Anton Chekhov’s brother Ivan was only a year younger than the writer. When their father went bankrupt and the family left Taganrog, Ivan and Anton stayed behind to look after the house and finish grammar school. The boys were 15 and 16 years old. There was not enough money to pay tuition, and, having completed only five grades of grammar school, Ivan moved to Moscow to live with his parents.

In Moscow, Ivan decided to become a teacher; he studied on his own and passed the exam at the age of 19. After receiving a government apartment, he began to teach in the city parish school of Voskresensk — today the city of Istra in the Moscow region. ere he received his first commendation from the Zvenigorod School Board for excellent teaching. Later Ivan Pavlovich was awarded various distinctions: a medal in memory of the deceased Emperor Alexander III, a silver medal to be worn in the buttonhole on Andrew’s ribbon in memory of the coronation of Emperor Nicholas II, a medal of the school, established by the merchant society in memory of the majority of Tsesarevich Alexander Nikolayevich.

Every time Ivan Chekhov received an assignment to a new school, he would relocate and arrange his classroom in his own way, doing repairs and mending books in the library, binding them himself. Ivan Pavlovich loved to keep things in order, a trait he probably inherited from his father, Pavel Yegorovich.

In April 1886 Anton Chekhov wrote:

It was at the time that Ivan Pavlovich was assigned to the Arbatsky Government School, where he served for less than a year.

Ivan Pavlovich met his future wife, Sofia Vladimirovna Andreeva, while working at the city elementary school. They got married on July 9, 1893, in Melikhovo, and a year later their son Volodya was born.

His former pupils loved Ivan Pavlovich very much and sent him poems, cards and congratulations all the time; they brought their children for him to teach them. Ivan Pavlovich staged plays with his students, and newspapers reported on them; he talked a lot with children and respected them. At the age of 44 Ivan Chekhov was awarded the highest title of hereditary honorary citizen of Moscow for his contribution to public education.