In 1919 Hennacy married his first wife, Selma Melms, under Common law. In May 1920, Hennacy graduated from the socialist Rand School of Social Science. In 1921, Hennacy and Melms hiked around the United States passing through all 48 of the contiguous states. He settled down in 1925, buying a farm and raising his two children. In 1931, he began social work in Milwaukee and organised one of the first social worker unions. He refused to use force or self-defense even when threatened during his work, preferring instead to use nonresistance. During this time, he also refused to sign up for the draft for World War II and declared that he would not pay taxes. He also reduced his tax liability by taking up a lifestyle of simple living. Between 1942 and 1953, Hennacy worked as a migrant farm labourer in the southwest United States.