The aim of the article is to develop a phenomenological and theological approach to the affectivity of good teaching to foster a transformative practice of student engagement and awareness of the life of the soul as much as the mind and the heart. Drawing on the Catholic Intellectual Tradition's search for truth in the context of the theological virtues of faith, hope and love, the article sets out to articulate what it means to possess a thinking heart of education by way of engaging seven transcendental imperatives: be spontaneous, be imaginative, be hopeful, be faithful, be pastoral, be not afraid, and be vigilant. Together, these imperatives signify the transformative value of the search for truth evidencing a tradition of hopeful intelligence resonating with the affectivity of otherness, the turbulence and surprise of self-discovery, and a humble awareness of the wisdom of love at the service of love.