This chapter takes the form of an autoethnographic narrative engagement with the path that has led me to psychotherapy, and in particular to my role at as a senior lecturer in counselling and psychotherapy, at ACAP University College. By offering a thick-descriptive account of the landscapes, ideas, and thinkers who have formed me, I hope to suggest that the personal quest for well-being is one which requires a broader engagement with the existential and philosophical meaning of one’s role as a psychotherapist, and the broader systems in which we are inevitably embedded. I hope to highlight the continual relevance of these important yet neglected thinkers and ideas; to emphasise the need to understand well-being in relation to place; and to offer one reimagining of the pathway forward in mental health care. Such an approach to self-care is requisite if we are, as therapists, to embody and enact our lives in congruence with an understanding of well-being grounded in humanistic, psychodynamic, process-, systems-, and complexity-based perspectives. Our professions, as counsellors and educators, require that we give voice to the collective questions currently in formulation. What is called for is a reimagining of what it is to be human, what well-being truly means, and how the socio-political issues we are faced with today will shape the therapeutic landscapes of the future.