Benjamin B. Olshin was born in the United States but spent much of his life abroad, immersing himself in various cultures and disciplines. His journey began with a university trip to Sri Lanka, followed by studies in archaeology and history in Italy. He attended the Rhode Island School of Design program in Rome, where he honed his skills in watercolor painting and drawing. After graduating from Williams College, Benjamin taught watercolor painting, calligraphy, and crafts in Surrey, England. His artistic pursuits took him to Portugal, where his work was exhibited by the American Cultural Center in Lisbon. He later returned to Portugal on a Fulbright grant, studying abstract sculpture and design while conducting research in the history of cartography. His academic journey culminated with an M.A. and Ph.D. from the University of Toronto, focusing on the history of cartography. Benjamin's diverse experiences have shaped his artistic vision, blending traditional techniques with digital media to explore themes of travel, culture, and the philosophy of landscape.