[mc]

Nice write up.

Want to add two other reasons we're horrible at making estimates.

1. Expectations. 2. No widely accepted language for writing requirements.

Re: 1. Expectations are just hard to manage. Even when you do get "So the site's pretty simple" - the set of features in their brain is totally different from the set of features in your brain. Alas, it'll take more than "all it needs to do is X, Y, Z" to fix this process.

Re: 2. Is there a professional software consulting company that has solved this problem? I say there isn't. I also say that with the advent of Agile/Lean Startup methodologies, it'll probably never happen - "No, we don't write reqs, we have stories you need to approve." uh huh, okay. For writing requirements, I got really damn fond of Cucumber, but then the lean-ux took off, and that shifted everybody's priorities.

Bottom line, until there's a widely accepted way to communicate design and functionality, making bad estimates will always be easy to do