Dumb, yes, dumb. The ambitions were unrefined, unintelligent, and I had no idea how to make an ambition more refined and add more intelligence to it. But the truth is, that is a thing you can and must do.
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.