This paper explores the notion of linguistic insecurity as a way of exploring the link between language ideologies and the subjective experiences of transnational workers in the new economy. Focusing on two contrasting ideologies that characterize how language and identity is understood under neoliberalism — the newer ideology which presumes a flexible link between language and identity, and the older ideology which posits an essentialist connection — this paper analyzes how a Korean mid-level manager working at a multinational corporation in Singapore deploys these ideologies in a narrative about his experience of transnational work, and discusses how such discursive practice can be understood in terms of linguistic insecurity.