The dilemma of this poem is for us! The dilemma is deciding what Robert Frost meant in his poem 'A Road Not Taken.'As so many people respond so differently to this (including some of the many 'learned critics' who have been cited here and in other questions and answers) we might as well all say how we individually respond to the poem, as has been done by various posters. We can remember that poetry is subjective - we all arrive at a poem from different directions, we 'have traveled different roads', carry different emotional baggage and have had infinite variety of life experiences.
I tend to veer away from the (perfectly valid) idea that Frost is saying it doesn't matter which road you take. For me that it 'made all the difference' doesn't fit here. I perceive the poet saying that we need to look to the future and the past when we choose what paths in life to take. The future - we need to look into the road well to discern where it might take us. The past - how will we look back (and others) on the decision we took?
Frost is sad that he cannot 'have it all' like all of us. A choice has to be made. Luckily for him he made the right one. (Poetry?) Perhaps it is irrelevant that it was the less traveled one. The point was it made him happy so it is being happy with the choice we make that is important. It is the satisfaction that is relevant not the road.
We also might want to remember that the title of the poem is 'The Road NOT Taken' so does it matter so much about the one he took? He's talking about the one he Didn't take.
Here is a link describing Frost's career towards the end of his life,looking back.
A similar question was asked not too long ago (see the link below).
In my response to that question, I challenged the popular reading of the poem. I wrote:
I see the Frost poem "The Road Not Taken" in a very different way than the two previous posters. My reading is supported by at least two reputable sources, which are identified at the end of this posting. Both sources state that the poem can be read one way on the surface (readers often don’t move past this superficial reading, unfortunately) and a very different, more compelling and more complex way if the reader pays close attention to the language of the poem.
In 1961, Frost commented that “The Road Not Taken” is “a tricky poem, very tricky.” The trickiness may lie in the speaker's contradictions in characterizing the diverging roads. At first, the two roads seem very different, but upon closer analysis, these differences all but vanish. The second stanza opens by asserting that the one road is “just as fair” as the other and ends with the statement that “the passing there / Had worn them really about the same.” Stanza three includes a similarly contradictory statement. The two roads do not appear to be different at all; they “equally lay / In leaves no step had trodden black.”
What are we to make of these contradictions? A number of critics argue that the poem actually mocks (with good humor) our tendency to look back on our past (just like the speaker, who jumps forward in time in the final stanza of the poem) and to assign all sorts of significance to our past actions. In reality, we know that there are multiple ways to get to any one place; it often really doesn’t matter all that much which particular road we take.
The whole point of the poem is the dilemma of the speaker and how he agonizes over how to resolve it.
He comes to a crossroads in a wood and doesn't know which way to go. He tries to figure out which way to go, but each time he sort of decides on going one way, he thinks about how the other way seems just as good.
So the poem sees him sort of outthink himself -- thinking first one thing and then the other. By the end of the poem he tells himself that he'll say (one day) that he really took the less-traveled road and that this decision was important.
In this poem the dilema is when the character does not know which road to take. he sees that one of the roads is worn out and it was the mostly prefered. for me these roads are like our lives. because there comes a time in life when we stop and question what our future choice will be. but in the end this character was satisfied with his choice and gave a sigh of relief.