Estimates are for projects where you know what you're doing. You can estimate home construction because you've built a home before. I can estimate the happy path. I can't estimate edge and corner cases until I get closer to the edge or corner. It's not even there until I get close to it. I strongly agree with these statements from the article: >"Tasks with the most uncertainty (rather the biggest size) can often domi…
You're not asked to be prescient -- just estimate an interval that is actually statistically useful.
The 5 % worst case events that blow up and take months when you said days, those need to be handled separately, differently.