Who is the speaker in "The Road Not Taken"? What is he remembering?

The identity of the speaker and the nature of the choice in “The Road Not Taken” are deliberately left uncertain so that any reader can identify with the situation.

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The first-person speaker in "The Road Not Taken" could be anyone. There is no indication of the speaker's sex, race, age, or nationality. No detail is given, except that he or she shares with the rest of humanity the inability to be in two places at once. This adds to the universality of the poem. Everyone has been in the position of having to make a choice without being able to guess what the consequences will be. The lack of specificity allows readers to put themselves in the position of the speaker.

The situation the speaker is remembering is made universal in a slightly different way. Though there are no details given about the speaker, there are plenty of details about the wood and the path. These images make the poem more vivid, but they do not have any effect on the general applicability of the metaphor. It is common to speak of paths and roads through life in any case. The opening of the Divine Comedy is perhaps the best known of many instances in literature. The speaker is recalling a choice he (or she) had to make, but, beyond this simple fact, the nature of the choice is left as open as the speaker's identity.

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In Robert Frost's poem "The Road Not Taken," the speaker is not identified by gender or age because the speaker could be anyone. 

Essentially, the poem is about how it is human nature to want our lives to have meaning and purpose. Humans do not simply recount a series of memories, but they combine those memories to tell a story and to teach or inspire others.

The speaker in the poem describes himself/herself as a "traveler" who comes upon a fork in the road or "two road diverged in a yellow wood." The speaker uses imagery to describe the paths in stanza two:

Then took the other, as just as fair,
And having perhaps the better claim, 
Because it was grassy and wanted wear;
Though as for that the passing there
Had worn them really about the same,

Upon inspection of the two paths, the speaker concludes that the paths are almost identical: worn "really about the same" and "equally lay." The speaker then choses a path and remarks how he/she will keep the second "for another day," but "doubted if I should ever come back." This is another example of the theme of human nature in the poem. It is human nature to make plans with the  best intentions, but we do not adhere to those plans. 

In the final stanza, the speaker reveals that humans tend to rewrite their memories to make the story of their lives sensical. The speaker acknowledges that in the future he/she "will be telling this [story] with a sigh"

Two roads diverged in a wood, and I— 
I took the one less traveled by, 
And that has made all the difference.
 
The speaker admits that when he/she looks back at this time that the memory will be skewed and rationalized to be a catalyst for change in the speaker's life. But in truth, this was simply another memory; another moment. Frost did not write this poem to cast human beings in a negative light, but he wrote the poem to emphasize how similar we all are. We do not want our good to be interred with our bones (as it was with Caesar). There is a universal desire for our humanity to be remembered. 
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