As a youth, he worked as a guard to retired Emperor Toba, but in 1140 at age 22, for reasons now unknown,[1] he quit worldly life to become a monk, taking the religious name En'i (円位).

Yoshino, Ise, and many other places, but he is more known for the many long, poetic journeys he took to Northern Honshū that would later inspire Bashō in his Narrow Road to the Interior.

Where the Kokin Wakashū was concerned with subjective experience, word play, flow, and elegant diction (neither colloquial nor pseudo-Chinese), the Shin Kokin Wakashū (formed with poetry written by Saigyō and others writing in the same style) was less subjective, had fewer verbs and more nouns, was not as interested in word play, allowed for repetition, had breaks in the flow, was slightly more colloquial and more somber and melancholic.

[2] To be "heartless" was an ideal of Buddhist monkhood, meaning one had abandoned all desire and attachment: 心無き 身にも哀れは 知られけり 鴫立つ沢の 秋の夕暮れ Kokoro naki Mi ni mo aware wa Shirarekeri Shigi tatsu sawa no Aki no yūgure

[3] Saigyō travelled extensively, but one of his favorite places was Mount Yoshino, famous for its cherry blossoms: 吉野山 こぞのしをりの 道かへて まだ見ぬかたの 花をたづねむ Yoshino-yama Kozo no shiori no Michi kaete Mada minu kata no Hana wo tazunen