You know what? It's POINTLESS.
Yeah, I'm not where I could have been had I figured out all of this stuff earlier - but where I am isn't all bad either. There's always the artistic experience angle, too - I have a greater appreciation for human misery, or something. I've got a lot of life left yet, and I'm not that far off from where I'd like to be. All things considered, I've done pretty damn well for myself.
It won't matter in ten years that I didn't come close to getting university honors. It won't matter in ten years that my wedding wasn't exactly the way I wanted it to be, or that we didn't refinance our mortgage in time to get us that extra thousand bucks. It won't matter in ten years that I didn't get anything done in my first year and a half in the workplace. It will matter that I know I tried my best, and did well considering my limitations at the time.
But it's still so tempting to wonder what might have been. And such a slippery slope from wondering to wishing.