Purpose: In order to explore how informal pedagogical moments are being renegotiated by the technology woven into people's lives, this paper aims to focus on online communities as sites of learning; more specifically, the informal work-related learning practices of self-employed workers in these cyberspaces. Design/methodology/approach: This paper draws on the notion of legitimate peripheral participation (LPP) from situated learning theory in order to examine the development of work-learning practices online. Semi-structured interviews were conducted with own-account self-employed workers (contractors and consultants who do not have staff) about their engagement in online communities for work learning. Findings: Findings indicate that these self-employed workers were learning work practices, the viability of doing particular work, how to participate in online communities for work learning, and how to participate in fluid knowledges. The significance of developing a work-learning practice is emphasized, as is the impact of multiple and peripheral positionings across on- and offline spaces. Research limitations/implications: Web technologies and shifting configurations of online collectives shake up notions of expertise, beliefs about who is able to produce, and consume information, and where one locates themselves, in order to build work-learning practices. Multiple positioning across several online communities, and ways of participating that are peripheral, partial and part-time warrant further examination. Originality/value: The value of this paper is its exploration of how self-employed workers develop an online work-learning practice and the tensions that these practices bring. The paper also attempts to discuss the utility of LPP for contemporary learning practices.