In this study, the life of Yun Bong Gyun, who had to face a life being a Korean in nature yet also in a position to serve the Japanese colonial authorities as a local official, is examined. During the occupation period, he was well aware of his dual and somewhat self-conflicting identity, but did not let that hinder his efforts of maintaining an active life, making himself an intriguing figure to this author. His career as an official working at the Japanese colonial offices, and the course of action he took during his tenure, clearly show that he was indeed a person with pro-Japanese attitudes and intentions. After starting his career as a junior clerk at local Myeon-class offices, he became a staff member of a governmental office and later served as the head of a cultivation team dispatched to Manchuria. His actions themselves testify to the fact that he provided the Japanese authority with full cooperation. But this side of his life was not showing everything that he was. And interpreting every actions of his as having been nothing but pro-Japanese would be over simplifying the matter, as such attitude would only prevent us from appropriately evaluating his life. Considering not only his actions (& the results of those actions) but also other sides or his personality as well, we can see the so-called middle area’ that should have been existing to everyone either resisting the system or cooperating with it during that time period. He had a philosophy perceiving the modern civilization, Japan and Korea as entities all in conflict to a degree yet also coexisting in a certain manner And while he supported the society's transition to a modernized state, he also occasionally revealed his own preference to maintaining his identity as a Korean and not a Japanese, an identity which was surely based upon his heritage in historical, geographical and linguistic terms. It may have been a minor trait of his, but it was still there nonetheless. That makes it imperative for us not to overlook such qualities when an evaluation of someone's actions or intentions(especially those of an intellect) is required, or an evaluation of the relationship between the general public and the colonial authority is necessary. It was the intention of this author to explain, with the case of Yun Bong Gyun, that there have indeed been certain 'middle areas', especially inside the process of someone’s making decisions or taking actions regardless of their being resistant or cooperative to the system. And indeed, utilizing such evaluation in analyzing the various facets of the Japanese colonial ruling of Chosun, brought some interesting facts to our attention, if this author may suppose.