Emerging occupations involved in platform-based work face competing demands: they are not only expected to be authentic but also need to embrace entrepreneurialism to survive. The need to be simultaneously authentic and entrepreneurial has some inherent tensions, but prior research is unclear about how and when occupational members navigate such tensions. Through a qualitative study of an emerging occupation (content creators) involved in platform-based work, we examined this question. We identified three types of authenticity work—expressive, deflective, and protective—that content creators enacted, and found that as compared to expressive and deflective authenticity work, protective authenticity work enabled them to navigate the tension between authenticity and entrepreneurialism. Through protective authenticity work, content creators (a) layered the self into a “sacred” core, a marketable exterior, and a desacralized middle that involves vulnerable experiences that are emotionally or temporally distant; (b) blurred the boundaries of market and non-market spheres by bundling commercial exchanges with social exchanges through exposing the desacralized middle layer to the audiences. Together, these mechanisms of layering and bundling facilitated content creators to obfuscate their economic intention while passing as authentic in the eyes of the audiences, thus enabling them to navigate the authenticity-entrepreneurialism tensions in platform-based work.