Before becoming a monk, Anuruddha had worn beautiful clothes, slept on the softest bedding, and lived in comfort surrounded by servants. Now he found that wearing ragged robes, begging for food, sleeping outside, and other aspects of his new life of severe discipline were very difficult. But with stubborn perseverance, he finally became accustomed to the life of a monk, only to be assaulted by the fatigue brought on by such strict training.

Ananda and his older brother, Devadatta, who would become infamous for his attempts to disrupt the Sangha and for his many assaults on the Buddha, were among the six young Shakya nobles who, with the barber Upali, requested permission to join the Sangha. Although Upali and the others were ordained immediately, Ananda and Devadatta were not permitted to be ordained.

One scripture offers the following account of how Upali overcame his lowly birth to become one of the Buddha's disciples. When Shakyamuni was a hermit in an earlier existence, he once asked the palace barber to shave his head, but the barber refused contemptuously because of the hermit's wretched appearance. The barber's nephew, who was an inexperienced novice, condemned his uncle's unkindness and did his best to shave the hermit.