Self-employment (SE) is a growing precarious work arrangement internationally. In the current digital age, SE appears in configurations and contours that differ from the labor market of 50 years ago and is part of a ‘paradigm shift’ from manufacturing/managerial capitalism to entrepreneurial capitalism. Our purpose in this paper is to reflect on how a growing working population of self-employed people accesses social support systems when they are not working due to injury and sickness in the two comparable countries of Canada and Australia. We adopted ‘interpretive policy analysis’ as a methodological framework and searched a wide range of documents related to work disability policy and practice, including official data, legal and policy texts from both countries, and five prominent academic databases. Three major themes emerged from the policy review and analysis: (i) defining self-employment: contested views; (ii) the relationship between misclassification of SE and social security systems; (iii) existing social security systems for workers and self-employed workers: Ontario and NSW. Our comparative discussion leads us toward conclusions about what might need to be done to better protect self-employed workers in terms of reforming the existing social security systems for the countries. Because of similarities and differences in support available for SE’d workers in the two countries, our study provides insights into what might be required to move the different countries toward sustainable labour markets for their respective self-employed populations.