This article is based on a multi-site study of teachers in elite private schools in Australia. Teachers' accounts from this study bring nuance to the reasons one might short-handedly expect they have in working for these exclusive institutions. It is not that everyday motivations don't matter, for example, the financial compensations, the beautiful grounds and the status payoffs, but that teachers bring their own discourses, histories and intentions to bear on the contradictions of their work-lives. This is crucial evidence for understanding how privilege functions, how teachers are not simply co-opted or constrained. Instead, this article brings into view the agency of teachers who embrace privilege in spite of thorny questions around educational inequality that elite private schools cannot avoid.