A native of Chicago, John was the artist in residence with the Around the Coyote Gallery in 2006. After receiving his BFA in painting from MIAD in 2010, Kowalczyk began his residency with RedLine Milwaukee where he holds a studio. He has participated in exhibitions at the Jackpot Gallery, Borg Ward Collective, American Fantasy Classics, the Sienna Art Institute in Italy, and the Charles Allis Art Museum, among others.

Kowalczyk participated in the Black Cat Alley project of 2016.