The purpose of this phenomenological study was to explore the lived experiences of 16 retired teachers, 60 years and older, with pension benefits and had an involvement in a bridge employment. Through in-depth interviews of 10 informants and focused group discussion of six participants, the data were gathered and subjected to thematic analysis. The results revealed that the retired teachers decided to take bridge employment for reasons of financial security, passion for the teaching profession, pleasure and satisfaction, ease and simplicity, and need to be relevant and of service. Their coping strategies included making their bridge job simple and uncomplicated, planning and preparation, updating and relearning, being pliant and flexible, resourceful and creative, and securing family assistance and support. The insights they shared conveyed their self-realizations to be financially astute and prudent, internalize that retirement is just a phase in life, and continue to long for life’s meaning and significance, and celebrate life and move on. What is notable in this study is the participants’ being still active and generative, their resiliency to face the challenges, and their insights of wisdom, hope, and faith.