Nineteenth-century American political thinkers like Emerson, Thoreau, and Whitman advocated for and sought to exemplify a life of self-direction and critical self-reflection, or personal autonomy, as a means of contesting entrenched routines of democratic-capitalist normalization and as a way of resisting a host of institutional disciplinary pressures. Today, the ideal of personal autonomy within a diverse liberal society is branded by many as a form of "comprehensive" disciplinary normalization in its own right. In this essay I offer a reconsideration of this reversal in the appraisal of the value of autonomy within pluralistic democratic societies and argue that the abandonment of autonomy is a symptom of a mistaken understanding of the personal-ethical qualities upon which a democratic culture depends and a maladaptive concession to neoliberal norms. To confront these challenges, I draw upon a range of Emerson’s writings to offer some ideas about how a reconstructed ideal of aspirational autonomy might inform contemporary politics without unduly constraining moral pluralism or undermining toleration.