I was reading this just now – Why Can’t Developers Estimate Time? – and realized the discussion leaves out some fairly important psychological factors that influence time estimates significantly.

As the developer, you focus on the risky bits — the parts that are technically difficult & complex, that use new APIs or new libraries you aren’t familiar with, that require designing a new UI, or matching very strict performance tolerances.

For these sections, developers (with a little training) can learn how to estimate as well as possible — it’s hard, we know it’s hard, and either we’ll say “that’ll take a long time” or we say “we’d better do a proof-of-concept first, because I’m not sure at all how that will go.”

Now we get to the rest of it — the trivial parts. Writing some simple tests, taking input, validating it, storing it, returning something else simple straight out of the database… it’s simple, it’s boring, and any developer on the team could do it.

But it always takes an embarrassingly long time (with the emphasis on “embarrassing”).