Partnering first with his own father, James and Abel spent the summer of 1849 driving sheep to Indiana to sell at market.

The following year, James drove another flock to Danville, Illinois, pasturing them briefly and selling the herd at a larger profit.

His educational interests continued briefly during the winter of 1850 in Wabash College at Crawfordsville, IN before he resumed his sheep herding enterprises.

It is unclear when James Millikin formally met Anna Bernice Aston, the daughter of Rev.

A legend, according to Dr. Albert Reynolds Taylor, first president of Millikin University, was James' sisters wrote to him encouraging the relationship.

While recognized quickly as a safe and stable institution, the Millikin bank made little money and keeping his own $75,000 fortune intact during those years was a priority.

Following their marriage, James and Anna Millikin briefly lived at the Revere House, a prominent Decatur hotel until purchasing a small home at the corner of Edward and William Street they affectionately recalled as "the cottage."

A new kitchen was added to the northwest corner of the house so a new grand staircase could be placed adjacent to the north parlor room.

In later years, James and Anna Millikin travelled frequently to Europe and purchased artwork for the home.