This research explored the intergenerational dynamics of single motherhood by examining the lived experiences of single mothers who were raised by single mothers. Using a qualitative, phenomenological approach, in-depth interviews were conducted with a diverse group of participants to uncover how their upbringing influenced their identities, values, and parenting practices. Participants described the resilience, independence, and adaptability they developed while navigating financial hardships, emotional stress, and societal stigmas during childhood. At the same time, they highlighted inherited challenges, such as feelings of isolation and struggles with financial stability, which continue to impact their roles as mothers. These reflections revealed a heightened self- awareness of their efforts to balance their own aspirations with the responsibilities of single parenting. The study emphasized how intergenerational experiences shape personal identity, parenting styles, and family dynamics, pointing to the long-term ripple effects of single motherhood. Furthermore, it underscored the importance of targeted social support systems, policies, and community programs to alleviate inherited burdens and build resilience across generations. By highlighting these interconnected influences, this research contributes to a deeper understanding of the challenges and strengths in single- mother families, offering actionable insights for breaking cycles of adversity and fostering well-being.