Yup, but it goes both ways. I end up over-eningeering as some feeble attempt to avoid technical debt, only to realise my over-eningeering /is/ the technical debt. Or I end up with relatively simplistic / specialised code that needs an entire rewrite and migration process any time something is added. Either way, it's a bunch of rewritten code mixed with paralysing anxiety about writing bad code.
Get used to, and even good at rewriting. I enjoy it, and I realize that I may never have the best idea of what's appropriate at one point in time, but rather accumulate an approximation over time as I reshape the code to the best of my knowledge. And I develop tools and practices to aid me in refactoring faster and with more confidence. Most importantly, keep throwing yourself into it.
I think we as developers underestimate the value of a 100 line Python script. Everything could be hard coded and inflexible, but it's still easy to refactor because you can keep the whole thing in your head.
