Globally, self-employed people were among the hardest hit by the repercussions of the COVID-19 pandemic and faced hardships such as financial decline, restrictions, and business closures. A plethora of financial support measures were rolled out worldwide to support them, but there is a lack of research looking at the effect of the policy measures on self-employed people. To understand how different governmental financial support measures enhanced the resilience of the self-employed and improved their ability to manage the pandemic, we conducted a mixed-method study using policy analysis and semi-structured interviews. The documents described policies addressing governmental financial support in Sweden and Canada during the pandemic, and the interviews were conducted with Swedish and Canadian self-employed people to explore how they experienced the support measures in relation to their resilience. The key results were that self-employed people in both countries who were unable to telework were less resilient during the pandemic due to financial problems, restrictions, and lockdowns. The interviews revealed that many self-employed people in hard-hit industries were dissatisfied with the support measures and found them to be unfairly distributed. In addition, the self-employed people experiencing difficulties running their businesses reported reduced well-being, negatively affecting their business survival.