In this chapter, the authors present a much-needed quantitative study that examines the individual and interactive effects of individual freedom and national freedom on well-being among the elderly. The study analyzes cross-country data from World Values Survey and Freedom House. The result shows that personal freedom does not benefit well-being in a country that is not free. The authors demonstrate that it is possible to experience individual freedom in an unfree country, or conversely, to lack personal freedom in a free country. The authors further highlight the importance of ensuring the political and civil liberties of nations to promote happiness even if one has secured personal freedom.