The Irony of Authority
Dressler is introduced as the owner of a cigar shop. He possesses some capital of his own, which is no joke for his socio-economic position. The irony here is that he chooses to leave behind this ownership in order to work for somebody, in an entry level position at the Venderlyn Hotel. Dressler willingly accepts a lower position because he's convinced that this title holds more potential than his small shop. He chooses exterior growth to interior, which is ironic because Dressler frames this endeavor as an opportunity for personal progress, something elusive under the overbearing expectations of middle management.
The Irony of Management
When Dressler is promoted, he immediately loses satisfaction with his job. While previously he was intent upon climbing the proverbial ladder, he quickly realizes that's not the path he desires. He wishes to be the leader of a network, something which his position at the hotel makes nearly impossible, despite his original intentions when coming to work at the hotel.
The Irony of Achievement
Millhauser's book is designed to outline the "success" of the American Dream, but this is in itself an illusion. Dressler learns, by continually chasing success, that it's a myth. He cannot find satisfaction through exterior sources. This illusive dream that everyone talks about is merely a manifestation of incentive, designed to promise future rewards which only fade once a person has invested too much to turn around.
The Irony of Independence
Dressler finally decides that he wants to be his own boss more than he cares about making a great deal of money. He decides to compete in the hotel business, borrowing from his sister-in-law. As an independent business owner, he believes he will achieve the satisfaction of accomplishment which he lacked at his management position at the hotel and the incentive which his restaurants lacked. Ironically, this new-found independence only ensures Dressler's dissatisfaction because now he is solely responsible for achieving success and awarding himself satisfaction, which he does not.
The Irony of Contentment
Throughout the novel, Dressler is looking elsewhere for happiness, meaning, and satisfaction. He believes that whatever he is not currently doing must hold the key to these elusive states. Unfortunately for him, he has the problem backwards in his head. The key to unlocking satisfaction and living a meaningful life must begin internally, with an active contentment for the present. Because Dressler is constantly looking outside of himself or beyond his capabilities, he forgets to notice and enjoy the beautiful experiences around him, which could fulfill his desires internally without any external change.
