"we may go together to fulfil my part of the prophecy up on Mount Holyoke"

After graduation, Caroline taught high school English and Latin for six years in Iowa, her home state. In 1907 she joined her parents who had moved to Oklahoma. There she began a teaching position at Center School, near a settlement now known as Eva, and established a claim on a section of land across the road from the school. 

In this letter from spring 1908, Caroline tells Rose of her plans to marry Mr. W.E. Henderson in May. "Someday," she writes, "we may go together to fulfil my part of the prophecy up on Mount Holyoke in 1901, for that located me on a western ranch." In fact Caroline and her husband Wilhelmine (Will) would reside on their land in Oklahoma until 1966, up until the end of their lives.

Caroline met Will when he helped to dig a well on her claim. "[Y]ou could not help but realize that he is an optimist of the sincerest sort," she writes to her friend, "ready to do all his part to make things come right with a faith above and beyond his own effort. I think sometimes it will worry me because he simply won't worry over anything, but that is a pretty good failing after all."