After joining a revolutionary student organization, he was arrested in December 1901 and exiled to Amga in the Yakutsk region of Siberia.
In 1904 Chulkov moved to St. Petersburg and became the de facto editor of Novy Put' (New Path), a literary magazine published by Dmitry Merezhkovsky and Zinaida Gippius.
When the publication of Novy Put' was suspended in January 1905 during the turmoil of the Russian Revolution of 1905, Chulkov moved to Voprosy Zhizni (Problems of Life), its replacement, where he worked with its editors Nikolai Berdyaev, Sergei Bulgakov and Nikolai Lossky until it folded in December 1905.
Russian poets Alexander Blok and especially Vyacheslav Ivanov were supportive of the new movement while Valery Bryusov, the editor of the leading Symbolist magazine Vesy (The Balance), and Andrei Bely were opposed to it.
Chulkov published a number of novels, poems and short story collections between 1906 and the outbreak of World War I in 1914, when he joined the Russian army.