Armstrong was born in McDuffie County, Georgia. He attended school until eighth grade when he left and began working in the local cotton fields. He married Ulamay Demmons in 1929 and had two daughters. For much of his life, he worked picking cotton on the local Mack McCormick farm. He supplemented this income by building furniture for people in his community. One of the things Armstrong was most skilled at building were wooden and concrete vaults, which were especially popular in rural communities because of a distrust of banks in the aftermath of the Great Depression. These vaults often incorporated a wide variety of types of locks, handles, and wheels. After his wife died in 1969, he began to work at the Thomson Box Factory, staying there until 1982. Religion was a significant part of Armstrong’s life. He was a member of The Solomon Hodges Burial Society, an organization that helped the poor pay for proper burials for family members who had passed.

These calendars were built in Armstrong’s hand-built two room home. While one room served as his living space, the other room served as his workspace. In that space, he kept not only the calendars and the materials for building the calendars but also many other things that he had built himself. One of the major features of the room was a large box that Armstrong kept on his mantelpiece that held the cards that Armstrong would use to help decide what dates to put on the calendars.