At present the earliest writing that survives from Richard Whitford's large body of work is his 1525 translation of the Augustinian rule (STC 922.3). Though he had entered religious life probably in 1511, the year of his will, his activity in the following fourteen years has not been traced, and this silence stands in sharp contrast to the flood of his publications in the later 1520s and the 1530s. Yet there is much to be said about Whitford's first years at Syon, a period, for him, as active as the better-known conclusion of his career. During this time the monastery was ruled by Abbess Elizabeth Gibbs (1497–1518), whose influence on Whitford he twice commemorated after her death and whose promotion of formational reading for Syon nuns was extensive.

Whitford's arrival at Syon would have come a little more than halfway through the tenure of Abbess Gibbs, and his recollections suggest that she was the force behind two of his early works. His A Dayly Exercyse and Experyence of Dethe does not survive before an edition dated [1534?] (STC 25413.7), but in this edition's preface, since Whitford recalls that he wrote it ‘more then .xx. yeres ago at the request of the reuerende Mother Dame Elizabeth Gybs … And by the oft callyng vpon and remembraunce of certayne of hyr deuout systers’, its composition may be dated around 1513. (Whitford adds that he has lately written the work out many times in response to requests and now is moved ‘to put it in print’.) Likewise in the Book of Patience, published as part of Whitford's final work in 1541, he says ‘I wrote this worke many yeres ago (as I sayd of ye werke of deth) & by lyke occasion’ (fol. A ii), that is, at the instigation of Elizabeth Gibbs. Because Patience refers to ‘your draft of dethe’, Patience is probably subsequent to that work, perhaps around 1514. Finally, Whitford's Werke for Housholders, though it is not connected explicitly with Abbess Gibbs, was also written earlier than its publication date would indicate. The first surviving edition of Werke is dated [1530?] (STC 25421.8), but James Hogg has pointed out that Dethe contains two references to Werke, which must thus have been written before c. 1513, possibly, as has been suggested, before Whitford's c. 1511 entry into religion.