When is “measure twice, cut once” bad advice?

One of my hobbies is complaining about the tendency of software developers to view choices as binary, moralistic decisions. Measuring twice is obviously correct, and anyone who doesn’t do it is an unprofessional, evil wood waster. Either that or double measurers are a bunch of know-nothing shysters selling snake oil for exorbitant consulting fees. This black-and-white thinking is a mental shortcut that many animals take, but sometimes it’s nice to apply a little more intellectual rigour than a Pomeranian.

I’d like us to think less in terms of right and wrong when it comes to technical decisions, and think more in terms of context, costs and benefits.