The Japanese system of transition from school to work has attracted much attention abroad and has often been praised for its efficiency. The reality of both its formation in the past and its transformation at present, however, seems not to be reported accurately in other countries. This examination of the processes of the formation and transformation of the Japanese transition system will demonstrate that the apparent efficiency of the system has been the product of several historical factors. Moreover, the drawbacks of this system are becoming increasingly apparent amid the recent, drastic changes in Japanese society. The aim of this paper is to describe the process of formation in the 1960s and the subsequent transformation in the 1990s of the Japanese system of transition from school to work in order to reveal the limits of its supposed efficiency.