Complex global challenges cannot be solved by one discipline alone; rather, there is a need for a united effort, bringing together experts from different fields, across industry and community. At the same time, factors such as globalisation and changing demographics are altering the organisation of graduate workforces and workplaces. It is increasingly apparent that the academy has a key role to play in supporting students to become responsive, resilient, and responsible graduates, employees, and citizens, able to practice deep disciplinary knowing, demonstrate strong interpersonal and problem-solving skills, and be capable of working confidently within, across and beyond disciplines. Despite efforts to move toward forms of education and knowledge that transcend disciplinary boundaries, barriers to realising meaningful and impactful transdisciplinarity remain. The translation of disciplinary values, cultures, and epistemologies across higher education institutions, together with notions of identity, collegiality, and disciplinary protectionism continue to reinforce siloed educational structures. As such, attempts to address challenges and propose alternative pedagogies often struggle within bureaucratic infrastructure, failing to move beyond tokenistic efforts. Design, a practice familiar with traversing disciplinary boundaries, offers a lens to explore new models of transdisciplinary education. This chapter presents a case study that shares three design-led interventions applied as part of a project that considered future models of transdisciplinary education in a higher education institution in Sydney. In the same way that designing for transdisciplinary education challenged disciplines to reconsider their role and place within the academy, design was a discipline also forced to negotiate the boundaries of its field. This chapter offers an honest account of the successes and failures of design in its attempt to transcend academic disciplines in a meaningful way.