Over the past decade, work in the cultural sector has grown evermore precarious amid heightened competition, rampant insecurity, and the individualization of risk. Despite this, social media personalities—including bloggers, vloggers, and Instagrammers—seem to have attained a much-vaunted career dream: They get paid to do what they love. Accounting for this disparity, we highlight the role of popular media discourses that hype the possibilities of a career fashioned online. Our study draws on a qualitative analysis of more than 200 articles to reveal how these influencers circulate a patterned set of mythologies about creative work in the social media age. Such narratives about the fun, free, and authentic nature of their self-starter careers conceal less auspicious realities, including the demands for emotional labor, self-branding labor, and an always-on mode of entrepreneurial labor. Together, these myths help perpetuate an image of glamour in these industries as part of a “creativity dispositif” that both disciplines and incites cultural workers and aspirants.