In this chapter, Angela Duckworth, Elisa New, and Ross Weissman reflect on William James’s ongoing influence on their work in the fields of psychology, literature, and education. This dialogue presents James not only as a subject of historical interest, but as a thinker relevant for a contemporary audience and their questions – whether a graduate student, professor, or educational leader. As such, Duckworth, New, and Weissman discuss how James’s writings have informed different stages of their own careers and their approaches to classroom pedagogy, scholarship, work beyond the academy, and much more. Central to this chapter is Talks to Teachers and how James’s psychological insights remain relevant, informing their engagement with students in the twenty-first century. In Talks, Duckworth, New, and Weissman find a model for teaching, interdisciplinarity, and the importance and means of reaching wider audiences.