Phillips was born in Springfield, Ohio. He was a personable, attractive young man and really had no interest or talent for clerking. He enrolled in Kenyon College in 1902 and found an audience for his art in the school year books. After his Junior year, he left Ohio for New York City, determined to earn a living with his art. J.A. Mitchell, the publisher
of Life Magazine, hired him at the age of 26. The association with the magazine endured throughout his life.