Outstanding writing, and thought.
No answers follow, as usual. Just opinions.
I think there are pretty much only two types of people in the world, in regards to your lament; those that recognize and acknowledge those feelings, and those that are oblivious.
Is it really better to be oblivious? I don't think so, but apparently it is a choice.
But we all just imperfectly strive. The romantic figures in Rand's novels were exactly that; romantic figures. Ideals. Risk is finite, even in imperfectly reaching for personal goals such as those.
Part of the gift of our youth is more a condition of not knowing better. It is not true, in any absolute sense, that when we are young, we are safely surfing far from the rocks; we only think so, because we've witnessed so few wipeouts. The reality is, we are from the moment we are born surfing just inches from potential wipe out in this universe. The rocks are always within reach. It is only time itself that reveals that truth to us, and by the time we understand that, we can either be saddened by that realization or amazed and grateful that we've made it this far to the beach.
Perhaps as we get older, what happens is that more of our wet bits becomes devoted to trying to see the rocks, and in so doing, distracts us from more positive application. We each only get a finite mote of heat and light and animation and wet bit bandwidth to apply; none of that is infinite in any of us. But that is fairness in this Universe. Each and every human who has ever lived has existed under that universal constraint. It is our fair slice of existence.
No, it is way beyond fair. It is a near damn miracle. All of it, even the bumpy parts.
Humor and joy are somewhat related; someday one or more of us, as a consequence of imperfectly striving, will figure out the means and whys and wherefores of our emotional well being. In the meantime, we rely on the wisdom of Marx. Not the asshole Marx, but Groucho Marx, when he observed something like "I'm going to live forever or die valiantly in the attempt." A certain dose of lout is useful in dealing with the miracle/absurdity of the human condition; that is why, from time to time in my life, I've had to rely on the following two words when dealing with failure and adversity: "Fuck it." As in, I'm still here, I'm still swinging. I think my Mom taught me that, though not in those exact words. In her simpler words, passed on from her country girl mother, "You go as long as you can."
The end of many things brings on a certain funk; the Olympics is an example. (Google "End of Olympics Blues") Fortunately, the end of the wash cycle in a washing machine, not so much. As we get older, we can wish to relive our youth, or at least, to have the same capacities for joy and life we remember having as youth. But in fairness, we had our youth, and as a pure bonus not realized by all, we have every following stage of our lives. I don't resent the young at all; I've been where they are. I hope they someday get to where I am, but in that hope, I also know that is not guaranteed. They don't know that, and when I was their age, I am glad I didn't know that, too. That is generational fairness.
I totally enjoyed your piece, and identified with it. I hope you find your way to say "fuck it" and scream "yahoooooo" all the way to the beach, because as ridiculous as that sounds, that is what makes us human, too.