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As media companies grow in profits and economic significance, workers in these industries are experiencing precarious forms of employment and declining union power. This article provides insight into the experiences of a growing segment of the media labour force in Canada: freelance writers, who face declining rates of pay, intensified struggles over copyright, and decreasing control over their work. At the same time, freelancers are currently experimenting with various appoaches to collective organizing: a professional association, a union, and an agency-union partnership. As part of a larger project on freelance writers’ working conditions and approaches to organizing, this article provides an overview of three organizational models and raises some early questions about their implications.