This study seeks to find out how Taiwanese businessmen (臺商) living in Shanghai perceive the two countries they are connected with, Taiwan and China, through investigating what strategies they employ when making decisions about their children’s education. In particular, the paper attempts to discern whether Taiwanese economic migrants face any psychological dilemmas regarding their ethnic-national identity in the context of the Cross-Strait; and if so, how they solve these dilemmas, given the tendency since 2000 for increasing numbers of Taiwanese businessmen to settle in Shanghai. The education system in China is divided into three categories: international schools, Chinese public schools and schools for Taiwanese businessmen. Taiwanese economic migrants working in large corporations tend to send their children to an international school, whereas those from the middle or lower middle class are more likely to choose either a Chinese public school or a school for Taiwanese businessmen. Among the latter group in particular, there is a trend towards ‘localization’ and a preference for Chinese local middle/highschools. Taiwaneseparents worry about whether their children will experience value-confusion while studying in the Guomindang-focused and communist-centered education system in China. Nevertheless, many are taking their children out of the Taiwanese schools and enrolling them in Chinese local schools instead. The reason for this, according to the evidence presented in this paper, is that they perceive Shanghai as a 'global' city and their own country Taiwan as ‘local’ government . They see Taiwan as a ‘nexus’ providing them with practical resources rather than ‘emotional stability’ or ‘ethnic-national belongingness’. They also view their homecountry as less internationally important than the ‘global’ city of Shanghai and therefore do not feel psychologically obliged to see Taiwan as ‘a place to go back’ or re-migrate to. Instead, they see Shanghai as a unique place unlike the other regions of China. Thus, the findings of there search were that whilst going through the process of selectin galocal school in Shanghai, Taiwanese businessmen did not any feel psychological obligation to choose Taiwan over China.