This paper explores the context of "wandering" in the works of Chu Tien-Hsin and Huang Guo-Jun, two authors from different generations. Both writers, influenced by the external world, turned to writing about their inner worlds, using "wandering" to narrate the self and express their inner thoughts. However, the connotations of "wandering" differ between the two. Social environments provide inspiration and opportunities for creators, and this paper argues for observing the works of Chu Tien-Hsin and Huang Guo-Jun within their generational contexts. By doing so, the paper examines the differences between the two, exploring the generational transformation of "wandering".