Hagiographical writing promotes a vision of Egyptian monasticism in which pious ascetic figures are isolated from the world. Peter Brown highlighted the role of the holy man as patron, but nonetheless reinforced a traditional view of Egyptian monasticism based on his readings of works such as the sixth-century Aphothegmata Patrum. Surviving monastic correspondence, in contrast, demonstrates that there was a highly individualized approach to the monastic vocation. In this article, I turn to documentary material to consider the complexities of the early development of the movement. As a case study, I use the Greek and Coptic correspondence of a fourth-century monk called Apa John. My conclusion is that activities and behaviours described in the texts do not always accord with any known typology or ideal, but they are invaluable for exploring aspects of the early monastic impulse and the role played by the movement in wider society.