When do i stop sharpening?

In the trade that I am in, there is a category of software called dev tools. These are the tools we use to build software itself, and they are endlessly customizable and extensible.

Lately, I've been struggling to find the right balance. I do believe in sharpening my axe before I start cutting, but I also don't want to be stranded in the middle of the forest while everyone else has already cut down the trees and headed home.