I first heard about this in the context of software project estimation. The author (forgotten to me) made the point that nobody has permission to think about disasters when estimating project completion time. So why not explicitly ask them to? "So now we have our estimate, what would cause us to miss it?" And in the course of giant monster attacks, you give people permission to talk about specific scenarios that are…
The reason no one does this is because thr answer is constant "something might fail and add an arbitrary delay" once you hace committed to play the estimation game, you're committed to the delusion and reality checks dont matter. Just stop trying to estimate.
I'm sure my boss and customers will appreciate me saying "it takes as long as it takes", nothing will go wrong, it's clearly just that simple :)
Why not instead of working at all just earn a million a year off the interest from a well performing stock portfolio instead?