In "The Legend of Sleepy Hollow" by Washington Irving, Ichabod Crane is the local schoomaster:

truth to say, he was a conscientious man, and ever bore in mind the golden maxim, 'Spare the rod and spoil the child.'--Ichabod Crane's scholars certainly were not spoiled.

When school hours were over, he spent time with his students and was boarded in the homes of some of his students.  To earn money, he helps the farmers in the "lighter labors" of their farms; he works during hay season, mends fences, waters the horses, drives the cows from the pasture, and cuts wood for the winter fire--all tasks that an older boy can do.  Sometimes Ichabod would even babysit, holding a child on his knee or rock a cradle with his foot for hours.  In addition to these small tasks, he is the "singing-master" of the neighborhood, and earns many shillings by teaching the young people in "psalmody."  As the narrator humorously remarks, Ichabod Crane gets by 

in that ingenious way which is commonly denominated 'by hook and by crook.'

As a respected member of the community, the schoolmaster is also able to ingratiate himself with the "country damsels" as he gathered with them in the churchyard on Sundays, gathers grapes with them, and recites for them the epitaphs on the tombstones.  Because he spends so much time with different people, Ichabod is known as a "traveling gazette," who passes on gossip and news.  With the old Dutch wives, Ichabod spends long hours exchanging tales for Cotton Mather's History of New England Witchcraft.  The old wives, in turn, pass on their own tales.

What are Ichabod Crane's jobs in The Legend of Sleepy Hollow?

Ichabod Crane is the schoolmaster for the children in the vicinity of Sleepy Hollow. Sometimes he is referred to as a "pedagogue," which is just a fancy way of saying "teacher." He presides over the one-room schoolhouse where he runs a tight ship. Someone listening outside the schoolhouse would hear Crane's menacing or commanding voice as he taught or might hear the "birch" being applied to the body of a non-compliant student. Crane is not averse to using the rod on his pupils, following that old proverb, "Spare the rod and spoil the child." However, he is not overly mean to his charges; he befriends some of the older boys, especially if they have good-looking older sisters. He ingratiates himself with the parents of the schoolchildren so that he will be invited to dinner, thereby saving himself the expense of having to purchase his own food.

Crane's other source of income is providing singing lessons for the community. He gives group choir lessons to the young people who then sing during services at the church. His role as singing master gives him the opportunity to meet Katrina Van Tassel, the only daughter of the wealthiest landowner in the region. Katrina attends the music lessons one evening a week with the others, but soon Crane contrives to give her private lessons at her home, allowing him to survey the domain that he intends to inherit via marriage to Katrina.