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Given a large task to estimate...
Break the task down into a complete set of smaller tasks.
Forces you to think deeper about what's really involved
These smaller tasks are boolean. They are either done or not done.
There is no "85% done" with a mini-milestone.
Estimate those tasks.
Few minutes to half a day in length, max
If you think it will take longer, break it down into smaller pieces.
Add them together and that's your estimate.
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