Predictability tends to elicit a clear behavioral response and hence, for humans, it is a basic need in both their physical and social environment. However, the liberty inherent in a democratic society makes life essentially unpredictable and, in this sense, may create a sense of unease in its citizens who then may strive for stability in dogma. Dogmatism, however, is antithetical to democratic liberty. Once we take up this Janus focus of democracy, i.e., that it can lead to the best of times and the worst of times, it becomes clear that, to preserve democracy, we must educationally invest in anchoring predictability in the individuals rather than in the environment in which they subsist, and that we can achieve this (i) by explicating clearly to young citizens that the chaos of reasons doing battle is fundamentally different from the chaos of persons doing battle, and (ii) by shoring up what Charles Taylor (1989) calls strong evaluation, i.e., shoring up the ability to confidently and independently judge the worth of any proposed action and how it reflects on one’s ideal self. We will argue, perhaps counterintuitively, that this confidence in the predictability of one’s capacity for independent thought can best be achieved through an education that affords frequent engagement in “truth-seeking” interpersonal inquiries of the sort frequently utilized the practice of Philosophy for Children, but one that is buttressed by reinforcing the belief in Truth and, as well, by exposing participants to “truth-seeking” interpersonal dialogues that are focused on genuine, relevant, and difficult moral quandaries.