New England is made up of six states: Connecticut, Massachusetts, New Hampshire, Vermont, Rhode Island, and Maine. If Willy Loman is the company's "New England man" and covers that vast territory all by himself, it is certainly understandable that he could be worn out after so many years on the road. In 1949 when the play was produced, many of the highways in those states were only narrow strips of black asphalt with a white line down the middle. That is, there was one lane going in each direction. In order to pass another car the driver had to look for a chance to turn out into the lane for the oncoming traffic. Many of the roads must have been winding, so that passing a slow-moving truck was taking a gamble. When Lyndon Johnson was president he inaugurated a system of nationwide divided highways, making driving much safer and easier; but that wasn't until the late 1960s. Imagine driving from New York City to Maine and back again on those primitive highways in states which have rugged mountains and terrible weather in the winter. The driving distance from New York to Maine is about four hundred miles. No doubt Willy would make stops in other states. He would be driving around 1500 miles a week in an old car. He might have an AM radio in the car, but there would be little to listen to after he left New York City. Since Willy could only do business on weekdays, he would have to return home late on Friday after driving for several hours in the dark. He would spend Monday, Tuesday, Wednesday, and Thursday nights in hotel rooms. There weren't many motels in those days. The name "motel" was virtually unknown until after World War II, which ended in 1945. According to the enotes study guide (see reference link below), Willy is already sixty-three. That sounds like a killer job. No wonder he was thinking about suicide! Driving alone and spending most of his nights alone in cheap hotel rooms would lead to morbid thoughts as well as to drinking.
Well, I am not too sure that we are given that much information about Willy's job in the play except that it is something that is bound up as part of Willy's identity and that it means everything to him. He overtly says that he loves his job and that he lives for it, yet clearly, as the opening scene demonstrates, other characters such as Linda recognise that his job is too much for Willy to cope with and that he is in dangerous need of a break. If we examine the daydream that Willy had and the way that it meant he had to stop driving as he kept veering off the highway, and the "strange thoughts" that Willy says he is subject to, it is clear that he is a man who is dangerously exhausted and whose job has swallowed him up. This is why, in response to being told about not being able to drive the car, Linda says:
Willy, dear. Talk to them again. There's no reason why you can't work in New York.
Linda clearly feels that for a sixty year old man it is too much for Willy to be doing the kind of travelling, every week, that his job requires of him.
Something else we are told about Willy's job is that he clearly feels he is more successful than his boss gives him credit for. Note what he says to Linda:
If old man Wagner was alive I'd a been in charge of New York now! That man was a prince, he was a masterful man. But that boy of his, that Howard, he don't appreciate. When I went north the first time, the Wagner Company didn't know where New England was!
This clearly introduces the element of fantasy into the play, as Willy believes himself to be incredibly successful, but in reality, as the audience soon discovers, he is a failure at his job.
I am not certain we are to learn anything in particular from Willy's job. He clearly works in the garment industry as denoted by a number of clues including that he visits department stores to sell product, that he carries items in sample cases, that he gives the gift of stockings to the woman in Boston, and that Happy at one point talks about Willy's eye for color, but in reality what he sells is meaningless. Willy is a salesman, and Charlie calls him a dreamer. Willy sells himself, and to the degree that customers respond to him he will be successful. To the degree customers do not respond to him, he will fail. Willy sees himself as a frontiersman, discovering new territory for his company. What we can really learn from Willy's job is that it is difficult and he struggles, like a boxer in the ring or like any other person who struggles to provide for his family. Some critics have argued that the play is an indictment of the whole capitalist system, but that is not the point. Willy is a man alone, and his job gives him meaning and purpose. The company does not respect him and loses its use for him, so it casts him aside. That does no, however, devalue the man. Willy's destruction is not caused by his work but by the rest of his life and its problems. Again, it is Charley who ennobles Willy when he says "Willy was a salesman. No one dast blame this man. A salesman's gotta dream, boy." Ultimately we learn that life is a struggle and each of us is ultimately alone in the harsh world of business. It is the family that truly gives one support and value. If we allow ourselves to think only the job gives us meaning, we will suffer a sad disillusionment at some point.