Handy taught school at Damos Quarter, in Somerset County, Maryland, and in 1881, at the age of 19, was selected to be principal of the high school at Smyrna, Delaware. By 1887 he was superintendent of all the public schools in Kent County, Delaware, and by 1890 he had been hired as principal of Old Newark Academy, in Newark, Delaware. Meanwhile, he was studying the law with John R. Nicholson of Dover, Delaware and frequently speaking at teacher's training schools in the region.