This chapter focuses on the personal experiences of collaborations based on academic–practitioner interactions, which are not always as straightforward as presented in commonplace transdisciplinary theory. By using autoethnographic methodology, this chapter provides some of the most important insights from past and ongoing work from a major sustainability project that uses the ‘Research Forum’ (RF) as a new a means of co-production of transdisciplinary knowledge. The reflections center on the most common modes of interaction observed between academics to practitioners, but also on the pros and cons of everyday work in a overtly transdisciplinary context. The findings reveal that transdisciplinarity is neither a business deal nor a display of unconditional democracy. It is a tricky form of collaboration that takes time, energy and trust to understand, and this level of maturity may be difficult to obtain using the commonplace project format.