This paper provides reflections on transdisciplinary knowledge coproduction and experimentation processes from sustainability researcher perspectives. It centers on a 5-year period of collaborative research with small- and medium-sized enterprises in an Urban Living Lab in the Swedish craft beer sector. Nine reflections cover a variety of issues and potentials encountered during numerous interactions with societal partners, and are structured by three levels: organizational, interpersonal and intrapersonal. Based on the reflections, authors then propose a set of seven considerations and recommendations for how to more effectively collaborate in such transdisciplinary constellations. The recommendations apply across the three levels, and describe an approach to collaborative research that asks the researcher to be open, transparent, self-aware and intentional, reflective and reflexive, and both adaptive and flexible. Furthermore, they aim to create soft structures to facilitate understanding and mutual learning, such as designating “organizational champions”, as well as to embed collaborative reflections into recurring meetings with partners to maintain trust and capture sustainability knock-on opportunities as they arise.