I think a non-trivial part of why deadlines are always wrong is something akin to the Coastline Paradox [1], where the closer you are to something, the more det

I think a non-trivial part of why deadlines are always wrong is something akin to the Coastline Paradox [1], where the closer you are to something, the more details there are. At some point you have to just say, "Fuck it. It's good enough" and leave it as the terrible flawed pile of crap it looks like at the detail level you're at. Often once you step back and look at it from a customer perspective, you had just gone in too deep and they didn't need half of what you were preparing for anyway. [1] https://en.wikipedia.org/wiki/Coastline_paradox https://en.wikipedia.org/wiki/Coastline_paradox