Background: Research demonstrating the positive outcomes of service learning among university students is robust and some describe the impact as transformative. Purpose: To help me better understand how I can support transformative learning in my classroom, this study explored how an intergenerational critical service learning project fostered change among student participants. Methodology/Approach: Data consisted of reflection journals collected over 6 years from 228 students who participated in a course-based intergenerational service learning project and researcher field notes. Using a qualitative design and narrative methodology analysis took place over a 2-year period and consisted of a 3-stage process: deep reading, identifying stories, and re-storying to generate findings. Findings/Conclusions: Three mechanisms were found to foster transformation among students—writing as inquiry, embodied learning, and mindfulness. The two-pronged contemplative approach used in this course informs the way in which students experience the critical service learning project. Together, they provide a deep and transformative learning opportunity. Implications: Insights into course design and pedagogical approaches that support transformative learning.