The present chapter is a systematic exploration of “Daoist contemplative psychology” as old/new paradigm. It discusses Daoist contemplative psychology as such; the informing praxis-based view and approach; and the associated contemplative practice. It concludes with a lived/living Daoist perspective on the relevance and applicability of these materials to a possible “anti-therapeutic” or “non-therapeutic” approach to human being. While the Abyss often invokes danger and fear, especially as encountered beyond the known/knowable, it actually represents freedom and possibility. It is a vast expanse without set boundaries or limitations. The present chapter in turn continues my research on “Daoist contemplative psychology,” which refers to psychological views informed by and informing Daoist contemplative practice and contemplative experience. I begin with a critique of therapeutic meditation as a form of “capitalist meditation,” in which I suggest other contemplative trajectories that prepare the way for a more revolutionary tradition-based and decolonial psychology. Drawing upon the Dutch psychologist Han de Wit’s Contemplative Psychology (1991), I then discuss “contemplative psychology” and its applicability to the inner cultivation lineages of classical Daoism, the earliest Daoist religious community that emerged and developed from the fourth to second centuries BCE. This is followed by exploration of the root in Daoist apophatic and quietistic (emptiness-/stillness-based) meditation. Such is theory informing practice, and practice informing theory. The article concludes with a lived/living Daoist perspective, rooted in the critical subjectivity of a scholar-practitioner approach (SPA) and critical adherent discourse (CAD), on the relevance and applicability of the old/new paradigm of Daoist contemplative psychology, including the associated vision of human possibility and spiritual realization. Here I also challenge and offer alternatives to the current constructions of “meditation as medicine” and “meditation as therapy.” Daoist practice-realization is fundamentally atherapeutic and perhaps even untherapeutic. It is a method of deconditioning that can be effective at rooting out the oppressive and limiting conditioning within capitalist society.