Shiki is regarded as a major figure in the development of modern haiku poetry,[3] credited with writing nearly 20,000 stanzas during his short life.

[6][7] Shiki, or rather Tsunenori (常規) as he was originally named,[8] was born in Matsuyama City in Iyo Province (present day Ehime Prefecture) to a samurai class family of modest means.

[12] At age 15 Shiki became something of a political radical, attaching himself to the then-waning Freedom and People's Rights Movement and getting himself banned from public speaking by the principal of Matsuyama Middle School, which he was attending.

[14] The young Shiki first attended his hometown Matsuyama Middle School, where Kusama Tokiyoshi, a leader of the discredited Freedom and People's Rights Movement, had recently served as principal.

[16] While studying here, the teenage Shiki enjoyed playing baseball[17] and befriended fellow student Natsume Sōseki, who would go on to become a famous novelist.

[19] But by 1892 Shiki, by his own account too engrossed in haiku writing, failed his final examinations, left the Hongō dormitory that had been provided to him by a scholarship, and dropped out of college.

"[24]) Contemporary to Shiki was the idea that traditional Japanese poetic short forms, such as the haiku and tanka, were waning due to their incongruity in the modern Meiji period.

[21] A month after completion of this work, in November 1892, he was offered a position as haiku editor in the paper that had published it, Nippon, and maintained a close relationship with this journal throughout his life.

[30] These three are Bokujū Itteki or "A Drop of Ink" (1901), Gyōga Manroku or "Stray Notes While Lying on My Back" (1901–1902), and Byōshō Rokushaku or "A Sixfoot Sickbed" (1902).

[33] Still in Matsuyama in 1897, a member of this group, Yanigihara Kyokudō, established a haiku magazine, Hototogisu,[5] an allusion to Shiki's pen name.

[32] Shiki may be credited with salvaging traditional short-form Japanese poetry and carving out a niche for it in the modern Meiji period.

[39] He argued that haiku should be judged by the same yardstick that is used when measuring the value of other forms of literature — something that was contrary to views held by prior poets.