It is hardly a novel claim that the work of Ursula K. Le Guin (1929–2018) contains influences from philosophical Daoism, but I argue that this influence has yet to be fully understood. Several scholars criticize Le Guin for misrepresenting Daoist ideas as they appear in ancient Chinese philosophical texts, particularly the Dao De Jing and the Zhuangzi. While I have sympathy for this charge, especially as it relates to Le Guin’s translation of the Dao De Jing, I argue that it fails to understand the extent to which her fiction contains her own philosophical development of Daoist ideas. Looking at some of her most influential works (e.g., The Left Hand of Darkness, The Dispossessed, The Lathe of Heaven, A Wizard of Earthsea, etc.), I suggest that Le Guin’s fiction is better seen as a refocusing of Daoist concepts such as complementary contrasts and non-action (wu wei) in the contexts of modern feminism, modern anarchism, science fiction, and fantasy. Le Guin was not trying to represent ancient Daoism as a scholar. Rather, she was trying to reimagine Daoism as a creative artist and philosopher in her own right. This way of viewing Le Guin’s work does not fully exorcise the specter of the possibility of Orientalist cultural appropriation, but it does make the issue more complex in a way that can deepen further conversations. To what extent can an artist be guilty of misrepresentation if representation was not, strictly speaking, her goal? I end with a brief reflection on what is perhaps the deepest philosophical lesson of Le Guin’s work: everything is more complicated than it first appears. On that note, the present article is an attempt not just to do philosophy about Le Guin, but to do philosophy in a Le Guinian fashion, which requires rethinking the metaphor of combat that guides much academic philosophy today.