After the revolutions of 1917, Chertkov was instrumental in creating the United Council of Religious Communities and Groups, which eventually came to administer the Russian SFSR's conscientious objection program.

His mother (to whom he felt especially close), Elizaveta Ivanovna, born Countess Chernysheva-Kruglikova, was known among her circle in St. Petersburg society for her beauty, intellect, authoritativeness and tact.

In 1880, he resigned from military service, left Petersburg, and settled in his family's estate in Lizinovka, where he planned to help the peasants at whose expense he lived, although he had an unclear understanding of their needs.

Following Tolstoy's initiative, in 1885 Chertkov organized and financed a publishing house called Intermediary (Russian: Посредник) which specialized in the release of art and moralizing literature for people.

Intermediary succeeded in publishing works aimed at the education of the Russian people, despite the pressure of the Imperial censorship and the hostile attitude of the Eastern Orthodox Church.

Rossosh had a manor house on top of a hill, as well as an extensive courtyard and subsidiary buildings; at the base of this mountain were three ponds in succession, and behind them 20 desyatina of forest.

He was an avid Anglophile like his mother, admired the English tradition of free speech, and was already corresponding with a small collective based at Purleigh in Essex, who were looking to put Tolstoy's ideas into practice.

[3] It was to Purleigh, therefore, that Chertkov initially gravitated and it was here that he set up a publishing company, the Free Word Press (Russian: Свободное слово), producing Russian-language versions of Tolstoy's works and kindred literature, much of which was smuggled back into Russia.

Chertkov's wife, Anna Konstantinovna, born Dieterichs (1859–1927), was trustee of the Free Word Press and produced several texts for both arms of the business.

The Free Age Press continued to flourish, with a single member of the Tolstoy colony based at Tuckton House as translator and editor, until 1916.