Retirement is a time when responsibilities are reduced and replaced by different kinds of outlets, but it does not logically match with the retirement age. In this study, phenomenological qualitative research design was utilized in order to comprehensively capture the over-all experiences of retiring teachers in the Department of Education, Division of Aklan, District of Makato. The findings showed that most of the participants experienced mixed emotions during their transition from their previous learned routines to their retirement phase. Most of the retirees suffered from psychological stress such as isolation and loneliness and lack of knowledge in proper planning and management of their financial aspects. To avoid further financial problems in the future, the participants pursued in settling debts responsibilities, which gave them peace of mind and rendered them to utilize time in creating more meaningful activities. As the participants ended their teaching occupation and being satisfied to the service they had contributed to the society, the feeling of fulfillment was achieved.