As part of doctoral research into the history and impacts of the University of Newcastle’s Open Foundation Program (OFP) 21 experienced lecturers were asked about their memories and reflections of teaching into the program, which is now in its 45th year of operation. One question related to their philosophies of teaching in order to ascertain what beliefs and values may have influenced the delivery of OFP and whether there were any particular andragogical strategies they found useful to engage mature age students. Positioning their responses within Mezirow’s (1978) Transformative Learning (TL) theory, which focuses on the importance of perspective change and confidence building through critical self-reflection during the learning process, this chapter shares these lecturers’ insights into issues such as the importance of authenticity when teaching in tertiary preparation spaces, the relevance of cultivating a culture of care for these, often vulnerable, students as well as the need for adaptability and flexibility to respond to a diverse range of learners where ‘one size does not fit all’. These lecturers recognised the many checks and balances, identified by Dewey (1916) as “the problem of dualisms”, required for effective teaching of mature age students.