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I made a small system for estimating. Give 3 estimates. 1 lowball (if things are easier than expected). My actual estimate based on intuition. A high estimate (if nothing went right). Then my base estimate is the average of these. From the average I add 1 standard deviation (from the 3 estimates) of time for every degree of significant uncertainty.
This approach has worked out ok for me so far 
riekena25754yI hate when you give an estimate, a release date gets announced to the clients, then you are forced to release unfinished covfefe.

JS96183074ytrue...
 When do you think it will be ready?
 In a few days, max 1 week.
...after 3 weeks...
 It's almost ready... I will send you it next week. 
Don't estimate in time. Estimate in story points or t shirt sizes if you are very uncertain. People are.much better at relative estimations than absolute.

@CodeMasterAlex the idea about tshirt sizes is great! I haven't heard it before!

Newmaker0614y"We won't define a time estimate. We'll leave the time estimate open, but when we reach it, we'll double the time estimate" Dilma Rousseff

Kryptic694y@codetinkery If you estimate time like that would't your actual estimation almost always be the result of average of those?
Ex:
(low estimate + mid estimate + high estimate) / 3 = mid estimate(roughly)
Hrs:
(1+2+3)/3=2 
@Kryptic The base estimate is always the average, yes. However, I calculate the standard deviation based on the 3 estimates and add that to the average once, for every degree of significant uncertainty.
http://imgur.com/ze5uRiE
"low" uncertainty means "use the average value"
mid is 1 deviation.
high is 2 deviations.
and here is the code used to calculate the estimates: https://pastebin.com/0F4y2gRK
Do note that "standard deviations" are more precise the larger your dataset.
I've found however, that my "low estimates" are always too short, so the "average" number is more often than not closer to the "real low" while the high estimate lands somewhere near the uncertainty groups. 
@seeker it definitely sounds quite appetising if we name this the "pi coefficient"
welcome to devRant!
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