This paper reports on some initial results from an institutional research project regarding real world learning and dilemmas of practice in a tertiary art and design faculty. A dilemma’s framework informs the design of the study as much contemporary literature within higher education emphasises the importance of equipping students to work with, cope and become resilient when working with ambiguity, ‘liquid modernity’ and troublesome knowledge. The implication is that this theoretical perspective has significant implications for educators in examining their own practice by interrogating existing beliefs, routines and mechanics of becoming ‘professional’. Ambiguity, tension and risk are familiar concepts in art and design practice, and within the wider educational context the value of Deweyan educational encounters with disequilibrium is also well documented. This presentation reflects on responses from students in the middle of their first semester in Year 1 and Year 2 in a tertiary art and design school, to investigate challenges of beginning creative professionals. This data informs a larger research project about re-examining transitional moments of identity formation using critically reflective tasks. To investigate the beginning stages of creative professional lives, snapshot of data will be presented from an online qualitative research survey with 80 respondents in an art and design university faculty in Sydney, Australia. The responses generated from the student cohort revealed diverse statements disclosing nuanced kinds of ambiguity, confidence and trust.When focusing on challenges and transitions for creative students some emergent dilemmas from the research include inaccurate definitions, lack of shared language narratives, poor communication, private talk versus public talk, non-alignment of self with definitions, novice understandings of expert selves and positioning of career aspirations as unachievable. The challenge within creative professional contexts aligns well with Cherry (2014) who calls for a continuous recalibration of engagement with the dynamics of complexity. Data and key words from the initial survey such as ‘confusion’, ‘unsure’, ‘frustration’ and ‘put down’ were identified as important in recognising student engagement with complex learning dynamics in creative fields. Revealing layers of complexity informs how students regard themselves and their relationship to ambiguous learning encounters within ecologies of practice. Exposing ambiguity and working in constructive ways moves feelings of being ‘stuck’ towards viewing uncertainty and confusion as catalysts, prompting shifts from disequilibrium to understanding early in students’ professional lives.