Although job availability in Japan is at its highest in 24 years, the unemployment rate has remained unchanged. On one hand, certain fields are saturated with employees while on the other hand, the rural areas of Hokkaido are in desperate need of agricultural workers. At the same time, the aging population in Japan is an emerging challenge. The flat unemployment rate in conjunction with the rapidly aging farmers’ population can possibly reduce the food self-sufficiency rate, raise Japan’s dependency for international food products and increase import expenses. Thus, these factors can tip the socio-economic balance of the struggling economy. For the present research, different surveys were conducted not only in various farming corporations of Hokkaido but also 20 farmers were directly contacted and interviewed. In addition, adolescents’ (aged 16–18 years) career choices were studied through questionnaires administered to 157 students at Hokkaido’s Sapporo Kaisei Secondary School. It was found that, in rural areas of Hokkaido, relocation of youth to the cities is probably the main cause of the shortage of workers. In Sapporo city, among adolescents who had already chosen a career path, around 76% wanted to enter the science and technology field. This trend can result in intense competition and “saturation” in science and technology fields and many vacant slots in the others related to agricultural farming. This behavior is probably maintaining the unemployment rate, regardless of the number of job vacancies. In addition, according to our survey, considering career paths, parents and teachers provide general guidance that has very little influence on adolescents’ career decisions. So, a more detailed career counseling is suggested.