Purpose: This paper aims to describe how a sustainability-focused program in higher education can provide training and key experiences for implementing transdisciplinary approaches. The case is a fieldwork-based training course called the Global Field Exercise (GFE) at the Graduate Program in Sustainability Science, The University of Tokyo. The GFE is a methodological training course that emphasizes generating locally relevant research questions on sustainability. Design/methodology/approach: This research is a case study regarding how a sustainability science program can offer a fieldwork-based training course that focuses on a transdisciplinary approach. Five students from diverse academic disciplines and cultural backgrounds participated in the GFE in QwaQwa where they conducted semi-structured interviews with six local entrepreneurs to identify the challenges and opportunities of entrepreneurship. The authors investigated the learning process and outcomes of the students through participatory observation in preparatory meetings, daily reflection sessions during fieldwork and a content analysis of feedback reports. Findings: Four learning outcomes of the students were suggested: the reexamination of assumptions, managing misunderstanding and miscommunication, mutual learning and being empathic toward the local people. Research limitations/implications: This paper suggests three key opportunistic experiences for the transdisciplinary approach: discuss the normative dimension of sustainability; build intersubjectivity among team members and adopt methodological pluralism; and become empathetic to diverse stakeholder groups to facilitate the cogeneration of knowledge. Originality/value: How to design training on a transdisciplinary approach in educational programs remains an area for further exploration. This study addresses this knowledge gap by establishing a link between sustainability education and sustainability in practice.