This classic American poem is iconic, but almost universally misunderstood. Many read it to mean that taking the road less travelled makes all the difference, a commentary on the benefits of individualism. While there are definitely good arguments to be made for individualism, this is not what Frost wrote about.
It’s interesting to note that Frost wrote the poem as a personal commentary on his friend, Edward Thomas, who took regular nature walks with Frost. Thomas was indecisive about leaving to join the war effort, and would regularly lament taking one path over another during his walks with Frost. His constant indecision and reflective laments amused Frost.
In the poem, it’s tempting to focus on the final lines: “Two roads diverged in a wood, and I— / I took the one less traveled by, / And that has made all the difference.” But those lines are preceded by these two lines, which put it in context, “I shall be telling this with a sigh / Somewhere ages and ages hence:” … As you can see, there is no actual declaration here—the speaker is imagining how, from the future’s perspective, meanings in the hindsight of life’s choices are manufactured (where they don’t exist). Like Edward’s constant (and amusing) reflection, these lines explain that in the future, the speaker will imagine the road he took made all the difference.
How do we know this is what Frost meant? Well, setting aside Frost’s own commentary, let’s look at how Frost describes the actual roads. He writes:
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.
It’s obvious that both paths are equally trodden, neither being a road “less travelled by” but “equal.” The only difference between how well traveled these two roads are is found in the imaginings of the speaker, how his future self will reflect on the choice (which is no real choice at all) between the two paths he could have taken.