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This multiple case study explores the means through which freelance teachers establish their legitimacy in their classrooms outside of formal institutions. The data in this study were examined through the lens of Bourdieu’s (1986) social theory of capital and Van Leeuwen’s (2007) theory of authority. The perceived legitimacy of four core participants was examined using interviews, observations, and collection of artifacts. Native speaker (NS) and nonnative speaker (NNS) differences were found to be an important factor, and legitimacy was found to be highly context dependent, with some teachers constructing their legitimacy in contexts where being an NNS is advantageous. Some freelance teachers’ legitimacy is constructed around experience gained outside of the English language teaching (ELT) industry and through offering access to authentic second language contexts to their students. A minority of freelance teachers have identified pedagogical gaps in the ELT industry and have flourished in their own special market niches. The emic approach employed in this study shows that teacher legitimacy is more nuanced and context‐dependent than the simple NS/NNS dichotomy.