Why were your earlier ambitions dumb?
Some examples: Collections of any kind. Dominance in any game. Completeness of any endeavor.
I'm finding I enjoy getting as good as I can at some things. But I ultimately don't care how good I am. Easy example is biking. I'm having a ton of fun getting as fast as I can going up a hill going home. Even though Strava is amusingly letting me know that there were over 500 folks that are much faster than I am on the same hill. (To its credit, they put much more emphases on Personal Records than they do on how you are doing against others.)
Same for some series. I ultimately don't care that I haven't read every last book of some series. More, if I really want to know how the latest Marvel movie has turned out, wikipedia is much faster and just as fulfilling for me.
As I've aged, my perspective has become 'many of the things I spent time on'. I can make more money.
As far as how to spend that time, I try to spend a lot on a few exceptionally valuable things. Donald Knuth expresses it well when talking about email: Email is a wonderful thing for people whose role in life is to be on top of things. But not for me; my role is to be on the bottom of things. What I do takes long hours of studying and uninterruptible concentration.[0] (I'm not Knuth so I can't say it's my role, but it's my goal.)
For my personal life, I've decided that nothing is more valuable than loving relationships (platonic or romantic), so that is where I try to spend my time.
I almost posted something about having nothing being worth more than my relationships. I certainly feel that, to a large extent. However, I also have trouble separating my work from my life. To the extent that I'm not even sure I want to.
And I think there's a certain humility to be found in that, in identifying yourself with your work, and a job well done, as opposed to your work being about you, a reflection of your ego. (Those two ideas might sound like they're the same thing, but I don't think they are.)
Identity is often contextual. When you're with friends, you're one person, when you're at work, you're another, and yet a third with relatives. You can hear it when people's accents change when talking on the phone, their bearing changes according to their interlocutors. If who you are is the sum of the contexts your exist in, full retirement is a kind of death.
In large, we are defined by what we define ourselves by. Sure, there are extreme cases where the world defines someone or something. But by and large, those are the exceptions.
I don't think we get to define ourselves. I think we are mostly the sum of our responses to stimuli.
However, it also means you are not necessarily held to any external definition.
I think this view has serious limits. In large, being in complete control of yourself is a luxury most people don't have. To that end, the views that folks can somewhat legitimately hold of themselves are greatly limited by their circumstances.
To play with both of our views together, the interpretations that you can honestly hold are going to be the responses of the stimuli you are subjected to.
Which is my way of saying to try not to get hung up if you are disappointed with any of the current state. It is, in many ways, fleeting. Keep what you can of what you like. Similarly, though, the fleeting nature of things is also irrelevant. If you liked something, continue to have liked that thing. No reason to change, unless you want to.
This sounds slightly contradictory to my earlier point. However, the things I collected now hold no value. That I collected them, though, I can fondly remember. If that makes sense.
I used to argue that, but it omits our entire internal life. Our internal lives are so much greater in scope and, I think, by far the majority of our experiences.
I am ridiculously happy that I didn't get involved at this when I was younger. The "arms race" that is cycling gear is borderline absurd. I finally splurged and bought ultegra wheels, which cost more than my first few full bikes. Probably combined. I am enjoying them, but am very thankful that I'm not optimizing for every last ounce of weight I can.
Were I to start again I would use defined models to refine those ambitions. I would analyze them and refine them again and again, the more important they are. Which is to say, my _current_ ambitions are much more refined, flexible, well-modeled, than they have ever been.
[I work with people and coach them on this stuff, and so here I have to say: I don't recommend this course to everyone; this is me relating my own experience. To some, a process like ongoing analysis has a similar effect to removing one's computer's cooling system, and so they shouldn't worry so much about analyzing things.]
If I set out to do something today, I am much, much more likely to succeed. My life has been transformed (see profile). I temper this by saying that this dumb-talk is as much a warning to my future self as it is a lamentation. But recent measurements of my personal health and happiness do seem to indicate that my recent ambitions are much less dumb. If future-me has any complaints he can talk to the spreadsheet, he can talk to the journal, he can talk to the people to whom I listened more, because I was more mature.
I do think I was an intelligent person overall when I was those ages, and hindsight is 20/20, but yeah, still those were dumb ambitions and my happiness suffered measurably.
I don't see "overcoming dumbness" as a neverending pursuit, either. Evidence seems to show that you can minimize your dumbness until its effect is like rolling a 1 on a d100, then a d1000, and so on. In university I believe I had maybe a d10.
Take a simple technology like saying "I'm sorry. I messed up. Can I get a do-over?" That move right there can potentially level you up to a d100.
I am semi-tongue in cheek here, so I hope I don't burn too many of a reader's analysis cycles. Better to learn this stuff yourself through trial and error.
I remember being shocked when a professor told us undergrads in a very respectful way that we were "dumb undergrads." But you know what? He was right in a big way.
In retrospect, it's just, why? Ok, so you become the best. Now what?