When did estimates turn into deadlines?

My technique is to give an estimate with error bars. Something like 6 weeks plus or minus 2. That then leads into discussion as to what is unknown/undefined leading to the uncertainty. Sometimes the error bars are larger than the estimate because I know there will be endless feature creep and UI revisions for something like "analytics". And sometimes the number could be negative like 6 weeks plus or minus 8. That is when the functionality already exists (eg the data is already there - you can already load it into Excel and a pivot table) and could be sufficient.

At my very first job out of college,¹ the VP who led the division that I was part of invited me into his office (I think there was someone else from the team, but this is 34 years ago so who knows) and talked about a little game he had encountered about estimates. He gave us a list of 20 things to estimate with 95% confidence (the only one I remember was the weight of a 747), all given as a range. If we did it right, we would get 19 of the 20 correct. The point was to set the range large enough that you could be confident about the answer.

I kept that as a practice when I did freelancing work, always giving my estimates as a range rather than a single number. It would be nice if agile(ish) practices incorporated this in the estimation process.

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1. Technically, my second job since I had a short temp job doing some cataloging work at a local used bookstore between leaving school and starting at that company.