Transdisciplinary learning is a response to address the comprehensive sustainability competencies for implementing the 17 sustainability goals of the Agenda 2030. Transdisciplinary contexts include socially distributed knowledge beyond scientific boundaries. This impacts the whole design process and specific tasks and roles of the researchers. Addressing the questions, “Which typical tensions, dilemmas and paradoxes need to be faced by researches in transdisciplinary settings?”, and “How does the role of the researchers change and goes beyond traditional research settings when operating in transdisciplinary settings surrounded by tensions, dilemmas and paradoxes?”, answers will be provided following existing analytical frameworks of transdisciplinary research design. Based on own experiences with and including observations of transdisciplinary settings at academia, transdisciplinary research and lecture settings will be analysed and compared by transdisciplinary criteria. Results show, in transdisciplinary settings, researchers or lecturers are more engaged with addressing poly‐contextuality, the consciousness of the innovation paradoxes and the side‐effects of ongoing interdependences. They take up multiple roles and have to deal with role ambiguity. Transdisciplinary lecture settings are even more demanding as they also have to meet the mentor role or maintain the students' learning progress.