In the years before this decade is out, small communities in the North Central region, and indeed throughout the United States, will need to prepare for the challenge of declining employment-to-population ratios. In the communities affected, the population seeking employment is expected to fall while the population who depends on others to produce goods and services will continue to rise. This imbalance could lead to a decline in living standards if the provision of goods and services is delayed or interrupted. This paper expands the understanding of this problem by examining a simple mathematical relationship—called the economic wellbeing formula—that establishes a relationship between the standard of living, productivity, and the employment-to-population ratio. This theoretical framework follows a simple logic and has established precedent in the field of economic growth and prosperity. The paper uses illustrations to enhance its appeal as a tool of economic education that could serve as an anchor for communities to organize their ideas and formulate strategies in preparation for the demographic and economic changes looming in the near horizon.