Earlier quoted context omitted.
Estimating is my Achilles heel. Always has been. I'm way too optimistic. My workaround was to do jelly bean estimating. Get guesses from everyone, then use the average. Worked surprisingly well. We did other things to meet that target date, honor that estimate, of course. But that's a longer story.
> Estimating is my Achilles heel. Always has been. I'm way too optimistic. That's kinda the whole point. Everyone sucks at estimating. Scrum proposes a way to do "what greybeards call project management" in a way that deals with this universal inability.
I didn't explain "the other stuff" for why jelly bean estimating works.
The number doesn't matter. It's the shared hallucination (consensus) for the deadline. It short circuited, resolved the debate about "how long". It secures the team buy-in.
Once we had a deadline, we managed the work to match. Closest analog I can think of is Kickstarter: initial goal and stretch goals. We had the must haves (stuff listed in the draft press release). We also had dozens of nice to haves we'd sneak in, time permitting.
Agile, Scrum, sprint style estimating is too fine grained, the horizon too near, to do effective estimating.