Gender gaps in representation in Science, Technology, Engineering and Mathematics (STEM) fields persist across many societies, although the size of the gap varies. Based on cultural psychological perspectives, we consider how the culturally ascribed meaning and purpose of academic choice (i.e., as a means of expressing the self or securing one's future) can inform students' STEM interest and motivation as a function of their gender. We argue that a self-expressive construction of academic choice may lead men and women to diverge in their academic choices, since their preferences have been gendered throughout their lives. Specifically, a focus on expressing the self can push women away from STEM, and men toward it, given that it is considered a masculine domain. On the other hand, a security-oriented construction of academic choice may lead men and women to show similar levels of motivation to pursue STEM due to its potential lucrativeness. In two experimental studies, we examined whether temporary activation of goals related to self-expression or future security affect STEM interest and motivation as a function of gender among American students. Study 1 documented that the activation of a self-expressive construction of academic choice led to lower STEM interest and motivation among women compared to a control condition. Activation of security goals led to greater STEM interest and motivation among men only. Study 2 partially replicated this pattern for STEM and Business fields using a regulatory focus manipulation. The studies provide initial evidence for the role of culturally shaped understandings of academic choice in gender gaps in academic motivation. We end with a discussion on the sociocultural shaping of academic choice among both women and men.