Why Is Estimating Difficult?

Estimating is difficult because by definition, you're doing something you haven't done before. You don't know exactly what the thing is that you are trying to estimate - especially in software. Even if we somehow gained skills at it, most of the time, the definition is such that we can't,. It's not defined. We can't estimate something that isn't well-defined. And so, a very, a very poor behavior or response to that is to say, look, this is tough. So, let's just throw up our hands and not give an estimate. When it's done, and we'll figure it out along the way," he says.