In order for hope to be a sufficient state of mind, deliberate efforts, energies and actions are required in a way that embraces the other side of hope, namely, pain and/or despair. In other words, there must be an agreement that life consists of hopes/dreams and pain/despair. In the work of Duncan-Andrade, he gives us a reflective framework for our explicit and implicit hope and pain inside and out of the classroom. In this paper, we examine existing literatures related to hope theories and create a framework of postcolonial hope, we attempt to revisit Duncan-Andrade's audacity and robust hope that are used as an analytical tool for our explicit and elusive hopes inside and out of our professional contexts. Lastly, we offer a pedagogy with/for an understanding heart in pre-service teacher education intended to show a way in which we connect our present pain to our future hope.