In 1896, he held a joint exhibition, with Isaac Levitan and Alexander Popov [ru], in Odessa.
In 1898, he decided to devote his career to working with the newly founded Moscow Art Theatre, where he would create designs for fifty-one performances and earn the admiration of the iconic actor, Konstantin Stanislavski.
[1] Simov not only created a new aesthetic for set design, he was also involved with ideological interpretations of the material, and the directing process.
[1] In 1924, he designed sets depicting Mars, for the groundbreaking science-fiction film, Aelita, by Yakov Protazanov.
The following year, he also served as an artist, under the direction of Ivan Stepanov, for The Stationmaster, a dramatic film based on a story by Alexander Pushkin.