Robert Frost’s rather straight-forward “The Road Not Taken” is notable for many things, including its tendency to be misread. A poem often read as an assertive statement on the virtues of individualism is actually a statement on the uni-directionality of time.
There is no going back. As a traveler through life you have only one chance to decide how that life will be lived.
This is the poem’s message. And, as a theme, it actually has very little to do with individualism or non-conformity.
Adding his contribution to the many, many scholarly and critical voices on the matter, David Orr puts in his oar, as it were, at the Paris Review:
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.
Review the poem with this equivalency in mind and you will see that the narrator is expressing regret, not self-congratulation. He wishes he could have been able to take both paths, but as one traveler he cannot take more than one path.
This is a poem that certainly seems to consider, for a moment, ideas of originality and individuality and doing what others have not yet done, but in the end the poem clearly suggests that the true crux of the traveler’s dilemma is not that one can or should choose to go one’s own way but, instead, that one can go only one way.
Frost reportedly wrote this poem as a bit of a joke. A naturalist friend of his that was fond of leading hikes through the woods and pointing out interesting tid-bits along the way often ended the hikes with regret, wishing that he had taken his guest along another path because it would have provided other opportunities for instructive observations.
Alas, each hike had to take but a single path. Regretting that we have but one life to live is, perhaps, worthy of Frost's lampoon if we think for a moment about how this naturalist friend was always sorry that he could not celebrate more varieties, expressions and iterations of flora and fauna. Instead of being glad to have offered a tour of nature, he was troubled by the idea that there was life still left un-remarked and un-celebrated. This is irony and it is a valuable expression thereof.