Successful inventors get to where they are by challenging the status quo. But constantly asking why things are they way they are, they come up with ingenious and clever solutions to problems. Entreprenures are even told to constantly ask why. Why this, why that. And if not, why not!
The problem is, there is a point when you just have to accept that somethings are they way they are for a reason. Persistantly badgering your development team for features and asking why it can’t be fit into the current schedule isn’t going to win you an award for the most forward thinking manager and isn’t exactly going to make you friends with your team. Why can’t you work more hours? Why do you have to go home? Why hasn’t this work been done?
Asking the question why should be a positive thing, don’t make it negative.