The purpose of this study is to investigate how five well-being characteristics from Positive Psychology are related to the FSE beliefs of older adults: positive emotions, engagement, relationships, meaning, and accomplishment. This study builds upon existing literature by examining how psychological and social environmental factors shape FSE beliefs using theory and literature from Positive Psychology. Furthermore, financial planning researchers predominantly use observed scales to measure psychological constructs; this study demonstrates how a confirmatory factor analysis is employed within a structural equation modeling framework to measure psychological constructs and more effectively manage error with a large dataset commonly used in financial planning research—the Health and Retirement Study.