By the time Jefferson was born in 1743, Virginia's tobacco planters had a long-established work regimen. Using a method adopted from Native Americans, enslaved field hands (able men and women over the age of sixteen) cut down trees or simply killed them by girdling the bark, and using hoes, planted tobacco seedlings among the stumps. When soil fertility declined after five to seven years, they abandoned the old field and cleared a new one. Enslaved laborers lived and worked together under the eye of an overseer.  They planted the seeds, transplanted the seedlings, weeded the fields, hoed the soil, and picked the leaves. They hung the leaves to dry, and in the winter, they stripped, sorted and prepared the leaves for market. As a gang, they performed the simple, repetitive, and physically demanding tasks of the seasonal cycle. This system simplified supervision of the work process; owners and overseers could accurately evaluate worker performance and administer physical punishments to force compliance.

For nearly the first twenty-five years of his ownership of the plantation, Jefferson follow this process, growing tobacco as Monticello's main cash crop. But during the turbulent years of the Revolution, Virginia's tobacco trade suffered, and, in its aftermath, faced increased foreign competition. Beleaguered planters saw an opportunity when, in the 1790s, conflict in Europe—the French Revolution and ensuing Napoleonic Wars—disrupted continental agriculture and commerce.

Many planters diversified into grain production, including Thomas Jefferson. In 1793 he wrote to George Washington "Good husbandry with us consists in abandoning Indian corn and tobacco, tending small grain, some red clover following, and endeavoring to have, while the lands are at rest, a spontaneous cover of white clover." He sent his first harvest of wheat to market that year, and it remained the primary export crop at Monticello until his death in 1826.

Jefferson's practice of "Good husbrandy" transformed the Monticello landscape and its plantation community, but its effects were not felt at his western farms, such as Poplar Forest, where he continued to grow tobacco.