This document discusses how digital media is revisiting questions of gender and labor. It examines three cases - digital media professionals who work in women's magazines, digital media amateurs who blog, and digital media interactives who participate in user-generated content. For professionals, the work involves being a "jack of all trades" and is increasingly precarious. Amateurs strive to capitalize on their expertise and brand themselves. Interactives provide affective labor through commenting and forums that media companies then exploit for free. Overall, digital structures encourage overlapping forms of gendered labor around being accounted for, aspirational, and affective.