In this reflective essay we examined the experiences of a group of students from a small liberal arts college in the United States on a study abroad program to the Marshall Islands to intern as preservice teachers in Marshallese schools. Specifically, we examined 32 students' critical reflections written once they returned from their programs. We interrogated their understanding of themselves regarding their privilege as American students and the inequality between the two nations. Through their teaching of Marshallese students, they deeply questioned the meaning of privilege, culture, identity, and community. We interpreted these experiences through the lens of transformative learning theory and the notion of constructive disequilibrium. When critical-transformative pedagogies inform these experiences, they nudge students out of their comfort zone and offer them opportunities to consider new possibilities that widen their life trajectories and develop global citizenship. We conclude with advocating for the importance of study abroad experiences.