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> 1. You're not breaking down the work into small enough chunks to properly think about how long it will take

This usually means prototyping, which means actual coding, which means you couldn't do it as you already had to give your estimation. To put it another way, places who require estimates for planning want them during planning and don't allow time for doing this. On the up side, when they do let you take the time to prototype they take your prototype and put it right into production because then the estimate is 0.

> 2. You are probably consistently under (or rarely over) estimating and should be able to fix that. For me, I have to triple my estimates, it always takes 3 times longer than I think it would

This is a common trick but it really just means you are not really estimating, but guessing that it will take less than this amount of time. This would be more apparent if you gave an estimation range, what you actually estimated to your estimate times the 3X padding.



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