meaningful. This article discusses five key norms of the digital culture that may explain how students think about technology and how one can help them manage it. These include: (1) Internet use as play; (2) virtual identity as fictionalized personas; (3) virtual socialization as a complement to live community; (4) the global town square; and (5) online community as a response to barriers to live interactions.