Those children are grown now, and Whitehead, 48, owns 100 valuable but long-dormant acres in central Missouri. Like her father before her, she hopes to cultivate that acreage to help pay for her eventual retirement.
Working a combine was no problem for Whitehead, one of five daughters who grew up on a 1,000-acre Montgomery County farm her father still owns. But with little understanding of the business side of agriculture, Whitehead was lost when she asked a local banker for a farm loan.
The banker's response only made matters worse.
"Bring your dad with you next time," he told her.
"It was very intimidating," said Whitehead, who also works full time as a project manager for the local conservation district.
Nearly 40 miles south of Whitehead's farm, stories like that evince knowing nods and similar tales among the dozen women gathered in a Fulton classroom for the latest session of Annie's Project, a farm management training program started in Illinois four years ago.
The project has since grown to seven other states, including Iowa, Nebraska, Wisconsin, North Dakota, Minnesota and Missouri, said founder Ruth Hambleton, a University of Illinois extension agent. The program is named after her late mother, Annette Fleck.
Encounters such as the one described by Whitehead are all too common in what remains a male-dominated line of work, Hambleton said.
"One of the things women tell us is the worst teacher they have is the man they're married to," said Hambleton, who is based in Mount Vernon, Ill. "Sometimes when you ask questions, especially when you married into a [farm] family, you're looked at with suspicion."
Participants in the program -- started with the help of a U.S. Department of Agriculture grant and which Hambleton hopes to expand nationwide -- are farm wives, farm widows, divorced farmers such as Whitehead, and the occasional single female farmer.
More than just managing spreadsheets, understanding crop insurance and mastering market plans, the six-week program extols the virtues of strength in numbers, said Karisha Devlin, a University of Missouri extension agent in Shelbyville.
"Women, once they share what's going on in their lives, they see they're not the only one faced with this situation," said Devlin, who is also married to a farmer.
Bonds forged in the Annie's Project classroom continue long after the formal lessons end, said Hambleton.
Missouri classes began last year in Kirksville, Hannibal and Mexico, with another round now underway in Bethany, Carrollton, Fulton, Hermitage, Mountain Grove, Neosho, Nevada and Savannah.
For Whitehead, the pain of that meeting with the insulting banker remains fresh. She eventually got the farm loan from another lender and has made modest progress clearing brush and repairing erosion damage on the fallow land she admittedly neglected to raise a family.
Each week, she drives 75 miles round-trip to attend the Annie's Project class after working all day.
Married at 19 and divorced by 33, the grandmother of three is looking for hard facts -- and a dose of confidence to make it alone in a world she has mostly witnessed from afar as a child.
"Our biggest role was to help get the meals on the table," she recalled. "It's been a challenge. Before, I didn't make a lot of decisions. I was the helper. Now I find myself second-guessing myself a lot."
Hambleton, whose own mother juggled family and financial hardship but ultimately died wealthy, called the program's popularity a mixed blessing.
"I sorely underestimated the demand for this program," she said. "Nobody has paid attention to that kind of need."
On the Web: www.extension.iastate.edu/annie