Due to economic instability and technological change in digital media industries, media organizations and educators have encouraged freelance media workers to see themselves as individual businesses rather than a class of workers that should collectively protect their rights and fair pay. This article examines how freelance media workers negotiate individualism and collectivism, producing a contradictory freelance class ideology. It is grounded in an exploratory critical political economy of communication and sociology of work approach. It is based on interviews with 21 freelance journalists and professional writers, considering how they discursively construct their work practices and coping strategies vis-à-vis their uses of digital technology and the structural factors that shape media industries. Through discourse, these workers produce a contradictory “e-lance” class ideology as both entrepreneurs who temporarily sell goods and services and activists who temporarily resist demands from clients that they give up their rights and pay.