The purpose of this study is to investigate the lived experiences of four mature students, Rob, Rosemary, Charlotte and myself (all over 45 years of age) and our return to learning to pursue a professional teaching career. Given the influx of mature learners at the postsecondary level, sometimes referred to as ‘third age’ students, more attention is needed on the experiences of this population, particularly in fields of study like teacher education, which has historically targeted younger students. From our stories of returning to learning, three themes emerged that defined our experiences: relationships, values and challenges. Based on these themes, the complexity of being marginalized due to age, yet privileged due to life experience, came to the forefront. As mature learners, we experienced transformative tensions that suggest shifts in postsecondary education are warranted in terms of life-long learning and the capacity of institutions to provide the kinds of personal and professional support needed for mature student success. With particular attention to holistic education, our stories highlight respect, empathy and compassion for others, from which core concepts of duality, ambiguity, dialectic, power dynamics and living curriculum emerged as outcomes of this study. Examining the lived experiences of mature learners in higher education allows rich transformative experiences and innovative learning perspectives to develop concerning the understanding of self, education, and classroom communities, and by extension, creation and transformation of a learning society and culture.