At first he tried to live simply near his family's home, but became worried that they would disapprove and try to "reclaim" him. One day he encountered a former fellow Oxford student, John Dalton, who was willing to set him up in a cell with the necessary provisions.
A few years after leaving Oxford, while living an ascetic life on Dalton's property, he had his first mystical experience. He expressed the feeling of mystical experience as calor, canor, and dulcor. Calor was a feeling of heat. Canor was an experience of sound. Dulcor was a sweetness that accompanied both the feelings of calor and canor. A combination of these feelings was with him always after that, about which he says "I did not think anything like it or anything so holy could be received in this life."
Having attained this level of mystic expression, he left Dalton's cell and started to travel. We know he spent time in Hampole, sharing his experience with a Cistercian convent. He also visited Margaret Kirkby, whom he had set on the path to the anchorite life. He was able to cure her seizures by his presence.
He stayed near the Hampole convent for the rest of his life. He died there in 1349, possibly having succumbed to the Black Death, although by fall of that year the worst of the plague was over. He was originally buried in the convent cemetery, but later moved to his own chapel space because of the attention his grave drew: visitors and supplicants came to pray and make offerings; miracles were claimed to result.
In the 1380s, canonization proceedings were begun; many of the details of his life (other than details he included in his many writings) came from recording the anecdotes from people who knew him or had heard of him during the process of preparing a biography as part of the canonization process. The process was never completed, however, so he never became Saint Richard Rolle, although the Church of England commemmorates him on 20 January. In the Episcopal Church in the USA, he is commemorated on 28 September along with the mystics Margery Kempe and Walter Hilton.
His writings were so popular that over 450 manuscripts survive that were produced between 1390 and 1500. His writings were more popular than Chaucer. We can look at some of them next.