This chapter examines the way by which the fulltime social media producers articulated their work styles: they lauded the flexibility and autonomy of their pieced-together careers while drawing attention to some of the less glossy features of the independent work-style. Indeed, the social media professionals detailed careers marked by a chaotic pace of work, periods of insecurity, and the demand to be ever-present to both audiences and advertisers. These individuals thus engage in aspirational labor, albeit of a different sort: they labor persistently—and at times, invisibly—to maintain their status in the midst of a “political economy of insecurity,” where neoliberal ideologies and practices shift organizational risks and responsibilities onto the individual.