He began painting down by Ruddiman Creek near his home in the early 1960s as well as by the shores of Lake Michigan and Lake Muskegon. Jack worked with oils and watercolors for many years, until the late nineties, when he began using acrylics to paint his 2-dimensional works of art.

In 1975, Jack moved to Fredericksburg, Virginia, and was well known as the curator of the Old Stone Warehouse, where he opened the famous Unknown Gallery in 1990. He continued painting on the shores of the Rappahannock River and hosted annual exhibitions where many of his paintings were sold to local residents. In 2020, Jack moved to Florida with his wife, Renee, and their white lab, Sofie.

Jack continues to paint using his own unique style by the shores of local lakes and rivers in Central Florida.