Robert Frost is a deceptively simple poet. In this poem, the speaker, out for a walk, comes to a fork in the road. Which way should he take? It's a poem about decision, life choice. Choosing one's "way" in life. On the surface it's a minor event in a life, but taken metaphorically (which the speaker urges us to do), the event assumes symbolic proportions. Why has his choice of the road less travelled "made all the difference"? Has it made all the difference?
We can deconstruct a latent cultural assumption, one I'll call the Sinatra function ("I did it my way"), loaded with the ideology of American rugged individualism, of the self-made man, of the man who dares to be different, to strike out for gold. The poem's speaker projects forward to some distant day, when looking back on his uncharted, bumpy path of progress, he can say with a sigh of satisfaction, 'ah yes, it was all worth it in the end.' Taking the less travelled road made all the difference in my life. One can almost cue the Apple logo and the grammatically faulty tag line: "Think Different."
But Robert Frost was no sunshine superman. His is not a poetry of boundless optimism. His life and his work is peppered with depression and doubts. To ignore this tenor in his work when reading the poem is ill-advised. The poem is fraught with ambiguity. What kind of "sigh" is that in the last stanza? One of relief, of regret, or a little of both? Or is Robert Frost undercutting the whole idea of making such projections? How is one to know where the road of life leads? How long and how hard? In fact, we can push back against the poem's closing rhetorical flourish: will it have made a difference? Will it really? Is life that contingent? Are life choices always a zero sum game? What if none of it matters? What if this is a poem about the way in which people fabricate meaning and assign significance to even the most mundane of choices? Perhaps these are necessary illusions, the costumes we dress our lives in to make them relevant and meaningful. Remember, each road is more or less the same. Maybe it is how we think of them in retrospect that makes all the difference.
I see at least three interpretive options here: (1) the Sinatra function, also known as the Sigh of Satisfaction, (2) the Sigh of Regret (why on earth did I choose the wrong road), and (3) the vertigo function: an existential onslaught of decision and indecision, which must be repressed in order to assume either position (1) or (2). Maybe this decision is critical to my fate; maybe it's commonplace and meaningless, but I will invest it with meaning anyway.
Quote from William H. Pritchard “On the Road Not Taken”
“Yet Frost had written Untermeyer two years previously that "I'll bet not half a dozen people can tell you who was hit and where he was hit in my Road Not Taken," and he characterized himself in that poem particularly as "fooling my way along." He also said that it was really about his friend Edward Thomas, who when they walked together always castigated himself for not having taken another path than the one they took. When Frost sent "The Road Not Taken" to Thomas he was disappointed that Thomas failed to understand it as a poem about himself, but Thomas in return insisted to Frost that "I doubt if you can get anybody to see the fun of the thing without showing them and advising them which kind of laugh they are to turn on." And though this sort of advice went exactly contrary to Frost's notion of how poetry should work, he did on occasion warn his audiences and other readers that it was a tricky poem. Yet it became a popular poem for very different reasons than what Thomas referred to as "the fun of the thing." It was taken to be an inspiring poem rather, a courageous credo stated by the farmer-poet of New Hampshire. In fact, it is an especially notable instance in Frost's work of a poem which sounds noble and is really mischievous. One of his notebooks contains the following four-line thought:
Nothing ever so sincere
That unless it's out of sheer
Mischief and a little queer
It wont prove a bore to hear.
The mischievous aspect of "The Road Not Taken" is what makes it something un-boring, for there is little in its language or form which signals an interesting poem. But that mischief also makes it something other than a "sincere" poem, in the way so many readers have taken Frost to be sincere. Its fun is outside the formulae it seems almost but not quite to formulate.”