While Shiga was at the Gakushuin he became friends with Saneatsu Mushanokōji and Kinoshita Rigen.
His literary career began with a handwritten literary magazine Boya ("Perspective"), which was circulated within their literary group at the school.
In 1910 Shiga contributed the story Abashiri made ("To Abashiri") to the first issue of the literary magazine Shirakaba, which he helped to create.

To the dismay of his family, Shiga announced his intention to become a professional writer.
In 1912, he published Otsu Junkichi, a thinly-veiled autobiography of his affair with the family maid.
The family was so scandalized by the novella that Shiga was forced to move out of the family home.
The work was also a forerunner of Shiga's adherence to the indigenous I Novel literary form, which uses the author's subjective recollection of his own experiences.

During this period, Shiga established his reputation as a writer of short stories, including Kamisori ("The Razor", 1910), Seibei to hyotan ("Seibei's Gourd", 1913) and Manazuru (1920).

After Shiga married the cousin of Saneatsu Mushanokōji, who was a widow already with a child, in 1914, the break in relations with his father became complete, and he renounced his inheritance.
However, after the birth of his second daughter in 1917, he was reconciled with his father, and related the story in his novel Wakai ("Reconciliation", 1917).
This was followed by his major work, An'ya Koro (A Dark Night's Passing, 1921–1937), which was serialized in the socialist magazine Kaizō.

Shiga's terse style influenced many later writers, and was praised by Ryūnosuke Akutagawa and Agawa Hiroyuki.
However, other contemporaries, notably Dazai Osamu, were strongly critical of this "sincere" style.

During his lifetime Shiga moved house an estimated 28 times in various locations around Japan.
 He wrote stories connected with most of the places he lived in, including Kinosaki ni te ("At Kinosaki") and Sasaki no baai ("In the case of Sasaki").
One of his longer stays was in Nara, where he lived in a house facing Nara Park from 1925–1938.
Due to frequent visitors from the literary world, the house was dubbed the "Takabatake Salon" from the name of its neighborhood.
The house has been preserved, and is open to the public as a memorial museum.
After Nara, Shiga moved to Kamakura, and from there he moved to the hot spring resort town of Atami, Shizuoka from the war years onwards.
Frequent visitors to his house included the writer Hirotsu Kazuo and the film director Yasujirō Ozu.
While Shiga was at the Gakushuin he became friends with Saneatsu Mushanokōji and Kinoshita Rigen. His literary career began with a handwritten literary magazine Boya ("Perspective"), which was circulated within their literary group at the school. In 1910 Shiga contributed the story Abashiri made ("To Abashiri") to the first issue of the literary magazine Shirakaba, which he helped to create.
To the dismay of his family, Shiga announced his intention to become a professional writer. In 1912, he published Otsu Junkichi, a thinly-veiled autobiography of his affair with the family maid. The family was so scandalized by the novella that Shiga was forced to move out of the family home. The work was also a forerunner of Shiga's adherence to the indigenous I Novel literary form, which uses the author's subjective recollection of his own experiences.
During this period, Shiga established his reputation as a writer of short stories, including Kamisori ("The Razor", 1910), Seibei to hyotan ("Seibei's Gourd", 1913) and Manazuru (1920).
After Shiga married the cousin of Saneatsu Mushanokōji, who was a widow already with a child, in 1914, the break in relations with his father became complete, and he renounced his inheritance. However, after the birth of his second daughter in 1917, he was reconciled with his father, and related the story in his novel Wakai ("Reconciliation", 1917). This was followed by his major work, An'ya Koro (A Dark Night's Passing, 1921–1937), which was serialized in the socialist magazine Kaizō.
Shiga's terse style influenced many later writers, and was praised by Ryūnosuke Akutagawa and Agawa Hiroyuki. However, other contemporaries, notably Dazai Osamu, were strongly critical of this "sincere" style.
During his lifetime Shiga moved house an estimated 28 times in various locations around Japan.  He wrote stories connected with most of the places he lived in, including Kinosaki ni te ("At Kinosaki") and Sasaki no baai ("In the case of Sasaki"). One of his longer stays was in Nara, where he lived in a house facing Nara Park from 1925–1938. Due to frequent visitors from the literary world, the house was dubbed the "Takabatake Salon" from the name of its neighborhood. The house has been preserved, and is open to the public as a memorial museum. After Nara, Shiga moved to Kamakura, and from there he moved to the hot spring resort town of Atami, Shizuoka from the war years onwards. Frequent visitors to his house included the writer Hirotsu Kazuo and the film director Yasujirō Ozu.
Naoya Shiga