The aim of this article is to examine some of the difficulties, paradoxes, and challenges involved with developing community-based collaborative artistic and pedagogical practices, both in museums and galleries and within the context of the so-called educational turn. The author, who is a scholar and educator at the Es Baluard museum (Spain), focuses on one concrete case in which she has been involved, together with renowned artists, in collaborating with a group of sex workers. This article presents the findings of this case study, which was conducted from a phenomenological approach, in order to reflect on the complexities and potentialities that arise when running programs of such kind. Going beyond the rhetoric of success in which practices are usually represented, it gives the reader important keys towards developing horizontal relationships between cultural institutions and the communities they are situated in. The analysis is undertaken using the framework of critical mediation and the concept of "contradicting oneself", as stated by theorist and educationalist Carmen Mörsch, wherein the mediator's positionality is a key aspect.