Caillin studied art, and illustration at Sheridan College and animation at Algonquin College. Returning to his hometown of Hamilton Ontario in 2009, Caillin continued to practice his art while starting an apprenticeship as a goldsmith. He currently resides in the art district of James St. N. with his dog Max.

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Most recently Caillin's work has focused on the interplay of art, architecture and sense of place. In his continuing series of paintings "I'm so lost and I live just around the corner" Caillin borrows a line from local band the Arkells, as the inspiration to explore the lines of urban architecture and hidden places in the city he calls home.