Holistic well-being has rapidly developed in the 21st century as a policy measurement tool. Nevertheless, there continue to be some gaps in the literature regarding the interrelation between subjective well-being and other factors, and, regarding disaggregation of the well-being status within a country, by age group, gender, and community. This study first illustrates how the concept of well-being developed from a philosophical and psychological conception of “happiness” to being measured by multidimensional tools that measure the impact of policy and the progress of society, such as OECD’s Better Life Index, UK’s National Well-being Measurement, and Japan’s Well-being Survey and Quality of Life. Subsequently, it analyzes the relationships between subjective well-being and objective variables by comparing the country, regional, and individual datasets. It found that some indicators, such as social relationships, have asymmetric effects on life satisfaction depending on the income level or threshold. In other words, if the income is less than a certain level, the effects of some indicators on life satisfaction are complementary to income, while if the income is above that level, the effects are substitutional. Finally, it estimates these effects and confirms them statistically by using the OECD Regional Statistics. Regarding the relationship between social connection and self-evaluation of life satisfaction rated on a 10-point Likert scale, the base score in the estimation is approximately 5.1 points higher in the lowest quartile group of income. However, the substitution is lower than that of the other groups by approximately -0.061. The coefficient of social connection for the other groups was approximately 0.059, and the lowest group had almost zero coefficients for substitution.