Through his friend Kawahigashi Hekigotō, he became acquainted with the renowned poet Masaoka Shiki and began to write haiku poems. In 1898 Takahama became the editor of Hototogisu, a magazine of haiku that was started by Shiki. He and Kawahigashi, the two outstanding disciples of Shiki, became pitted against each other after Shiki's death.

Kawahigashi became the leader of a new style of haiku, one that disregarded the traditional pattern. For a time Takahama was preoccupied with writing novels in a realistic, sketchlike style, but he eventually returned to haiku. Writing in Hototogisu, he opposed Kawahigashi's new movement and advocated realism in haiku, stressing that haiku poets should contemplate nature as it is. He published these beliefs in Susumu beki haiku no michi (1918; “The Proper Direction for Haiku”). His numerous collections of poetry have been compiled into the two-volume anthology Takahama Kyoshi zenhaiku shū (1980; “The Complete Haiku Poems of Takahama Kyoshi”). Takahama also wrote several novels, including Haikaishi (1909; “Haiku Poet”).