[2] As a boy, he worked on his father's farm, peddled milk from the dairy, practiced orations behind the barn, and clerked in a hardware store.

He was admitted to the bar in 1899 and commenced practice in Algona, Iowa, Kossuth County in the north-central part of the state.

"[1] In 1918, Dickinson ran for Congress, challenging incumbent Frank P. Woods in the Republican primary for the seat in Iowa's 10th congressional district in north-central Iowa (made up of Boone, Calhoun, Carroll, Emmet, Greene, Hamilton, Humboldt, Hancock, Kossuth, Palo Alto, Pocahontas, Winnebago, and Webster counties).

Woods was then Chairman of the National Republican Congressional Committee, but had voted against the 1917 declaration of war on the German Empire,[3] creating a great political liability in 1918.

In 1932, he was chosen to deliver the keynote speech at the 1932 Republican National Convention, where fellow Iowa native Herbert Hoover was re-nominated for his failed re-election bid.

[1] In a 1934 speech, he argued that the only beneficiaries of the new Agricultural Adjustment Act were the "brain trusters" behind the new programs, sneering that, "taken from their dismal classrooms, chicken farms, editorial rooms and law offices, they now loiter behind mahogany desks solving problems of the world.

"[2] Time commented in 1936 that he "demands 'sane, honest industrial and agricultural programs' and a return 'to the ideas of our New England forefathers.

'"[1] In May 1936, Time reported that Dickinson was interested in the chance to run against President Roosevelt, speculating that "the buzzing in his large, well-shaped head" was the question, "'If Warren Harding could get the Republican Presidential nomination in 1920, why can't I get it in 1936?

For dark horse Dickinson, oldtime Harding supporters have been quietly conducting the same kind of preconvention campaign that Harry Daugherty put on for his Dark Horse in 1920—unobtrusively making friends, taking care not to offend leading candidates, building up a man on whom irreconcilably opposed factions could unite after a convention deadlock.

Meanwhile, in his race for re-election, Dickinson faced a strong primary challenge from a crowded field of other Republicans that included Brookhart.

After a strong battle in the Republican primary (in which he defeated U.S. Representative Lloyd Thurston), Dickinson again lost in the general election, this time by fewer than 3,000 votes.