Some contend that politics functions best when deference is given to tradition and authoritative community norms, while others argue for the importance of independent thought and doubt about received sources of authority. Insight into this question can be found in the work of Alexis de Tocqueville. While Tocqueville is often taken to regard the doubt characteristic of intellectual independence solely as a pathology, I show that he also saw it as a potential precursor to conversation, a stimulus to self-assured conviction, and a counter to distortionary abstractions. Nonetheless, Tocqueville also elaborates the destructive outcomes of too much doubt and intellectual independence. I identify the ways in which he seeks to discipline and educate the drive to independent thought so as to attain its benefits without falling victim to its pathologies. In doing so, I demonstrate the ways in which Tocqueville can be a guide to navigating the perennial tension between intellectual inquiry and authoritative community norms.