Changes in the technological landscape and the political economy of news media have opened up new spaces for freelance journalism, particularly in multilingual spaces. Freelance journalists occupy a precarious position due to their place within neo-liberal logics, but at the same time, are less beholden to many of the political, social, and commercial pressures constraining reporting and editing in big media houses. Biographical sketches of three Chennai-based freelancers demonstrate different possibilities of engaging as a freelancer across languages.