Since the start of the new century, basic and senior schools have started to encounter curriculum reforms, and vocational education has experienced substantial changes. Based on the changing context in the past 10 or more years, this study examines the issue of school-to-work transition from the perspective of the vocationalization of secondary education in Hong Kong. In addition to providing the results of different studies, three approaches are proposed. These approaches include enhancement of generic competencies through technology, introduction of lost-cost programs in less gender-specific areas, such as business studies, and emphasis on entrepreneurship education.