Asa Jackson was born between 1795 and 1800 in Loudoun County, Virginia to Eura (Newhouse) and John Jackson. He lived in Loudoun County for his whole life, spending most of his time in the Southern District, in the areas around Mountville and Middleburg. He married Susan Rhodes, also of Loudoun County, and had nine children. Jackson died on July 6, 1866 and was buried in Union Cemetery in Leesburg.

Jackson made a living in a variety of ways. He held a position in the Goose Creek and Little River Navigation Company in 1839. The incorporated company attempted to make Goose Creek and the Little River, both major waterways in Loudoun County, useful as highways. Jackson also owned interest in a mill on Goose Creek near Snickersville Turnpike and Mountville, and registered a patent on a machine for winnowing grain in 1841. He is listed as a millwright in the 1850 census. Jackson's primary source of occupation over the years, however, was as surveyor. As an independent surveyor, he regularly surveyed parcels involved in land transactions. He also worked as a Commissioner in Chancery for the Chancery Court of Loudoun County. A commissioner could be appointed to relieve the court of dealing with the more complicated and technical details involved in the settling of cases. Jackson would survey land in dispute or parcels of land to be divided among heirs for the court, for instance. He then submitted copies of the completed surveys to the court or to the individuals who requested the surveys, and collected his fees. Jackson maintained clean copies of his surveys in personal survey books. These books contain the descriptions of parcels of land in Loudoun County, but contain few plats or drawings.

As one of the original thirteen colonies, Virginia's land was not surveyed in accordance with the Public Land Survey System. That system is a mathematically designed system of surveying, and has been in place in the United States since the passage of the Land Ordinance of 1785. Virginia was originally surveyed using the British system of metes and bounds, or descriptions of property lines based on markers. The markers were often topographical, but could be natural, manmade, or created specifically for the purpose of marking a boundary.