The poem is an illustration of a common human affliction--grief and regret caused by the loss of another human. Through the use of value progression and the interweaving of denotative and connotative meaning, the speaker shows that no matter how much a person tries to prepare for the loss of one he or she loves, grief and regret are inevitable.
By comparing the phrase "the art of losing isn't hard to master" with the frequently used word "disaster," the meaning begins to take shape. This phrase is used four times in this nineteen-line poem (lines 1, 6, 12, 18). Considered closely with the word "disaster," also used four times, one sees the speaker is making a point of rhyming the words master and disaster to emphasize the denotative point that many losses are not disasters--they can be accepted without grief or regret (3, 9, 15, 19). Yet the phrase "the art of losing..." throws a connotative meaning into the mix by indicating that losing, an uncontrollable event, can be a learned skill. Taken together, the phrase coupled with the word "disaster" provides foreshadowing to the paradox of trying to prepare to lose a person.
The Oxford English Dictionary can shed light onto this interweaving of denotative and connotative meaning.
Art
1. Skill in doing anything as the result of knowledge and practice.
Human skill as an agent, human workmanship. Opposed to nature.
2. An industrial pursuit or employment of a skilled nature; a craft...
Losing
1. The action of LOSE. Perdition, destruction; the being lost or ... to be in process of being lost.
2. The fact of losing (something specified or contextually implied). The being deprived of, or the failure to ...
Denotatively the phrase "the art of losing" means that a person has