And almost everyone gets it wrong. This is the most remarkable thing about “The Road Not Taken”—not its immense popularity (which is remarkable enough), but the fact that it is popular for what seem to be the wrong reasons. ...
Most readers consider “The Road Not Taken” to be a paean to triumphant self-assertion (“I took the one less traveled by”), but the literal meaning of the poem’s own lines seems completely at odds with this interpretation. The poem’s speaker tells us he “shall be telling,” at some point in the future, of how he took the road less traveled by, yet he has already admitted that the two paths “equally lay / In leaves” and “the passing there / Had worn them really about the same.” So the road he will later call less traveled is actually the road equally traveled. The two roads are interchangeable.
According to this reading, then, the speaker will be claiming “ages and ages hence” that his decision made “all the difference” only because this is the kind of claim we make when we want to comfort or blame ourselves by assuming that our current position is the product of our own choices (as opposed to what was chosen for us or allotted to us by chance). The poem isn’t a salute to can-do individualism; it’s a commentary on the self-deception we practice when constructing the story of our own lives. “The Road Not Taken” may be, as the critic Frank Lentricchia memorably put it, “the best example in all of American poetry of a wolf in sheep’s clothing.” But we could go further: It may be the best example in all of American culture of a wolf in sheep’s clothing. ...
It’s an explanation that Frost himself sometimes encouraged, much as he used to boast about the trickiness of “The Road Not Taken” in private correspondence. (“I’ll bet not half a dozen people can tell who was hit and where he was hit by my Road Not Taken,” he wrote to his friend Louis Untermeyer.)
--David Orr, The Paris Review, on the important of reading the whole context. HT: TS
And sorry I could not travel both
And be one traveler, long I stood
And looked down one as far as I could
To where it bent in the undergrowth;
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,
And both that morning equally lay
In leaves no step had trodden black.
Oh, I kept the first for another day!
Yet knowing how way leads on to way,
I doubted if I should ever come back.
I shall be telling this with a sigh
Somewhere ages and ages hence:
Two roads diverged in a wood, and I—
I took the one less traveled by,
And that has made all the difference.