This chapter exposes the deep cracks in narratives of social media leisure and amateurism. It looks at how forms of value-generating, gendered self-expression are rife in the social media world through blogs, vlogs, Instagram, and more. Though these activities are superficially framed as amusement and sociality, this chapter contends that many young women do not produce and promote content just for the fun of it. Rather, they approach social media creation with strategy, purpose, and aspirations of career success. Hence, this chapter explores some of the most salient conditions and features of aspirational labor: narratives of creative expression, relationship-building in online and offline contexts, and modes of individualized self-expression that both reveal and conceal normative feminine consumer behavior.