Poor role fulfillment among working students is a concern in schools and communities. Guided by William J. Goode’s Role Strain Theory, I explored the challenges, coping strategies, and insights of a working student through qualitative case study approach. Data collected from interviews were thematically analyzed. The finding revealed that the student encountered physical, cognitive, emotional, and social stress in managing her dual roles and coped through self-discipline, prioritization, emotional regulation, social support, and restorative practices. At the moment, the case has successfully established a personal business while continuing her studies. Furthermore, she gradually developed deeper realizations about resilience, perseverance, self-awareness, and personal growth. Future research may adopt quantitative methods to assess the impact of role strain and coping strategies on academic persistence and well-being, and develop measurement tools based on key themes to provide more targeted support for working students.