With Lilyana V. Petrova, we gave a performance at EASST-4S Amsterdam 2024 as part of the Artistic Research as Generous Practice session. Our proposal took the shape of a dialog between a therapist and a patient on intimate issues regarding trans-disciplinarity. This helped us explore the vulnerability associated with the sense of (not)belonging, the dynamic of boundaries between disciplines (metaphorised as moving coastlines with a clear reference here to climate change) and the related deleuzian notion of (re)territorialisation. We put strong emphasis on what makes generosity so different from tolerance, in as much as the former involves “giving up territory” (aka waiving it). In this view, generosity will “cost” us something, it cannot be free (be it financially or psychologically). Generosity thus involves much more than tolerance, namely, to welcome the Other in her radical otherness. How can we rethink technology as a way to mediate generosity far beyond mere tolerance and how can artistic research become transformative in this respect? Here we explored two crucial issues: how artistic research generates new forms of legitimacy in a context where legitimacy traditionally stems from hyper-specialisation; how it can reassess generosity as a democratic negotiation mediated by technology ?