The common understanding of Chuang-Tzu as one of the earliest deconstructionists is only half true. This article sets out to challenge conventional characterizations of Chuang-Tzu by adding the important caveat that not only is he a philosophical deconstructionist but that his writings also reveal a non-relativistic, transcendental basis to understanding. The road to such understanding, as argued by this author, can be found in Chuang-Tzu’s emphasis on the illusory or dream-like nature of the self and, by extension, the subject-object dichotomy inherent in all forms of conceptualization and descriptive language. These two obstacles to true understanding - the self and literal, linguistic expressions - are overcome in the Chuang-Tzu by implementing metaphorical and poetic language, such as the Kun-Peng myth, the swamp pheasant parable, the introduction of physically deformed interlocutors, various dream analogies, and so forth. By employing such literary devices in a comprehensible and non-mystical manner, this article concludes that Chuang-Tzu successfully communicates his essential wisdom by guiding the reader to a higher state of spiritual awareness, a state in which one transcends the self, language, conceptual paradoxes, and even the idea of transcendence itself. Consequently, through the following explication of Chuang-Tzu’s complementary emphasis on both preventing mental rigidity and promoting spiritual transcendence, this article seeks to earn Chuang-Tzu the reputation of a deconstructionist with a difference.