Willy goes to see Howard, his boss, to ask him for a settled job in New York instead of having to travel all the time. He finds Howard totally wrapped up in a new tape recorder he has just bought. Howard insists that Willy listen to it too, to the recordings of his family, and even when he finally gets around to hearing what Willy has to say, he doesn’t seem very interested. In fact, far from granting Willy’s request for a New York Job, he fires him. Willy is getting old and has not been making very good sales, and so Howard doesn’t want to keep him on any longer.
Willy is utterly shocked and in despair resorts to trying to impress Howard with stories of his past career and life. He tells Howard about an old and rich salesman he met once, called Dave Singleman, who inspired him to become a salesman himself. Willy paints Singleman’s career in glowing colours. Singleman was the role model for Willy, but he has not been able to emulate Singleman’s success. He goes on to give his own reason why:
In those days there was personality in it Howard. There was respect, and comradeship, and gratitude in it. Today it’s all cut and dried, and there’s no chance for bringing friendship to bear – or personality. You see what I mean? They don’t know me any more. (Act II)
Willy, then, does not put the blame on himself for his failure - he says the times have altered instead, and salesmen are no longer respected and valued, as they were in Singleman’s day. He is also implying strong criticism of Howard here, as Howard is one of these cold, ‘cut and dried’ businessmen who think nothing of oldfriendships and connections. Willy has been with Howard’s firm for over thirty years and was a good friend of Howard’s father Frank, but this means nothing to Howard; he can discard Willy with barely a second thought.
Howard’s dismissal of Willy’s connection with his family is given ironic emphasis when he is shown as being totally preoccupied with his wife and children’s voices on his new tape recorder, while ignoring his father’s great friend who is standing right in front of him.
Dave Singleman was only a casual acquaintance, but he made a big impression on Willy Loman. Singleman appeared to be a big success as a traveling salesman. He appeared to be famous and popular throughout his extensive territory. Most importantly, this man was eighty-four years old and was still on the road. He was so well-known and well-liked that he didn't have to work very hard. The orders would fall into his lap. He had reached a point in his career at which he no longer had to do cold calling or hard selling. He could just pick up the phone in his hotel room and write down people's orders without stirring. It looked to Willy as if a salesman's life could become easier and easier because he would keep making new friends who would all welcome and accommodate him.
Singleman was one of the reasons Willy didn't plan ahead. He thought he could go on selling, if necessary, into his eighties. He didn't think about retiring because he didn't want to retire. A lot of businessmen are like that. They only know one thing, and they would feel lost and useless if they had nothing to do but sit around their house and read the newspaper and talk to their wives. A lot of businessmen die within a few years after they retire. Willy does not have Singleman's constitution. Willy is only sixty-three and the life of a traveling salesman is already beating him down. The stage directions at the opening of the play say that Willy looks "exhausted." Linda tells their sons that Willy is "exhausted." He has a huge territory to cover. The roads in 1949 were not like the divided highways that have been built all over America since then. The cars are much better now in every respect than they were in those days. Willy apparently had to cover his entire territory each time he went on the road. He drove all the way from New York City to Maine and back in a single week. That is 1400 miles of highway driving plus the incidental driving around in towns and the few large cities that existed in New England at that time. New England has very harsh winters. It is mountainous. The inhabitants are notoriously thrifty and hard-dealing Yankees.
His wife persuades Willy to ask Howard to let him work locally. But Howard cares absolutely nothing about Willy's exhaustion or his financial problems or anything else about him. It seems obvious that Willy would have a tremendous task readjusting to working in the biggest city in America at his age. If Howard needed another salesman in New York he would hire a young man. Howard doesn't even understand Willy's situation. He thinks Willy must have a maid and that he could afford to buy an expensive wire recorder when he has a hard time paying to keep his refrigerator running. At age sixty-three Willy has nowhere else to go. Businesses don't hire new employees who are only a couple of years away from the usual age of retirement. From Howard's point of view what Willy is asking is out of the question.
Who is Dave Singleman, anyway? And why is he still working at the age of eighty-four? He may have been lying about all his friends and well-wishers. He may still be working because he has to keep working. The name Singleman seems intended to suggest that he is not married. Unlike Willy, Dave Singleman may never have had a wife or children to support and a mortgage to pay off. He may like the life on the open road just because he is single and has no home to return to. At least he gets to talk to people. He may be earning just enough to pay for his meals, hotel rooms, and gasoline. He may be getting a few orders here and there out of charity. He was an inspiration to Willy but a bad inspiration. And furthermore, the name Singleman also suggests that he is a single, unique example of a man who can continue to lead the gypsy life of a traveling salesman at such an advanced age. Chances are that Singleman is selling lighter-weight merchandise than Willy and doesn't have to carry two heavy sample cases around with him. Willy shouldn't have based his entire life on a single example of a single salesman who was a virtual stranger. Willy is gullible. He takes the word of one man that the life of a traveling salesman is luxurious and glamorous. He takes the word of his old boss, Howard's father, that he will always be appreciated and favored by the company. Willy believes in illusions. An illusion is something a person believes because he wants to believe. Without his illusions, where would Willy be? His is not the American Dream but the American Illusion.