While I was reading your comment I was reminded of a professor I had in law school (for some reason...), he was almost 70, but he still had a ridiculous amount of energy. He had grown a law firm that I believe he sold when he was in his 40s? And then he used some of the proceeds to buy some sort of mechanical equipment company which he grew and then sold like a decade later. He taught a bunch of different business law subjects and he got so excited about some of the driest technical stuff.
I really admired him but I couldn't figure out exactly why, other than that he was successful (but at a fairly highly ranked law school, you're completely surrounded by successful people all the time). One day, I realized that it was because he was, even at his age, still SUPER interested in his own life. That was what I was most impressed with. He had kids and whole bunch of grandkids that he obviously loved and he still had a few business concerns on the side in addition to teaching a handful of courses at the law school. A lot of people that age, even very successful ones, are just kind of running out the clock, for lack of a better phrase, just puttering around and playing golf and wishing they were still doing something worthwhile, watching the news obsessively. But this guy just did stuff he thought was interesting and he did it really well.
Anyway, I'm not sure it's as important to be constantly eclipsing your past achievements as it is to be really interested in what you're doing now. I'm sure when my professor plotted out his life, he wouldn't have imagined all the random stuff he'd do, but in retrospect it's a life filled with accomplishment and apparent purpose.