Transformational learning theory is a cornerstone within the field of adult education. However, are all learners ready for their disorienting dilemma which instigates transformational learning? To answer this question, this autoethnographic paper unpacks an adult learner's personal journey on a research expedition to Antarctica. Using Antarctica as their disorienting dilemma, this reflective memo presents a critical self-assessment of unexpected feelings of grief and guilt experienced framed by the author's experiences as an adult learner on a research expedition. In doing so, the researcher explores the ways experiencing and unlearning grief and guilt are untidy and discursive emotions during a transformative learning journey. This paper considers how confronting grief and guilt can deepen the transformative learning process and reframes these emotions as lessons in the self. While the adult education discipline limits its interaction with grief and bereavement studies, this paper puts these emotions at the center of a learning journey to uncover just how Mad grief can be. [For the full proceedings, see ED666619.]