This article examines how we use notions and structures that challenge existing perceptions of mentoring, supervision and their relatedness to professional experience; and instead applies a sharply reconsidered analysis of the communicative space in which teachers and preservice teachers negotiate the phenomenon of ‘learning to be’ (Mezirow, 1991). We take the Habermasian concept of communicative space (1990) and earlier notions of lifeworld (Heidegger, 1962/1927; Merleau-Ponty, 1962/1945; Sandberg & Dall’Alba, 2009) as a theoretical frame to foreground learning and practice as ‘ways of being in the world’. A series of vignettes is presented to illustrate how mentoring is both epistemological (what we are learning to know or do) and ontological (how we are learning to be). It is this learning to be, in the teaching and learning to teach relationship, that we aim to identify, illustrate and elaborate in this chapter.One vignette illustrates a blended approach to mentoring that encompasses both epistemological and ontological perspectives. International and Australian research demonstrates the importance of teacher development of confidence and expertise for teaching the Arts imaginatively, and to embed quality arts processes and experiences across the curriculum (Ewing, 2015). This innovative creativity arts learning approach (Wade-Leeuwen, 2016; Barone & Eisner, 2012) builds on a community-of-practice model (Wenger, 2011) led by Arts educators at Macquarie University, Australia. These researchers were responding to an initial teacher survey that indicated 80% of preservice teachers in their final-fourth year of a Bachelor of Arts (Education) degree did not feel confident or competent to teach 21st century critical and creative thinking skills to primary aged children. Working in an intercultural community-of-practice framework allowed preservice teachers to examine these tensions through supportive mentoring processes where there was sufficient time for instruction, exploration and play, provocations and documentation, mindfulness and reflections (Edwards et.al. 2011, Langer, 2006). Notable increases in preservice teacher’s confidence and problem-solving capabilities were observed and documented over a five-year period (2011-2015). At the end of the study, all preservice teachers acknowledged a deepened awareness of their own artistic and metacognitive abilities. They voiced they were able to visualise how embedded principles of ‘learning to be’ in their own pedagogical practices enriched their critical and creative thinking skills. This vignette illustrates how nurturing a supportive environment through strong mentoring relationships between the mentor and mentee can alter their relatedness to professional experience.