I think it's understandable why programmers dread doing estimates so much. But I believe there are multiple factors contributing to the current overall mess and the guilt should be shared among several areas -- and that includes us. Estimates are often, if not always, mistaken as commitments or deadlines. But we don't do a great job on explaining that estimates are probabilistic by nature, there are risks involved, a…
Ironically, I've recently been catching flak for "not being confident enough" when I give confidence intervals around my estimates indicating uncertainty.
In some sense, literally can't win. I then realized it was more about my lack of doing this: https://www.csun.edu/~to18470/articles/Managing_your_boss.pd...