Understanding the encounter of different generations may be a determining factor in the success of organizations. In order to have a clear understanding about the new generation, this article examines the working encounter of Generation Y. Generation Y in the Hong Kong Special Administrative Region and four cities in mainland China were studied. How the social environment influenced their attitudes and behavior in work and geographical mobility, and how geographical mobility created problems to the migrants were studied. We find that the Generation Y in Hong Kong is facing more competition than the Generation Y in mainland. In geographical mobility, most of the respondents accept geographical mobility. The findings provide some insights on how the social environment shapes the generation.