“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.” From the article The Most Misread Poem in America by David Orr in the Paris Review.