From 1897 to 1907, he worked as a reporter, telegraph editor, assistant city editor and literary editor for the Minneapolis Journal. From 1907 to 1913, Kirkwood freelanced as a magazine writer. In 1914, he joined the University of Minnesota staff as director of publications, working in that position until he retired January 1, 1936. In 1922, he received a master's degree in journalism from the University of Missouri.

While at the university, he organized and taught the first journalism courses there in 1915. These courses led to the establishment of the university's School of Journalism and Mass Communications. He also started the university's printing department, initiated a radio broadcasting service and started a long tradition of short courses for weekly newspaper editors in cooperation with the Minnesota Newspaper Association.

In 1928, while on a sabbatical leave from the University of Minnesota, he started a newspaper in Waynesboro, Virginia and ran it for a year to gain practical editorial experience.

When Kirkwood retired from the University of Minnesota in 1936, he was named professor emeritus of agriculture and journalism. Following retirement, he wrote his autobiography, "The Memoirs of Homo Sap," published in 1956. He died April 9, 1957, at the age of 90 in St. Paul, Minnesota.

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