Starting from an emblematic episode described by Rorty in Trotsky and the Wild Orchids, which is an effective narrative example of making public a private experience, the article provides an inquiry into Rorty’s thinking around education, with a particular focus on his notions of contingency and luck.In particular, the article offers an analysis of Rorty’s frequent use of the term “luck,” in accordance with a literary (non-philosophical) method, which informs his understanding of the role and function of education and his (...) view of the educational process. The use of a literary method is useful to give shape and meaning to the contingency of human experience, creating a narrative thread to connect the past and present and make meaning of the present through the images of the past. Within this framework, Rorty understands “luck” as a specific and crucial condition that highlights the presence of an undetermined space within which education can make a difference in individual life. (shrink)