Manjirō went in 1872 to study in Tokyo on the grounds of Zōjō-ji, at the "Aborigine Education Facility" associated with the Kaitakushi (Hokkaido Development Commission).
From the special terminology of kamon, which refers to the cross shape as chigai (違い) and the dots as hoshi (星), he derived the name "Chigaiboshi" (違星).
In addition to helping with his father's fishing work, he did manual labor away from home in forestry and agriculture, but continued to meet with societal discrimination as an Ainu.
Perhaps from the severe pressure of demanding manual labor and discriminatory treatment, the already frail Iboshi fell seriously ill at 17, and from this point on came to take an interest in more ideological pursuits.
From this time on, Iboshi formed the culture group Chawashō Gakkai (茶話 学会) with other Ainu youth from Yoichi, including his childhood friend Totten Nakazato (中里凸天), under the guidance of his teacher Nara.
It was also around this time that Iboshi began producing haiku under the tutelage of Nara and the newly appointed teacher Kenji Yoshida.
He participated in gatherings of haiku poets in Yoichi and began submitting his work to the Tokyo poetry magazine Nihihari.
In February 1925, through the kind offices of Mitsujirō Nishikawa, Iboshi obtained a job as a clerk with the Tokyo Market Association (東京府市場協会) and was thrilled to move to the capital.
The picture she book painted of Hokkaido as a lost paradise of the Ainu impressed Iboshi, and that vision had a great influence on his later work.
Kindaichi invited Iboshi to the Tokyo Ainu Conference (東京アイヌ学会), where he gave lectures to scholars of some standing, including the folklorist Tarō Takayama and the "father of Okinawaology" Iha Fuyū.
Life in Tokyo gave Iboshi a steady job and chances to meet various celebrities and personages, as well as knowledge and experience from participating in various academic and lecture groups.
He left behind a prosperous year and a half in Tokyo to return to his birthplace of Hokkaido, resolved to save his fellows from poverty and discrimination.
However, conflict broke out between these two sponsors during Hokuto's stay, including Gotō's cutting funding to the kindergarten, and Iboshi was caught between them.
In the meantime, he worked with his old friend Nakazato to make a mimeograph fan magazine, named Kotan, which they completed in August.
Takeichi Moritake, who lived in Shiraoi and would later be counted among the three great Ainu poets with Iboshi and Yaeko Batchelor, first encountered Hokuto's work at this point.
He continued to draw attention as a poet, publishing tanka almost every week in the Otaru Shimbun and having a special edition of the Sapporo poetry magazine Shizuku (志づく) dedicated to a collection of his works.
The haiku poet Kenji Yoshida, who had been close to Iboshi, organized the manuscripts that had been in a traveling bag by his pillow and sent them to the Kibōsha.
In 1959 Kisaku Yumoto introduced Iboshi alongside Yaeko Batchelor and Takeichi Moritake in Poets of the Ainu (アイヌの歌人).
Kotan was included in the 1972 compilation Records of Recent Peoples 5: The Ainu (近代民衆の記録5アイヌ) from Shin Jinbutsu Ōrai-sha (新人物往来社), and in Rippū Shōbō Publishing's Complete Literature of Hokkaido (北海道文学全集), volume 11.