The purpose of this study is to examine how the relation between general education and the world of work was structured, and what supported it in the early Showa Era, when the relationship appeared, through an analysis of the state of vocational guidance in primary school. Section 1 points out that the "Japanese" pattern of transition from school to work dates from the prewar period, and that earlier studies only clarified the intention and the actual situation on the part of companies or employment agencies. However, in order to grasp the entire historical process of the structuring of the system, it is necessary to elucidate the intention and the actual situation on the part of schools, and to inquire again on the issue of transition as a problem of education. The paper then explains the significance of clarifying the problem mentioned above. Section 2 examines the opinion of the Ministry of Education on the introduction of institutions for vocational guidance, and considers the kind of problems that occured in school. It shows that setting up a special subject of vocational guidance has consistently been shelved although teachers thought the problems emerged because of the lack of such courses. In the background was an essential aporia regarding vocational guidance. The aporia was caused by the fact that the transition from school to work was not always successful even if vocational aptitude tests were complete, because it depended on the situation of the labor market. Section 3 clarifies that two methods for giving vocational guidance in primary schools emerged. The two methods were as follows: (1) directly helping students to find jobs, (2) cultivating a "spirit of enterprise." In addition, the paper points out that this divergence corresponded to an aporia in vocational guidance, based on "ideal" versus "reality." These methods led to the development of the relation between general education and the world of employment in postwar times, with "continuity in system" and "discontinuity in substance." Section 4 discusses "Love," which was used to support vocational guidance in school. "Love" was a magic word used to justify both methods, and to hinder any examination of the methodology of vocational guidance. The paper then argues that "Love" was the trigger for the emergence of the issue regarding transition as a problem of education. Section 5 is a summary and discussion. It points out that the divergence of methods for giving guidance was an inevitable result considering the matter of transition as a problem of education. Moreover, it hypothesizes that the two methods of vocational guidance in school were united by the justification of the practices using the word "Love". The word "Love" continued to be used in postwar times.