Autonomy operates as a key term in debates about the rights of families to choose distinct approaches to education. Yet, what autonomy means is often complicated by the actual circumstances and contexts of schools, families, and children. In this essay, Terri S. Wilson and Matthew A. Ryg focus on the challenges involved in translating an ideal of educational autonomy into the "nonideal" contexts and circumstances that surround families' choices. Drawing on the methodological insights of Elizabeth Anderson and John Dewey, they sketch out a nonideal approach for exploring autonomy. Wilson and Ryg particularly focus on Dewey's notion of an ideal, his treatment of autonomy as a concept, and his view of the self. Such a nonideal approach draws attention toward the specific circumstances, habits, and environments that make autonomy possible. Wilson and Ryg illustrate the salience of this nonideal approach by exploring one example of an empirically engaged study of autonomy.