In this study, I explore some of the inherent and lived tensions or paradoxes produced through the principles and practices of the governmental and educational contexts of the neoliberal milieu, through the lens of a contemporary countercultural movement. In the particularities of this movement, a community of practice known to insiders as the “unschooling movement,” families seek to challenge the rationalization and standardization that they perceive as rampant and objectionable in state-overseen education. This is an ethnographic study of the countercultural praxis and identities entailed in cultivating unschooled children through distinctive childhood, familial, and community-based experiences. I consider dimensions of lifestyle that include attachment parenting, the organization of space and time, consumption, community-based education and legitimation (portfolio evaluations) to prove educational equivalence. This study reveals the hidden resources of social capital and educational capital used to sustain a countercultural educational alternative.