Olesen was born in Cordova Township, Le Sueur County, Minnesota to Peter Daniel and Margaret Jones Dickie.

[2] Olesen became a travelling Chautauqua speaker to support her family's income, through which she gained national attention.

[2] The acquaintances she gained included William Jennings Bryan, who was a supporter of the women's suffrage movement and of Olesen's involvement in politics.

[1] Olesen became known as an effective orator, and in 1920 she became the first woman to speak at the Democrats' Jackson Day dinner, which furthered her popularity as a speaker.

[2] Olesen's first foray into politics beyond her speaking ventures came in June 1920 when she became a delegate to the Democratic National Convention.

[3] Her competitors for the general election included Henrik Shipstead, nominated by the Farmer-Labor party and Frank B. Kellogg, the incumbent Republican.

[1] In 1923 she moved to Northfield, Minnesota so that Peter could take on a job at Carleton College as a registrar and German professor.