In 1828, the family moved to the “boomtown” of Monroe, Michigan, following the death of Charles. In Monroe, John Dean found considerable success working as a housepainter and a carpenter. This success allowed him to support his family and educate his children. During their childhood, Robert and his four brothers apprenticed in the family trades of house painting and carpentry. While Robert's brothers achieved modest success as housepainters, Robert emerged as the most talented of his siblings in his apprenticeships. In 1838, Robert established a painting business with partner John Gamblin. Robert and his partner frequently advertised their services in local publications, like the "Monroe Gazette". However, in 1839, Robert suspended the business in order to pursue his ambition to work as a portrait painter.