When he was twelve years old, Shishkin was enrolled at the Kazan Grammar school, where he soon would find friends which he could discuss art and draw with. Shishkin was an avid student of natural sciences.

Shishkin never came back to the grammar school after the summer holidays of 1848. To him, the school's setup was an obstacle to his intentions and aspirations with its "narrow-minded formalism."

Later, Shishkin studied at the Moscow School of Painting and Sculpture, under the teachings of Apollon Mokritsky, who gave Shishkin a solid foundation to build his bright future as an artist. At that time, the artist often drew in the woods near Moscow.

Shishkin studied at the St. Petersburg Academy of Arts from 1856 to 1860, under the guidance of Maksim Vorobyev. Upon his admission to the Academy, Shishkin's former teacher express that he lost a talented, excellent pupil. Still, he was hopeful that he would become an outstanding artist if he maintained the same passion he has shown before. Mokritsky's expectations of Shishkin were right. Shishkin would be warded silver and gold medals during his time at the Academy.

Shishkin's first travel abroad was in 1862 when he went to Dresden and Berlin. However, he wasn't very impressed and felt slightly homesick. However, he sparkled in Prague, impressed by the artwork of realist Czech painter Josef Manes and his Slavonic types.

Shishkin learned the technique of etching during his time in Zurich, with Sir Robert Collier. Shishkin would also become a master of etching and lithography.

Shishkin returned to Russia in 1865, when he received the title of academician for his painting View Near Dusseldorf. He soon was amongst the most distinguished of the capital's artistic circles.

Shishkin was a member of the Peredvizhniki, or The Itinerants, a group of Russian Realist artists, in protest against narrow-minded academic restrictions. He was considered one of the most distinguished artists in the group. Shishkin exhibited with The Itinerants until the rest of his life.

Shishkin had a rather tragic personal life. He married twice, and he became a widow both times, all his sons died as well. However, those tragic moments never appeared through his artwork.

Shishkin produced one of his most exquisite works in 1898, Ship Timber Grove, which was his very last painting.

Ivan Ivanovich Shishkin died suddenly in his studio in March 1898.