I've spent forty years in the business. Never once have I seen a project of any size get overestimated, not even one time.

I think I mentioned that I told a boss once, the notorious Vinnie Falco, that if these were real estimates, then half the time we'd estimate too high - which is simple logic.

He told me that if I ever estimated too high, I'd be fired. What a charmer!

I am actually pretty good at realistic estimates and if a manager really wants them, I'll give them a good estimate.

But usually it goes like this: "It would take two weeks to write, and another two weeks to productionize." "Oh, we need to get it done in two weeks." "Sure, whatever you like."

Then I end up taking 3 to 5 weeks, and of course the boss is all over you every day after the first two weeks, but it has no long term consequences, because everyone else is behind schedule too.