One I encounter at work fairly frequently is “Don’t let perfect be the enemy of the good” and “If you don’t have time to do it twice, do it right the first time”.

The reality is that you need to develop a sense for when you’re just spinning your wheels trying to anticipate anything and everything possible, and pit that against the desire to just call something done because it looks like it works in a carefully controlled test situation and you want to move on.

Some things you’re only going to catch after letting your idea/plan/program come into contact with reality, but some things are also far better to plan for in advance.

So you just keep adjusting your “ceiling” and “floor” for how far you go when designing shit, and eventually you build a sense for it.