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The general rise in contractors, particularly among knowledge workers negotiating ‘boundaryless’ employment conditions, has generated interest in the nature and forms of contract work. This article explores the learning of contract workers as they negotiate these conditions, with a focus on women. Drawing from a qualitative study of women practicing nursing and education in Canada as self-employed contractors, the discussion focuses on the practices that they learn in order to manage their work activities and identities. In these practices, tensions abound - particularly around the recognition of knowledge in ways that establish the contractor’s identity, position within the organisation, and market value. For women, it is argued from the study findings, boundaryless contract work incurs particular gendered demands that embed contradictions that the contractor must learn to negotiate. This article describes five practices that women contractors learn within these contradictions: (1) being noticed while avoiding notice, (2) nailing down contracts without nailing the contractor, (3) performing a woman in control while hiding the chaos, (4) shape-shifting while ‘branding’ one shape, and (5) proving knowledge in a market of impressions. The article concludes with implications for education that might assist women contract workers.