In this paper we will focus on data from bi/multilingual educators and discuss aspects of translanguaging as a Culturally Sustaining Pedagogy (Paris and Alim, Culturally Sustaining Pedagogies. Teaching and Learning for Justice in a Changing World, Teachers College Press, New York, 2017). The data from the bi/multilingual educators come from a recent qualitative research (Tsokalidou, SiDaYes! Πέρα από τη διγλωσσία προς τη διαγλωσσικότητα/Beyond bilingualism to translanguaging, Gutenberg, Athens, 2017) that aimed to bring forward the issue of translanguaging (TL) in the everyday life of multi/bilinguals. Our findings suggest that TL could function as a means of increasing the confidence and self-esteem of minoritized students, while offering them a feeling of normality and pride for their linguistic and cultural backgrounds. It also becomes clear from our data that going against the grain of monolingualism and mono-culturalism is a great challenge for all.