During his stay in Japan from 1921 to 1925, Chun-Mu Hsieh has gradually transformed himself from a literate young man with careful thoughts to his homeland to an active campaigner. He has also turned himself from a progressive youngster under culture enlightenment into a person devoted to socialism campaigns for farmers and workers. This article took the knowledgeable elite Chun-Mu Hsieh's studying experience in Tokyo during the period Taiwan was ruled by Japan, as an example. Based on some of Hsieh's representative creations and works in the decades of 1920 and 1930, and also his participation in opposition movements in the colony, this article explored the track of the change of his thoughts before and after his journey to Japan. It demonstrated the self-onsciousness of Chun-Mu Hsieh as an organic intellectual in the colony, the implication of his "Tokyo expectation" for the purpose of home country innovation, and also the continuity and variability of his thoughts from "Proceeding to Tokyo' to "Farewell to Tokyo". Hopefully this case could point out how some young people in Japan, due to self-consciousness, turned their experience of studying abroad to an out-of-tune journey departing from an empire.