I've got a question for you here, what is a wise use of estimation?
What problems are estimates the ideal solution for? In the context of software development?
I can think of only two: planning headcount and priorities (aka planning the order in which you do things).
When you focus on those problems, you realize there's no need for an accurate estimate. All you need is relative sizing between requests. This seems twice as much work as that but gives us half the benefit. Ok probably we shouldn't do this one first. And even then, often time impact is all you need for priorities. Like who cares what takes you longer, if you just focus on building the next most impactful thing you'll very often succeed.
The question of: "When are we going to be done this?" Is almost always irrelevant except for what I mentioned "asking for a quote". Like, who cares when it's done? What else you'd rather we do? I can tell you if your alternative will be any faster or not. And is this not the most impactful thing? If so, let's finish it and stop slowing us down with these irrelevant questions.
Now for headcount, it's the same thing. Look how much you did last year with what headcount. Ask yourself if what you're hoping to do this year is of the same relative size, twice as big, half as big, or smaller? And then plan headcount accordingly. If twice as big, double head count. Overtime you'll learn if twice as big requires doubling headcount or 1.5x or 1.2x or 2.3x etc.
