"Gladly Wolde He Lerne" is a short story written by Harry Turtledove. It was originally published in Analog Magazine in January 1991, and reprinted in the Turtledove collection Departures in 1993.
The story depicts the efforts of Ted Collins, over the years, to improve himself from the district school level to principal and finally to the pinnacle of his profession: classroom teacher.
Although the story appears to be science fiction, the only difference its world has from the one we live in is that the educational system is set up a bit differently.
The title is in Medieval English, and comes from Prologue, Line 310 of The Canterbury Tales by Geoffrey Chaucer.