Retirement presents a pivotal life transition that can offer both liberation and adversity. This qualitative study explores the personal experiences of Nigerian retirees, shedding light on post-retirement challenges. Using purposive sampling, an in-depth interviews were conducted involving two (2) focus group discussions with six (6) retirees as participants in each group, who are residents of Government Residential Area (G.R.A) Trans-Ekulu, Enugu State, Nigeria. The data of the study participants’ showed that majority served an average of 35 years in active service. Despite this, the study revealed that retirees struggle to balance their newfound freedom with (1) financial constraints, (2) health issues, (3) demands of family obligations, and (4) lack of proper records/profiling in active service. Also, participants expressed dissatisfaction of their pensions and gratuities arrangements, which are not properly managed by Pension Fund Administrators (PFAs). The study underscores the urgent need for comprehensive retirement education, transparent pension fund management, improved healthcare access, and institutional reforms aimed at easing the transition into retirement. Policy implications and suggestions for future research were examined to enhance retirees’ post-retirement success.