Rolle attended the University of Oxford but, dissatisfied with the subjects of study and the disputatiousness there, left without a degree. He established himself as a hermit on the estate of John Dalton of Pickering, but he later moved to other hermitages and probably always led a wandering life, rousing some opposition but winning much admiration. He kept in touch with a number of religious communities in the north and seems to have become spiritual adviser to the nuns at Hampole, in south Yorkshire, before his death there.

Rolle's importance lies in the devotional prose he composed in the vernacular for women readers. It is sometimes difficult to distinguish his writings from those of his followers and imitators. Those English or Latin epistles and treatises that have definitely been attributed to Rolle, however, reflect his fervent devotion and his emphasis on a rapturous mystical union with God. Throughout his writings the life of contemplation and solitude is exalted. Rolle's writings in Latin are overly rhetorical, but his English prose style is lively, flexible, and persuasive. His influence and reputation lasted until the Protestant Reformation.