If (for any reason) we know that dreams cannot be achieved, there is a clear cut. And while it might take time to accept the situation, this realization is Stoic/Zen.
It is way harder if there is a chance, we try, yet fail. When do we keep trying, and how do we do so without losing hope piece by piece? It might be even harder when the dream is not something like "win a gold medal in snowboarding", "build a unicorn startup" or "publish a bestseller". But it is in the line of having kids, or being healthy, or other things that a lot of people take for granted.
Besides that, we can't achieve everything, we could not be everywhere when something interesting happens there, at the very least because a lot of those things happened in the past, or do everything because physical condition, economics, or extra conditions (i.e. being an astronaut).
So you draw lines. This is what I can do, I can go, I can be. You may push boundaries, but in the end it will always be more things outside than inside. And try to be the best on what matters on those boundaries.
Things have changed, but it takes some of the financial anxiety away when I remember that I would still give up everything to go back to that time.
Sitting and thinking for 10 minutes about snowboarding when your knees are blown out is 10 minutes you could have used differently.
Everyone has regrets but my attitude is: I can’t change the past, but I can change the future.
10 minutes doesnt sound like much of a loss, even if you do it every day. Maybe it helps you empathize with athletes, or if you get nostalgic/wistful, it helps you explore the range of emotions, which is fine as long as you don't get stuck with them.
Future me can suck it. I'll be selfish in the moment.
This is like watching videos of old folks saying: "I wish I took better care of my teeth". Right, cause thats what matters a lot to you now.
The lesson to be learned is that what you want from life changes. You shouldn't prioritize the needs of a future version of you.
I'd argue that snowboarding wasn't author's "dream" to begin with. I think it's reductive and unfair to compare your "oh it would be cool to do that" with someone else's actual dream: as in, a passion they pour their life and soul into. Being great at anything takes much more than a passing "it would be neat to be able to do X."
And achieving a dream (say, competing at the Olympics) is a lot less glamorous than a casual tourist might imagine.
Indeed the underlying insight that our lives are arbitrarily small and irrelevant, (yes, even the greatest titans of politics, tech, science and art), that drives the tech-elite long-now accelerationist ideal. Every life is characterized by [trade-offs + luck] and none of them have any meaning unless we get through the Great Filter. (Sure, this belief is mostly a post hoc rationalization to just do what you wanted in the first place, but I appreciate the attempt to paper over the naked self-interest.)
I think this sort of underplays the feeling of "lives unlived, paths not taken" that everyone gets hit with. Just flattens the whole thing that had been building up to that point, instead of allowing it to open up further.