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. Around this time he developed an interest in moving to Tokyo and did so in 1883.

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. In 1883, a maternal uncle arranged for him to come to Tokyo. Shiki was first enrolled in Kyōritsu Middle School and later matriculated into University Preparatory School. (Daigaku Yobimon) affiliated with Imperial University (Teikoku Daigaku). While studying here, the teenage Shiki enjoyed playing baseball and befriended fellow student Natsume Sōseki, who would go on to become a famous novelist.

Shiki suffered from tuberculosis (TB) much of his life. In 1888 or 1889 he began coughing up blood and soon adopted the pen-name “Shiki” from the Japanese hototogisu—the Japanese name for lesser cuckoos. The Japanese word hototogisu can be written with various combinations of Chinese characters, including 子規, which can alternatively be read as either “hototogisu” or “shiki”. It is a Japanese conceit that this bird coughs blood as it sings, which explains why the name “Shiki” was adopted.

He entered Tokyo Imperial University in 1890. 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. Others say tuberculosis, an illness that dogged his later life, was the reason he left school.

Despite an atmosphere of decline, only a year or so after his 1883 arrival in Tokyo, Shiki began writing haiku. In 1892, the same year he dropped out of university, Shiki published a serialized work advocating haiku reform, Dassai Shooku Haiwa or “Talks on Haiku from the Otter’s Den”. 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. In 1895 another serial was published in the same paper, “A Text on Haikai for Beginners”, Haikai Taiyō. These were followed by other serials: Meiji Nijūkunen no Haikukai or “The Haiku World of 1896” where he praised works by disciples Takahama Kyoshi and Kawahigashi Hekigotō, Haijin Buson or “The Haiku Poet Buson” (1896–1897) expressing Shiki’s idea of this 18th-century poet whom he identifies with his school of haiku, and Utayomi ni Atauru Sho or “Letters to a Tanka Poet” (1898) where he urged reform of the tanka poetry form.

Suffering from the early symptoms of TB, Shiki sought work as a war correspondent in the First Sino-Japanese War and, while eventually obtaining his goal, he arrived in China after the April 17, 1895 signing of the Treaty of Shimonoseki. Instead of reporting on the war, he spent an unpleasant time harassed by Japanese soldiers in Dalian, Luangtao, and the Lüshunkou District, meeting on May 10, 1895 the famous novelist Mori Ōgai, who was at the time an army doctor.

Living in filthy conditions in China apparently worsened his TB. Shiki continued to cough blood throughout his return voyage to Japan and was hospitalized in Kobe. After being discharged, he returned to his home town of Matsuyama city and convalesced in the home of the famed novelist Natsume Sōseki. During this time he took on disciples and promulgated a style of haiku that emphasized gaining inspiration from personal experiences of nature. Still in Matsuyama in 1897, a member of this group, Yanigihara Kyokudō, established a haiku magazine, Hototogisu, an allusion to Shiki’s pen name. Operation of this magazine was quickly moved to Tokyo. Takahama Kyoshi, another disciple, assumed control and the magazine’s scope was extended to include prose work.

Although bedridden by 1897, Shiki’s disease worsened further around 1901. He developed Pott’s disease and began using morphine as a painkiller. By 1902 he may have been relying heavily on the drug. During this time Shiki wrote three autobiographical works. He died of tuberculosis in 1902 at age 34.

Shiki played baseball as a teenager and was inducted into the Japanese Baseball Hall of Fame in 2002. A group of 1898 tanka by him mention the sport.