dudley worked as a teacher. he first taught in a first-grade classroom in sampson county. the following year he became principal of peabody graded school in wilmington, north carolina in 1881. the school at this time was one of a few "very good public schools for african americans" in the area. he spent the next 15 years teaching in wilmington. he was also president of the state teachers' association for negroes for six years.