This chapter explores how worldschoolers cope with loneliness, homesickness, and unrootedness on the road by creating new kinds of community. As the children, especially teenagers, crave connection with their peers, parents reconcile their competing desires for individual freedom and a sense of belonging by seeking out what worldschoolers call a “tribe of rebels.” In contrast to the isolating effects of the “new individualism” that pervades late modern society, worldschoolers establish a “new togetherness” in communities that are mobile and mediated, temporary and intermittent, intentional, curated, and commodified. The chapter argues that even though these communities provide a source of communal belonging, they are essentially a lifestyle choice whose primary purpose is to support worldschoolers in their individualized pursuit of freedom. The “come-and-go” sociality that worldschoolers demonstrate in these communities also offers some insight into the kinds of social skills their children are learning, things like collaborating in diverse and temporary teams, maintaining nomadic friendships, and sustaining social relations through mediated channels. These are the kinds of competencies children will need to navigate their social and professional lives in a mobile future.