At the age of 25, Caldwell continued to be single, living with his parents in Forest Park, Cook County, and he joined his father as a broker in the Chicago Board of Trade.
By 1930, Caldwell married Marguerite Friedley, a public school teacher, has his own house in Proviso Township, Cook County and continued to work as a broker at the Chicago Board of Trade.
By 1940, the US census records list Caldwell as a freelance artist and his wife as a public school teacher.
The Caldwells had no children and remained in Cook County until Orval died on February 18, 1972, and Marguerite on April 13, 1976.
Art was a second career for Caldwell, who initially made his living as a commodities broker.