Ongoing efforts to integrate structuralist semiotics (following Saussure) and pragmatist semiotics (following Peirce) should return to earlier Eastern sources where the two are already integrated – or, more acturately, never separate to begin with. Building on Pelkey (2021), and the newly emerging semiotics of Jingshen (Zhang & Yu 2020; Zhang & Yao 2022), this paper returns to second chapter of The Zhuangzi with this hypothesis in play, to identify ways in which the argument of the text relies of a robust mixture of what we might now identify as structuralist and pragmatist insights. Using the macro-structure of the text for interpretive leverage, the argument hinges on aesthetic and transformational relationships between the central and peripheral rings of the Qiwulun. What emerges is an original pre-unification of structuralism and pragmatism rather than their reunification, but the challenge that acceptance of this pre-unification faces in Western academia are in need of special attention since they go beyond the received aims of scholarly inquiry, which have come to be associated with control, certainty, and predictability instead of “holistic flux of mind, vitality, and creativity” (Zhang & Yu 2020) and “the release of meaning” (Zhang & Yao 2022). Considering the deeper purposes of semiotics and academia (even in the Western world), and the ultimate aims of both structuralist and pragmatist approaches, I argue that Zhuangzi’s semiotic vision is intent on meaningful integration with the world, involving elements of diagrammatic modeling, bodily meaning construal, textual criticism, and narrative play in the service of transpersonal therapy.