School to work transition is an important aspect of lifelong learning that has increased in significance as the knowledge-based economy takes off in developed countries. Rapid structural economic changes, the importance of innovation, and a shorter lifecycle of products require education systems to adjust to the needs of economies and individuals. Educational reforms in many countries aim to improve school students' readiness for their important move to post-school life. Countries organize different pathways for students following secondary school level that are designed to meet both students' demands and the needs of economies. This article explores Hong Kong students' aspirations and realities. Although the majority of students plan to complete the final year of high school and 91.5% planned to undertake the Hong Kong Diploma of Secondary Education (HKDSE) to be eligible for higher education, in reality a significant number of school leavers do not perform well and should undertake training for employment. In addition, many students who are eligible for tertiary education cannot be admitted to government sponsored universities due to the limited number of places. This article begins with a consideration of students' aspirations, and then outlines the realities of transition and current issues. It concludes with some suggested policy measures that could improve equity during this school to work transition period.