One of the most important occupations or jobs in the community was the delivery of the next generation. The job that Mrs. Carrie Bush did was midwife for the delivery of precious boys and girls.
Farming was the main livelihood of the earlier families. Some lived on farms owned by the Caucasians and worked the farms for them until they became able to purchase their own farms. When they purchased their own farms, some of the crops that they raised were peanuts, cotton and grains to feed their livestock. Since the Oakland-Chuckatuck community is surrounded by water, many became oystermen.
As time passed, farming became less popular as a means to support a family. Many men went into the United States Military, thus getting worldwide experience in other states and countries. After they returned, there were other jobs to be had at various businesses including Kirk Lumber, Lone Star Marl Company, Planters Peanuts, Lummis, Birdsong Peanut, Newport News Shipyard, Webster Brickyard, W. G. Saunders Lumber Company, Chuckatuck Ice Plant.
By this time women had begun to work. They worked as domestics, some traveled north to New York, Connecticut, New Jersey, and other places to seek employment. Many of the mothers and their children worked on the truck farms harvesting white potatoes, string beans, strawberries, other produce and picking flowers. The older responsible children and teens chopped grass out of the peanuts in large fields.
Some became contractors, brick masons, electricians. Some of the men became longshoremen.
Entrepreneurs George Walker opened a community grocery store. Harvey Wilson learned how to lay bricks and taught his brothers and they taught their sons. Horace Brown had a community barbershop. He passed the trade on to his sons, Lafayette and Glenn. Earnestine Cowling Brown and Annie J Boothe each had a home based business:they were Hair Dressers. McKenzie Roberts Wilson had her own Hair Dresser Shop; Carrie Jackson Hall was one of the community seamstresses.