Career guidance is attracting more and more attention in Asia as it is expected to secure “better employment” opportunities for students. The recent establishment of career guidance in TVET is closely related to the need to ensure the quality of TVET in such areas as enrollment, learning performance, employment, and on-the-job lifelong learning for students. Each area has specific issues and challenges that must be addressed when the system of career guidance in TVET is designed. This chapter examines a number of these common challenges, such as the low status of TVET in Asia and gender inequality issues during enrollment, “bad learners” as a target group for learning interventions, the unclear requirements of the labor market and complex unemployment problems, a large portion of the informal economy that influences school-to-work transmission, and the difficulties associated with designing possible career pathways across domestic and global job markets in the context of lifelong learning. Each of these concerns provides a clear direction for the areas that should be accounted for when designing a TVET career guidance system in the Asian region. The scope of the discussion is limited to career guidance in formal TVET at the senior high school level.