At the time of his son James Wilson Jr.’s birth, he was working at the St. Charles Condensed Milk Company. Around 1896 he bought a part interest in a creamery in Romeoville, Illinois. By 1900 he sold his interest out, and moved to Aurora, Illinois where he worked for the Western Wheel Scraper Company. In 1901 he harvested fields in North Dakota, after which he took up a homestead of half breed script in Saskatchewan, and he summoned his wife and family by letter at that time. They left October 31, 1901, heading to Saskatoon.

The family lived in Romeoville, Illinois in the 1900 USA census.

In the 1911 census, there are two other people staying with them in the household. It also mentions that the family (except the youngest, Alma) were born in the USA and immigrated to Canada in 1901.