Wain soon quit his teaching position to become a freelance artist. In this role, he achieved great success. He specialized in drawing animals and country scenes, and worked for several journals including the "Illustrated Sporting and Dramatic News", where he stayed for four years, and "The Illustrated London News", beginning in 1886. Through the 1880s, Wain's work included detailed illustrations of English country houses and estates, along with livestock he was commissioned to draw at agricultural shows. His work at this time includes a wide variety of animals, and he maintained his ability to draw creatures of all kinds throughout his lifetime. At one point, he hoped to make a living by drawing dog portraits.