|Abstract||This paper has arisen out of email conversations between us from June 2015 to the present, and centres principally on an exploration of the living contradictions in our practices - voluntary prison-visiting in Dublin, Ireland, and tutoring at the Open University (OU) based in the UK. We explore our values overtly in our extensive e-mail correspondence, as well as our fears, hopes, disappointments and triumphs. We pay close attention to each other’s concerns for compassion, tolerance, love and human equality, as we raise our own and each others’ awareness about the issues that concern us. In that pursuit we find ourselves looking at our living contradictions (Whitehead, 1989), and consequently explore how we can resolve them. During this process we recognise that we are involved in a process of peer-mentoring (Yamamoto, 1988) which enables us to support each other at difficult times. This process channels some deeper insights about the growth of our own humanity, and therefore, we are claiming, to improvements in our practice and in our understanding of the significance of what we are doing.