I don't spend any time thinking about regrets and what ifs and coulda, shoulda, wouldas. I can see now, though, that there were two roads diverging and I took one and not the other. At the times, it wasn't as clear that there were two possible roads. Except once.
I don't know if you were intentionally referencing it but the poem by Robert Frost "The Road Not Taken" as you were hinting at is one of my all time favorites. " Two roads diverged in a wood, and I— I took the one less traveled by, And that has made all the difference". I like to think about that line time and time again to push my self to be eccentric in life and not to be put into ordinary sedentary lifestyle in which I feel society is placing on kids today. Furthermore, I agree about not spending allotted time thinking about it regrets. I tend not too but sometimes it seeps through the cracks at weird times and makes me ponder