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Abstract: A common interpretation of early Daoist texts, such as the Daodejing and the Zhuangzi is that they give us resources to be more authentic. However, recently Moeller and d’Ambrosio (2017) have challenged this reading. They propose that Confucians argued that one should become authentic and sincere in one’s role through a process of self-authentication. In their view, Zhuangzi is explicitly against this Confucian sincerity, by forwarding an ideal of ironic detachment and playfulness. In this paper, I take another look at the Zhuangzi through the passage of Hundun and put Zhuangzi in conversation with French existentialism, notably Fanon and Sartre. Specifically, I look at Fanon’s philosophy of race and how persons of color can resist the objectifying white gaze. I argue that both Zhuangzi and Fanon give us a sense of our possibilities and freedom from constraints and roles. This authenticity is not sincerity in a role, but a playful exploration of oneself freed from societal expectations.