Purpose This study investigated – the demographic characteristics of retirees who sought not to be reemployed or join an organization but, instead, to be self-employed. This study verified self-employment by regional and/or educational features to determine the self-employment factors and the policies required. Research design, data, and methodology – Models and hypotheses were used to verify the conversion into self-employment depending on retirees’ demographic characteristics. This study investigated regions according to precedent studies and used SPSS 18.0 as follows. First, frequency was used to investigate the general characteristics. Second, a factor correlation analysis was done. Results – Hypothesis 1, which stated that, "retirees with low educational background often start a self-employed business," was significant. Hypothesis 2, which stated that, "retirees in metropolitan areas frequently start a self-employed business," was significant. Hypothesis 3, which stated that, "retirees in a megalopolis frequently start a self-employed business," was significant. Conclusions – A preliminary startup education was needed to lessen the losses. Retirees should have preliminary knowledge of actual self-employment conditions to be given a startup education.