I know how you feel, raking through the past and looking at how you could have done things differently if you only had known better at the time can turn into a favorite pastime.
There's certainly some stuff I did or didn't do that I could cry over to ma heart's content, and tell myself if I'd only been aware of this, if I'd only been a different sort of person, if I'd done things differently, surely it would be different now, maybe it would be better now.
But fact is I don't know, and there's a lot little I doesn't know but doesn't like to admit to. First I don't know whether my soul didn't intend to head down a certain path for reasons my mind simply can't perceive. And then how much of the Universe can my mind really grasp? Very little.
So good chance is that my ordinary mind can just perceive a few paths through life which it considers the best route and a shortcut to happiness, but the soul who's got a better overview sees all ways that lead to where it wants to go and knows better and like a build-in spiritual navigation system in direct contact with the source of creation, it chooses the path to where I want to go all the time, every time I deliberately or by chance fail to follow instructions.
So even in those cases where I can't believe my soul wanted to take a certain byway and that I choose it by mistake courtesy of being human, I can at least believe that my soul can't be tricked but is still on route and will get where it wants to go.
I find that a comforting thought.