The transition from school to work is a critical milestone in the life of young people and plays a crucial role in how their future careers develop. This transition is a complicated process which not only involves a change of identity from a learner to a worker, but also a transition from adolescence to adulthood where one's life planning is at stake. This paper examines the views of young Chinese in relation to career development in a society where East meets West. The study is a qualitative research with an in-depth semi-structured interview approach to explore the career concerns and issues faced by the post-80 generation in Hong Kong. Data is collected in audiotaped individual interviews with 10 young people aged 18 to 24. The sample is selected purposively in terms of their socio-economic backgrounds and thematic analysis is used to explore a number of key themes including ideas about career development, readiness for continuing education, constraints to career planning, gender differences in acceptance of cross-border work and overtime work, and single child problem for career development. The findings revealed insights on the career development of the post-80 generation and the interplay of ecological system in the Hong Kong context. Practical measures to facilitate a better transition to young adulthood were discussed in the paper as well. The insights from this study would be useful for human resource practitioners, policy makers and interested parties who together can jointly devise appropriate career interventions to assist young people in their transition to adulthood.