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Should one be in the service of the prince? What relationship should the literati have with power? Mencius and Zhuangzi, two major contemporary fourth century BC thinkers, provide two radically different answers. While Mencius sets prior conditions, Zhuangzi dismisses the very idea. According to Mencius – Confucius’ spiritual heir –, the deciding factor is the virtue of the prince, so that those who serve him can enable great achievements, rather than social rank, in determining this relationship. On the other hand, Zhuangzi, who holds a relativistic view of life and death, rejects service to the prince because one inevitably loses vital energy, while needlessly risking one’s life. In fact, he rejects any social bond restricting individual freedom. His attitude provoked the ire of the Confucianists, who accused him of misunderstanding human relations. Regardless, these two opposing and complementary views have had a lasting impact on the political understanding of the Chinese literati.