Research on caring teaching is not a new phenomenon. However, much of it relates to primary or secondary education levels, with only a small focus on the tertiary environment. This personal experience narrative follows the journey of a past secondary teacher whose teacher identity hinges on relationship building and a caring philosophy. Through a stressful period of burnout and personal introspection, the author then took a chance on following a different caring pathway within a regional university enabling course. This paper highlights commonalities and differences between being a caring teacher at the two levels of education, finding more commonalities than differences, and thereby opening up the potential for further research into the experiences of educators who have familiarity in both the schooling and higher education sectors.