The development of career education in Joetsu City, a major city in Niigata prefecture in Japan, focuses on innovations in schools. In 1999, the word “career education” first appeared in Japan as an official educational nomenclature (Gong et al., Career counseling in Asian countries: Historical development, current status, challenges and prospects. Journal of Asia Pacific Counseling, 3(1), 9–33, 2013). A policy report entitled “The Future Vision on Career Education and Vocational Education at School” redefined career education as education which encourages career development by cultivating the competencies and attitudes needed to raise the social and vocational independence of individuals (Central Council for Education, 2011). The future vision on career education and vocational education at school.). While Japan has a 100-year history in vocational/career education, it is only in the last ten years that there has been a concerted push for career education in the schools (Mimura, Bulletin of Graduate School of Teacher Education Waseda University 8:19–34, 2016). Joetsu City’s career education exemplary practices show how a school system builds an educational base among stakeholders for a seamless program of work experience practices and learning. Joetsu City’s career education demonstrates an exemplary practice of how one city can revitalize its economy through regional cultural principles and sustainable educational change.