The COVID-19 pandemic is viewed as an emergent social phenomenon with several negative effects, e.g., financial decline of small businesses, as well as worsened sense of well-being. The aim of this article is to explore small business managers’ perceptions of governmental financial support measures and relate them to how they experienced their own health and consequences on their work environment. This mixed-method study was performed during the COVID-19 pandemic in Sweden. A survey was conducted during the period from October 2020 to February 2021 and answered by 729 small business managers, followed by ten interviews in March 2021. The key result shows that the managers were dissatisfied with the governmental financial support measures implemented. The results show that the attitudes of the small business managers towards the financial support measures may have had a negative impact on their subjective health. The study indicates a mismatch between the needs of small businesses during the COVID-19 pandemic and how society provides resources through support systems. This in turn may have meant a limitation on the government’s ability to assist small business owners with financial support during the pandemic.