Work facilitated through online labour platforms, such as Upwork or Fiverr, is an increasingly relevant source of primary or supplementary income for millions worldwide (Kässi and Lehdonvirta 2018). Whereas workplace learning activities of workers in conventional organisational settings have been studied extensively over the last years and are recognised as key determinants of work satisfaction and success, little is understood about if and how online freelancers learn and develop their skills during their platform-based work (Margaryan 2019). A recent report revealed that self-regulated learning behaviours may be particularly relevant to this population due to a lack of access to learning opportunities available in conventional organisational work and that one in three online freelancers (and up to three quarters in certain vocational categories) regularly uses online support communities, such as discussion boards, to facilitate their workplace learning activities or seek help (Cedefop 2020). This research aims to understand why and how online freelancers draw on online communities to facilitate their learning, particularly what topics they discuss in these communities and how these discussions contribute to their skill development. To this end, we apply natural language processing (NLP) and qualitative content analysis to a new textual corpus (N=10108) of the complete content posted to the “r/Upwork” and “r/Fiverr” discussion boards on Reddit between 2012 and 2020. Theories of self regulated workplace learning were not tested in platform work environments, raising the possibility that they may not directly apply to this new form of work without alteration. Studying the workplaces and social environments of online work will contribute to and develop this literature.