The philosopher Richard Rorty once remarked that the genre of philosophy writing is an extended conversation that can be traced to the dialogues of Plato. All the foundational questions of philosophy can be found in ancient philosophy texts. The subsequent history of philosophy is a dialectic progression on these questions. I argue that reading the great works of philosophy and engaging in this conversation has something to teach us about autonomy, leadership and citizenship. Reading these works, and also great works of creative literature, nurtures the imagination and interiority, and cultivates perspective on world history, politics and culture. I first elaborate the genre and styles of philosophy writing and then argue for its relevance to a civic model of education.