The best coaching/therapy is the one that teaches you to do these explorations by yourself. Problem is that it's bad for business to teach people to manage issues themselves vs subscribing them to therapy.
It kind of sucks that I'm stuck in the looking for the best solution instead of coming for a solution. I don't do this when I code and I probably should, and for my personal life I do it too much and probably shouldn't.
I would assume you trust your gut wrt to code: when you come up with a good enough answer you know what the tradeoffs are or at least have confidence that you can fix whatever comes up.
Wrt personal life/feelings, it has helped me talk to therapists and friends who've had similar issues and hear what they did to develop my own intuition.
It's tough! The computer throws errors but feelings are less deterministic and reflective (they change our ability to look into them).
