I learned that some philosophy dude theorized that as people get older they always regret what they didn't do. But because you can't actually do everything in life, pretty much everyone is forced to reflect on "what if" scenarios.
Maybe regret isn't fully accurate to describe it though, the idea perhaps was more that it is natural to ponder what would have happened if you made a different choice, even about seemingly mundane events. I can't remember the name of the guy who said this though, but I'm sure there is some philosophy sperg here who understands what I'm getting at.
Basically he said like...if you got married or not, you will regret it. If you went to college or not, you'll regret it. The idea being that that because it is not possible to make every choice, it becomes impossible to know if your life would have been better or worse if you chose differently, even if you were convinced it was the right choice at the time.
The more you stack up these situations as you get older, the more you're forced to reflect on them. So I think what truly makes me notice aging (and look im not that old yet but time waits for nobody) is having more "what if" scenarios build up in my mind.
It isn't so much about the grass being greener, although it could be depending on your life, moreso that we are tempted to theorize about the unknown. The older I get the more I feel like I notice other people being unhappy in their lives, it isn't uncommon to see successful people who earned their way up and still be really unfulfilled and confused about their life, perhaps hinting that despite gaining a good amount of money and promotions and shit, none of that had been truly the right choice for them to be actually HAPPY.
So I guess my answer is what really makes me feel "old" is living with all the decisions I've ever made and wondering more about the what ifs. We all have a bunch of what ifs in our past, they pile up and leave us with no actual ability to know if we would be more happy or not. And sadly there is no time machine in real life.
I suppose that is why I feel it is important to go for new experiences...you really can miss your entire life if all you do is hardgrind towards a single, simplistic goal like "get rich" or "own house". Life is all around us every day to explore and experience.
So I guess in the end people are correct when they say life is about the journey and not the destination. We don't kill time, time kills us.