He was named after his grandfather on his mother's side, Gleb Fomich Sokolov who served as the head of the Office of State Property in Tula (up until 1848) and Kaluga (from 1848 onwards).

In 1853 Gleb entered the Tula gymnasium where he excelled, "his name never leaving the so-called 'golden desk' there", according to a fellow student's memoirs.

While studying in the local gymnasium, Uspensky devoted much of his time to reading the Russian classics and participated in the school's literary almanac "Young Stems".

[2] In 1866 he published a series of sketches about life in the suburbs of his native city of Tula under the title Manners of Rasteryayeva Street, which established his reputation.

In May 1867, having passed the special qualification exams in the Saint Petersburg University, he departed to the town of Epifan in the Tula Governorate and started working there as a teacher.

In 1874 the "Very Small Man" (Очень маленький человек) novella's two parts appeared in Otechestvennye Zapiski, but the publication stopped: the May issue of the magazine was withdrawn by censors.

[2] In the 1870s, as his financial position improved, Uspensky traveled widely, becoming acquainted with a number of revolutionary populists, such as Pyotr Lavrov (the Vperyod magazine's editor in London, who several months later published his essay "One Won't Hide a Needle in a Sack") and Sergey Stepnyak.

In April 1876 Uspensky re-joined his family in Paris, then in September went to Serbia, as part of the Russian volunteers' corps, to fight Turkey's occupation.

As a result, series of sketches "From the Country Diary", on local peasants' life there started being published in Otechestvennye Zapiski in October.

In 1882 "The Suspicious Beletazh" appeared in OZ (relating a bizarre incident involving a secret police agent's visit to Syabrintsy) as well as two more books, The Village Troubles (Vols.I-III) and The Power of the Land, arguably his best-known work, based on his studies of life in rural Novgorod region.

[1][2][6] In the spring of 1883 Gleb Uspensky travelled to the Russian South, visiting Tiflis, Baku and Lenkoran, meeting people from religious groups, fishing cartels and private oil enterprises, resulting with Notes from the Road.

[2] On April 20, 1884, Otechestvennye Zapiski were closed much to the distress of Uspensky who later gave the journal credit for helping him through hardships.

[2] In December 1886 Russky Vestnik started to publish another set of essays and sketches called "We: In Words, Dreams and Deeds", which impressed Vladimir Korolenko.

[2] Uspensky's book of essays Living Numbers (on the life of workers in the society of the rising capitalism) remained unfinished due to problems with censorship.

In December Works by Gleb Uspensky in two volumes was published by Pavlenkov, with Nikolai Mikhailovsky's foreword, and enjoyed commercial success.

He tried to substitute him as the head of the Internal affairs section in Russkaya Mysl, but the progressing illness made this impossible.

The famine in Povolzhje horrified Uspensky and prompted him to start what he called "the story of people's devastation" but his health was deteriorating too fast.

In March he still managed a trip to Povolzhje's worst hit regions and published reports in Russkaya Mysl and Helping the Hungry anthology.

[2] In September 1893 Uspensky informed V.M.Sobolevsky that he started writing memoirs about Turgenev, Saltykov, Vera Figner "and many other people who cared for the Russian land."

[2] Uspensky's works had a considerable influence on Russian literature and society, and were praised by many of his fellow writers, including Leo Tolstoy, Anton Chekhov, Maxim Gorky and Leon Trotsky.