“Sometimes the road less traveled is less traveled for a reason”~Jerry Seinfield
Metaphorically speaking, someone who takes 'the road less traveled' is acting independently, freeing themselves from the comformity 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.
~The road more often traveled
Despite the obvious advantages of taking the road less traveled, there are certain times when taking this path is not always the best choice, and it might be better just to stick with the road more often traveled. Taking another road just to circumvent the road more often traveled, the road that policy is built on, is not constructive. Making the choice of which road to take can sometimes be hard, and is very dependent on the situation.
One must assess the possible advantages, disadvantages and risks of taking either road, just as any real-life explorer or traveler would.