This study focused on vocational education in Japanese high schools, particularly technical high schools, which continue to produce a relatively large number of graduates who go on to employment, and referred to the experiences of graduates to explore the vocational relevance of technical high school education for their early career development. The results of the survey revealed that 1) graduates find it difficult to see the relevance between the content of their studies at technical high school and their jobs, 2) students feel that their experience of student guidance is more important for their early careers than their learning guidance, and 3) for female graduates, their experience of technical education has a side to it that reproduces traditional occupational gender norms. Based on the above results, we looked at the issues in research and practice in vocational education. In particular, the importance of research that considers the paradoxes surrounding the relevance of education and work was noted. The paradox is that curricula and discourses that emphasize the connection between education and work have a tendency to invite doubts about the connection.