As a child, Shiki learned Chinese poetry from his grandfather, Kanzan Ohhara, and developed his talent for literature. He naturally became involved in a Chinese poetry circle with his friends. He also became interested in politics and, at fifteen, was determined to become a politician. Later, he went to Tokyo, and while studying at the university, began writing a novel, Yamabuki no Hitoeda (A Spray of Japanese Roses) and a halkal (haiku) essay entitled Haiku Bunrui (Classifying Haiku). In 1892 he dropped out of university and joined the Nihon newspaper staff, thus beginning his career as a journalist on the basis of a haiku column for the "Nihon" newspaper. During this time, he completed a novel named Tsuki no Miyako (A Town in the Moon).

portrait of Shiki in his thirties

Around 1896, the literary revolution which Shiki had been helping to promote achieved success in the fields of haiku, modern style poetry, tanka and sketch poetry. Confined to bed, Shiki devoted himself to his creative activity and completed writing a number of essays, such as Bokujuu Itteki (A Drop of Chinese Ink) and Byosho Rokushaku (Six Feet in Bed), as well as some sketches in Gangu Cho (Sketch Book). In 1902, Shiki died at the age of thirty five.

Shiki Masaoka, who suffered from tuberculosis, began his service as a journalist during the Sino-Japanese War (18941895.) When his condition became critical he returned to his home town, Matsuyama, in order to rest where he stayed for about 50 days with one of his university friends, Soseki Natsume. Soseki later became one of the greatest novelists in Japan. At the time, he had been working for Matsuyama junior high school as an English teacher. The two writers enjoyed discussions about Japanese literature. Soseki was then developing his interest in the creation of literature and Shiki was engaged in writing an essay titled Introduction to Haikai, which offered a comprehensive analysis of the revolutionary movement in haiku.

Shiki Masaoka is remembered to this day as one of the greatest Japanese haiku poets, who contributed to the introduction of modern style and high literary quality as ingredients of Japanese traditional haiku poetry.

The Matsuyama Municipal Shiki Museum was constructed to keep alive the memory of Shiki Masaoka, the Father of modern Haiku poetry. The town of Matsuyama seems to possess a "mysterious creative power" that fosters literature and poetry and attracts authors and lovers of literature alike. Many eminent writers have also visited here for centuries. The Museum reflects Matsuyama's tradition and environment, both of which greatly influenced Shiki. It is the sanctuary of modern haiku.