In this study, collaboration has been revisited between an American faculty member and an international graduate teaching assistant during a unique faculty-student mentoring model within principles of chaos theory. The role of culture, beliefs about language learning and teaching had been studied closely to improve faculty/international students' cooperation in academic settings. The research focused on the nature of the collaborative experience of a faculty member and a graduate teaching assistant in designing and implementing an authentic language learning experience into a graduate level linguistic course and the role of dynamism and chaos theory evident in this mentoring model. Participants engaged in collaborative planning of a language learning experience embedded into a graduate level linguistic course. Reflective journals of participants and assignments were analyzed to better understand the experiences of the collaborators and the ways their culture, beliefs, and mentoring model impacted andragogical choices for instruction and learning of participants and students. Through self-study, the researchers explored their professional identity and their academic flexibility within the organizational boundaries. The results of the study unveiled the complexity and chaos of each phase of cooperation and how the participants applied flexibility to achieve a more linear teaching/learning process. The collaboration between American faculty and international GTA under the shadow of chaos twisted by culture, beliefs, and hierarchy could still generate novice andragogical practices in higher education to contribute implications for collaborative work across cultures and hierarchies.