This paper introduces Daoist ideas on how to achieve social and psychological harmony and to bring about conflict resolution by analyzing some allegories from the Zhuangzi. The stories of the monkey trainer and Horsehead Humpback can be read as illustrations of a Daoist art of “walking two roads,” that both affirms and deflates right/wrong distinctions. While the two stories can serve as critiques of normative dogmatism and ideological trivialities, their function is by no means only negative. The dissolution of rigid right/wrong fixations has intellectual and existential therapeutic functions. It makes it possible to look at assertions of correctness or incorrectness in a broader perspective and to see them in larger contexts. It allows one to understand contingencies and perspectival limitations and thereby to think in more complex ways. The capacity to “be cool with” various points of view while at the same time not identifying with them is an important hermeneutic skill. It allows engagement with others through avoiding fruitless conflicts and eschewing the hardening of judgmental convictions. It opens up opportunities for conflict resolution beyond the realm of the normative.