Metaphorically speaking, someone who takes 'the road less traveled' is acting independently, freeing themselves from the conformity of others (who choose to take 'the road more often traveled'), generally making their own choices, and perhaps leaving a new trail that will become the road more often traveled (until, of course, someone takes the road less traveled from there, and happens upon something even better than the first improvement; in that way, the cycle always repeats itself
