Shiki was born in Matsuyama on September 17, 1867 to Tsunenao, a low ranking samurai and Yae the daughter of Oharo Kanzan, a teacher at the feudal clan school. His real name was Tsunenori, but he was called Noboru as a child. Shiki, lost his father at the age of five and Kanzan took over his education and educated him in the Chinese Classics. He was very strict and conservative. Shiki was also influenced by his uncle , Kato Takusen, who later served as a diplomat and the mayor of Matsuyama.

Shiki was inspired by the Freedom and People's Right Movement, and in 1883 he went to Tokyo to become a politician, but while studying at the Imperial University, his interest in politics and philosophy gave way to a growing fascination with literature. He began writing fiction, but he gradually concentrated on the study and composition of haiku.

When he was twenty-two, he began coughing up blood and adopted the pen name Shiki, the name of a bird that, according to legend, coughs blood as it sings. He decided to devote himself to literature, withdrew from the university, and began working for the newspaper Nippon.

Shiki called for the reform of haiku and tanka, very brief forms of traditional poetry of seventeen and thirty-one syllables, respectively. Haiku, in particular, focus on nature and or simple occurrences of daily life, but the condensation required by the form can result in great expansiveness and depth. The traditional forms, however, had grown trite and formulaic over the years. Shiki recommended composition based on Shasei, or sketch from life, and interjected this principle of describing life just as it is into his prose writing, as well as his haiku and tanka. Until two days before his death, Shiki continued writing articles, including a series under the title Byo-sho Rokusyaku (A Six feet Sickbed), in spite of intense suffering from the spinal caries that had afflicted him since 1895. He died on September 19,1902.

During his brief life, Shiki attracted a number of followers, who were influenced by and carried on his sketch-from-life theory of literature. Through them, as well as in his own right, he left his mark on the history of modern Japanese literature.

Poems by Masaoki Shiki

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There was the day we swam in a river, a lake, and an ocean.
And the day I quit the job my father got me.
And the day I stood outside a door,
and listened to my girlfriend making love
to someone obviously not me, inside,