The Employment paradigm formed the dominant mode of development after the Second World War through to the late 1970s. Within this paradigm, labour was associated with formal full-time (male) employment in the capitalist market economy and subjectivity within the employment-as-identity nexus. However, the transformative forces of neo-liberal governance, American geo-political hegemony and the asymmetrical power of transnational capital have effectively terminated the Employment paradigm. This has triggered both unintended risks and a crisis of social reproduction. It is in this post-employment era that the social economy has emerged to form a significant challenge to existing understandings of labour and economy.In this dissertation I argue that a paradigm shift is underway from one defined under the rubric of Employment to a potential alternative theorized as Work. Utilizing a case study composed of organizations and workers within the Toronto social economy, I hypothesize that the prospective paradigm shift challenges both the binary of paid work/leisure that existed under the Employment paradigm and the understandings of economy and labour that underpin it.