I noticed a similar tendency in myself a while back - whenever I saw somebody who was both succesful and young, I'd do a mental calculus in my head to see if I could "catch up", and I'd get bummed if I couldn't (similar to you comparing yourself to a you that had more advantages).

I adopted a similar mindset of "wow, if they can do it that fast, look how much time I have to become successful" - essentially seeing that yes, I could get much further faster if I used their techniques.