Deciding between sustainability or prosperity may be a false choice when the phenomena are appropriately defined and considered together (Stiglitz et al. 2009). With reference to existing indicator systems and frameworks, including the Framework for Strategic Sustainable Development (FSSD) and the Community Capitals Framework (CCF), this research developed three novel indices (SMSI, SMSI+, and CCFI) using a Strategic Sustainable Development (SSD) approach to measure and analyze the correlation between sustainability (SMSI, SMSI+) and prosperity (CCFI) in Swedish municipalities. The spearman rank-order coefficient values were 0.259 and 0.588 for SMSI and CFFI and SMSI+ and CCFI, respectively. Both were significantly correlated with a p-value of 0.05, where SMSI+ and CCFI were 0.329 more correlated than SMSI and CCFI. This showed that an index that more comprehensively considers an SSD approach correlates more with CCFI. Furthermore, only six out of 234 Swedish municipalities ranked in the top 10 percent of both SMSI+ and CCFI, showing that it is difficult to successfully pursue sustainability and prosperity together in practice. Importantly, this research also demonstrates that it is possible to create indices using an SSD approach while outlining the methods for how to do so.