When his father died early, Kristian moved with his mother back to Prestgard, her family neighboring farm.
After two years at the Askov Højskole in Jutland, Denmark (1886–88), he started teaching at the folk high school operated by Johan Christian Viggo Ullmann in Seljord.
As consequence, Prestgard was offered a job in Arvesen's newspaper, Oplandenes Avis, which began his career as a journalist.
In 1897, he married Oline Musum (1873–1919) and took a position with a Norwegian language newspaper company in La Crosse, Wisconsin.
Probably the most widely known of these work was En Sommer i Norge, his account of a journey to Norway with a group of American journalists during 1927.