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This article offers some comparative reflections on technology and the alienating potential of AI. These reflections are inspired by theoretical affinities between Daoism and Heidegger’s philosophy. In particular, I focus on the work Hypnocracy that recently sparked an international debate about the notion of authorship and the problematic relationship between AI-generated textual content and creative writing. The main thesis is that Daoism and Heidegger’s philosophy encourage a critical use of technology that rejects a reason dominated by sheer instrumental usefulness without rejecting technology as a whole. Ultimately, both philosophies favor the passage from the uncritical exploitation of technological affordances as mere means-to-ends to a deeper awareness characterized by an end-to-means, i.e., the equanimous releasement of purposive action expressing an ethics of relationality.