Well, after choosing his path, the Frost says he looks forward to a day far in the future when, “with a sigh,” he will tell people about taking the road “less traveled by, and that has made all the difference.” Does this mean that taking the one less traveled has “made all the difference” in a good way? Saying so “with a sigh” doesn’t necessarily sound like a good thing. The poem isn’t at all clear on whether or not taking the less traveled path was a good choice or a bad choice. So, while the poem is clear that all of our choices shape the path we take in life, it’s more ambiguous about whether choosing “less traveled” paths is a good thing or not. You won't know if you made the right choice until you are well into retirement.