Professionally I'm a data architect. Modeling data in a way that is functional, performant and forward facing is not an easy problem so it's perfectly fine to struggle with it. We do our best job with what we've got within reasonable constraints - we can't do anything more than that.

I found that over time my senses have been honed to more quickly identify things that are important to deeply study and plan right now and areas where I can skimp more and fix it later if problems develop. I don't know if there was a short cut to honing those senses that didn't involve a lot of pain as I needed to pick apart and rework oversights.