Worried by the seemingly unending plight of retirees after years of active service to their father land, the Federal Government of Nigeria began tinkering on elderly entrepreneurship as a sure way out. Certain critical factors, worth empirical investigation are important to successfully transit from a retiree to entrepreneur state. Adopting the survey design, this study ascertained the major precursors of successful transition from paid employment to selfemployment in Nigeria. Relevant primary data were obtained through the use of structured questionnaire. This was administered on one thousand three hundred and twenty-two (1,322) civil service retirees during their annual pension claim verification exercise. Descriptive statistics (mean and standard deviation) and multiple regression were used to delineate the precursory factors and analyse their relationship with retiree entrepreneurial success. We found statistical evidence that post-retirement entrepreneurship success is significantly influenced by seven out of the twelve success factors evaluated. These included gratuity payment, positive peer attitude, and family size. The study has policy implication.