In this paper, I discuss the connection between happiness and reason in the work of Herder, Kant, and Hegel. First, I consider Herder’s integration of satisfaction and rationality and Kant’s complete separation of rational imperatives from particular experience. I discuss (and partially endorse) Kant’s critique of Herder as arbitrary and overly reliant on analogy. I then turn to Hegel’s response to this debate. I argue that Hegel’s Phenomenology provides an integration of happiness (in the broad, Aristotelian sense) and reason that is not subject to the same pitfalls as Herder’s solution. I examine two examples of rational critique in the Phenomenology and conclude with brief remarks about happiness and the rational society in Hegel’s work.