Recent scholarship on Thoreau’s thought has pushed in two opposing directions: some have maintained that Thoreau’s withdrawals from political engagement were actually intended to serve democratic ends, whereas others have argued that Thoreau’s political engagement was a lapse in his better judgment. In this essay, I contend that neither interpretation of Thoreau’s thought fully captures the roles that political engagement and disengagement played in his life as a dissident. Instead, via an examination of Thoreau’s “Walking” and his reform papers, I argue that Thoreau modeled a dialectical approach to dissent, where the “antithesis” of withdrawal served as a specific antidote to the personal toll of the “thesis” of political action. As I show, Thoreau’s attention to the potential costs of radical dissent makes his dialectical model especially relevant for those for whom the costs are highest, including contemporary women activists of color. For these women, normalizing a practice of continual disengagement from activism might benefit them in ways that collaborative solidarity cannot.