Ozaki attended the prestigious Tokyo Imperial University, graduating on 16 October 1909.
An alcoholic, Ozaki witnessed the birth of the modern free verse haiku movement. His verses are permeated with loneliness, most likely a result of the isolation, poverty and poor health of his final years. Ozaki"s interest in haiku and writing began at an early age, and he was influenced by the pioneer of free verse style haiku, Ogiwara Seisensui, while still in high school.
Nearly immediately following the failure of this rejection, Ozaki"s heavy drinking, which would continue for much of his life, began.
Many writers believe that the rejection was the initial cause of his later alcoholism. (Ishi, p 56) Although he had previously been using the pen name of "Hōsai" written with the characters "芳哉", during this period he gradually shifted to using "放哉" (pronounced identically).
This change is perhaps significant, as the former character, which appears in Yoshie"s name, was changed to one meaning "to release, set free, banish, liberate."
After graduation, Ozaki joined the Nihon Tsūshin Company (日本通信社) in October, 1909, but was fired one month later due to incompetence. The following year, Ozaki joined the Tōyō Life Insurance Company (東洋生命保険会社), (the predecessor to Asahi Mutual Life Insurance Company) where for a time he led a seemingly successful career.
Shortly thereafter, one of his subordinates described Ozaki as "reeking of alcohol beginning each morning." (Ueda, p 81) During the same period, although all of the other employees wore business suits, Ozaki owned no clothing other than a tuxedo and a pair of pajamas.
He wore both to work. (Ueda, p 82) In spite of this, he was promoted to Contract Section Chief (契約課長, keiyaku kacho), likely due to well-placed connections. (Ishi, p 60)
Ozaki"s problems with alcohol continued to worsen, and he left Tōyō in 1920 at the age of 36.
In 1926, he settled on the island of Shodoshima, Kagawa Prefecture, in the Inland Sea, and was given the post of rector of the small hermitage of Minango-an at the temple of Saiko-ji.
With ties from his former life severed, and without any material possessions, he began to write haiku in earnest. His only anthology, Daikū (大空, Big Sky), contains poems of his solitary final months, and was only published posthumously.
(lieutenant is available in an English translation by Hiroaki Sato entitled Right under the big sky, I don"t wear a hat ().