I'm bad at estimating

99 little bugs in the code. 99 little bugs in the code. Take one down, patch it around, 127 little bug in the code...

Wonder why we have trouble estimating...

i told my manager we were 2-5 days away from being done. that was 2 work weeks ago.

Chowder.io

My estimates reflect the quality of the request, often akin to the scribbles children make with crayons

That's why you got to Scotty the estimates, if you have to give one at all. Ideally break up work enough that nothing is off by a ton.