Walsingham's earliest works, including the Liber benefactorum and Prohemia poetarum, admit to wider audiences than those typically assumed for monastic discourse. While these texts—a record of patrons and a schoolbook, respectively— were designed primarily for use by the monks within the monastery, they also found secular readerships and were likely composed, in part, with those readerships in mind. Parts of the Prohemia circulated separately among enthusiasts of the genre of tragedy, and seemingly triggered Chaucer's satirical response in the ‘Monk's Tale’. And while the Liber benefactorum probably did not leave St Albans, it had at least one London auditor in Alan Strayler, who was brought in most likely on a long-term residential basis to work with Walsingham on the program of illustrations—not to mention those frequent visitors to the abbey who, having paid to appear in the book, certainly would have perused its pages to find their own portraits on prominent display. We cannot know if Walsingham himself distributed the copies of his commentaries on Lucan and Seneca, but it is extremely unlikely that he was unaware of this wider circulation and even less likely that he did not anticipate readers’ responses to the likenesses in the Book of Benefactors.

As Walsingham's career progressed, we find an increased willingness to insert himself more visibly into his texts, through playful self-identifications and additions of content related to his own interests, and an increased straying from his sources. We find also in his later work an inclination to explore, in more sustained fashion, literary genres and themes that fall outside of monastic conventions: the Historia Alexandri magni principis and the Ditis ditatus (or ‘Dictys enlarged’) are full-length compositions that treat two of the most popular secular literary traditions of the later Middle Ages, Alexander the Great and the fall of Troy. Even more than his earlier pieces, these works experiment with graduated understandings of authorial craft. Composed sequentially within the period of his most prolific production, sometime between 1380 and 1394, the Alexander and the Dictys suggest a manner of seeking, a wandering away from those forms of literary enterprise endorsed and circumscribed by the abbey's needs and toward the multiple and diverse textual traditions explored by secular literary communities— including vernacular romance, travelogue, and political allegory.