Dillard began with the simple step of shaking hands with blacks and also forming relationships with white teachers who taught black children (both were taboo subjects). He would eventually take on the role of directing the two funds mentioned in the overview. He also became involved with many other initiatives promoting education for African Americans (see the links for more information). He moved to Charlottesville, Virginia in the 1930s and died in his sleep in 1940. He continued to be involved in his educational pursuits for black education during these last years.