WILLY: That’s just what I mean, Bernard can get the best marks in school, y’understand, but when he gets out in the business world, y’understand, you are going to be five times ahead of him. That’s why I thank Almighty God you’re both built like Adonises. Because the man who makes an appearance in the business world, the man who creates personal interest, is the man who gets ahead. Be liked and you will never want. You take me, for instance. I never have to wait in line to see a buyer. "Willy Loman is here!" That’s all they have to know and I go right through. (Act 1)
Willy's exaggerated sense of pride suggests his underlying insecurity and desperate concern over meeting his own inflated expectations. It's highly likely that this unfortunate but annoying personality trait is the very reason why everybody makes fun of him. Ironically, it may just stand in the way of him achieving anything to be proud of.
WILLY: You and Hap and I, and I’ll show you all the towns. America is full of beautiful towns and fine, upstanding people. And they know me, boys, they know me up and down New England. The finest people. And when I bring you fellas up, there’ll be open sesame for all of us, 'cause one thing, boys: I have friends. I can park my car in any street in New England, and the cops protect it like their own. This summer, heh? (Act 1)
Despite evidence that Willy has few friends and is unsuccessful, his inflated sense of pride leads him to insist he is well-liked. Biff and Happy are completely enamored with their father when they are young; they totally buy into Willy's B.S. Later on, however, his failures become all too clear.
WILLY [continuing over Happy’s line]: They laugh at me, heh? Go to Filene’s, go to the Hub, go to Slattery’s. Boston. Call out the name Willy Loman and see what happens! Big shot!
BIFF: All right, Pop.
BIFF: All right! (Act 1)
Willy's pride reflects his increasing blindness to reality. He insists on pretending like he's really successful when it's just not true. In some ways this is really understandable, and it makes Willy seem totally human. It's probably a really hard thing to admit that your entire life has been a total flop.
WILLY [sitting down at the kitchen table]: Huh! Why did she have to wax the floors herself? Every time she waxes the floors she keels over. She knows that! (Act 1)
Willy's disgust at Linda waxing the floors herself suggests his false pride about their economic status. They clearly cannot afford to hire someone to wax their floor, yet he constantly wants to pretend that this isn't so.
CHARLEY: You want a job?
WILLY: I got a job, I told you that. [After a slight pause] What the hell are you offering me a job for?
CHARLEY: Don’t get insulted.
WILLY: Don’t insult me. (Act 1)
Willy has always tried to act like he is cooler than Charley. In reality, though, he's always been really jealous of his neighbor. When Charley offers Willy a job, it hurts Willy's pride. If people know that he's working for Charley, then there will be no denying the fact Charley has done better in life—and Willy's delusional pride just won't allow that.
LINDA: Willy, dear. Talk to them again. There’s no reason why you can’t work in New York.
WILLY: They don’t need me in New York. I’m the New England man. I’m vital in New England. (Act 1)
Willy falsely insists that he is a critical player in his business in order to bolster his sense of self-worth. Even though his sales haven't been good for a while, he argues that he is a really important man.
CHARLEY: I offered you a job. You can make fifty dollars a week. And I won’t send you on the road.
WILLY: I’ve got a job.
CHARLEY: Without pay? What kind of a job is without pay? [He rises] Now look kid, enough is enough. I’m no genius but I know when I’m being insulted.
CHARLEY: Why don’t you want to work for me?
WILLY: What’s the matter with you? I’ve got a job! (Act 2)
Despite the complete absurdity of refusing Charley's job offer (considering his financial circumstances), Willy's pride prevents him from accepting. Willy is determined to pretend like he doesn't need Charley's help even while he's asking for it.
HOWARD: Where are your sons? Why don’t your sons give you a hand?
WILLY: They’re working on a very big deal.
HOWARD: This is no time for false pride, Willy. You go to your sons and tell them that you’re tired. You’ve got two great boys, haven’t you?
WILLY: Oh, no question, no question, but in the mean time… (Act 2)
Howard recognizes Willy's pride as means of hiding from reality. Though Howard does wash his hands of Willy in this scene, in a way he's trying to help the old salesman. If Willy would only recognize the reality of his situation, he'd be able to get by.
WLLY [the last to leave, turning to Charley]: I don’t think that was funny, Charley. This is the greatest day of his life.
CHARLEY: Willy, when are you going to grow up?
WILLY: Yeah, heh? When this game is over, Charley, you’ll be laughing out of the other side of your face. They’ll be calling him another Red Grange. Twenty-five thousand a year. (Act 2)
Willy's exaggerated sense of pride about Biff is an extension of his own fears and insecurities. If Biff turns out to be a failure, then Willy will feel like he's a failure as well. Like many parents, much of Willy's personal pride is based on the success of his children.
WILLY: I—I just can’t work for you, Charley.
CHARLEY: What’re you, jealous of me?
WILLY: I can’t work for you, that’s all, don’t ask me why.
CHARLEY [angered, takes out more bills] You been jealous of me all your life, you damned fool. Here, pay your insurance. [He puts the money in Willy’s hand].
WILLY: I’m keeping strict accounts. (Act 2)
Willy's sense of pride irrationally prevents him from accepting a job working for Charley—but allows him to accept loans he will undoubtedly be unable to repay. Charley is an incredibly generous guy, considering how badly Willy treats him.
BIFF: I stole myself out of every good job since high school!
WILLY: And whose fault is that?
BIFF: And I never got anywhere because you blew me so full of hot air I could never stand taking orders from anybody! That’s whose fault it is!
WILLY: I hear that!
LINDA: Don’t, Biff! (Act 2)
Biff recognizes that false pride is a barrier to success. The failures of his life have made it impossible for him to ignore the fact that he's just not as cool as his father always tried to make him believe he was. Where is the line between instilling your children with a good self-image and making them too big-headed for their own good?