Benson opened his first studio in Salem in 1886 with his friend, Phillip Little, and began painting portraits, an occupation in which Benson took seriously. He once said: "The more a painter knows about his subject, the more he studies and understands it, the more the true nature of it is perceived by whoever looks at it, even though it is extremely subtle and not easy to see or understand. A painter must search deeply into the aspects of a subject, must know and understand it thoroughly before he can represent it well."