[3][4] Like many women journalists at the time, Winn started her career as a teacher, teaching both botany and chemistry in her native town of Ohio.

[3] Her desire to write, and a series of articles on botany, illustrated by one of the boy pupils in her class, was her introduction to newspaper work in the city of St.

[1][3] Winn was one of the founders of the Century Club of her native town — Chillicothe, Ohio — one of the others who was a charter member being Mrs. Wilson Woodrow, well known in literature.

[3][1] Winn was the representative of her newspaper on the Board of Lady Managers for the Louisiana Purchase Exposition in 1904, and counted as one of her privileges to have met Cardinal Francesco Satolli, among others.

Introduced to him by Archbishop John J. Glennon as a newspaper writer, he impulsively picked up a menu at a dinner in his honor at the German House, and wrote down "Honestas, Veritas, Caritas", saying, "Let this be your motto: 'Be honest always in what you write, tell only the truth, and love your profession so dearly that you will never fall short of your ideal of perfect fairness.'

[7] As early as 1903, she was recognized as a journalist to whom even men paid their homage: The Journalist, a New York City weekly periodical devoted to the interests of newspaper people and their work, profiled Winn in its series of prominent writers: "Among the feminist contingent of the Globe-Democrat's staff, a lady whose work is attracting particular attention, is Miss Jane Frances Winn, who writes of women's clubs, golf, whist, botany and kindred subjects.

Under the pen name of "Frank Fair" her brilliant articles are widely read, as well as are her clever contributions each week in the magazine section.

[4][9] In 1905, she wrote "Elsinore, or the Land of the Silver Lining", which was represented by child actors at the Century Theater in St. Louis under the direction of Jacob Mahler.

[16] In 1921, Winn, speaking on free verse as a "protest against old-fashioned rhymes", called Walt Whitman the "father of the new movement" and Sara Teasdale the "Shelley of America".