During Su Shi's periods of demotion and exile to Huangzhou, Huizhou, and Danzhou, his poetic and literary works reflect a contemplative acceptance and application of the concepts of "usefulness" and "uselessness" from Zhuangzi. The author aims to explore how Su Shi, in his works from this period, incorporates and adapts the philosophical ideas from Zhuangzi, comparing them to Zhuangzi's original thoughts. In Su Shi's works, the examination of "usefulness" and "uselessness" is not centered on utilitarian judgments or values based on practical purposes. Instead, it emphasizes the uniqueness inherent in all things, suggesting that the dichotomy of usefulness or uselessness is ultimately unnecessary. Su Shi's contemplation and utilization of Zhuangzi's ideas serve the purpose of maintaining a broad perspective even in adversity. Through this, he seeks to realize the Confucian aspiration of contributing to the world despite challenges. From a meta-perspective, Su Shi's acceptance and application of the philosophical discourse on "usefulness" and "uselessness" from Zhuangzi offer an explanation as to why he considers his experiences in Huangzhou, Huizhou, and Danzhou as significant achievements in his lifetime.