This article offers an analysis of the complex and contradictory nature of lay religious texts produced in England at the turn of the fifteenth century. These works are interesting because they include statements of both encouragement to and anxiety about lay Christians who pursue more singular forms of devotion. I focus on one text in particular, A Ladder of Foure Ronges by the Which Men Mowe Wele Clyme to Heven, a monastic treatise on contemplation translated into Middle English and adapted for a lay audience in the late fourteenth century, as a touchstone to consider these conflicting positions.