No matter which road is chosen it "will make all the difference" just as every decision we make "makes a difference" to alarge or small degree. The difference can be positive or negative, but all of our choices affect us in some way. Large decisions like where to go to college or what job to take may affect where we live, who we meet and how we live. Small decisions like what we eat may affect how we feel later that day. In the end, all of our choices have consequences.
It wouldn't matter. The roads were both the same.
This poem isn't really about individualism. It is about how we people fool ourselves into thinking that various decisions matter when they really don't. The poet says that both roads really were the same and that it is only later in life, when he looks back, that he will say that one of the roads was less traveled by.
So I would like to think that I would choose randomly because I would like to think that I am insightful enough to know that some decisions don't really matter. I like to think that I would not fool myself into thinking I was making some life-changing decision when I really wasn't.
As did the speaker in The Road Not Taken, I would have taken "the one less traveled by." I am a hard core individualist and am very comfortable taking less traveled roads, marching to a different drummer, and any other cliches you may wish to use.
The speaker in the poem recognizes the potential validity of the more traveled road. The two roads are both undisturbed by travelers at that point and there appears to be no obvious advantage to one over the other:Though as for that the passing there Had worn them really about the same
The decisive factor for the speaker is that one road "wanted wear"; it was not as commonly used and so would provide perhaps more challenge, certainly a different type of adventure than the norm for most travelers. The speaker notes that the more traveled road might be visited "another day" but recognizes that life's paths seldom circle back around to make such a return visit possible.