Lumifer comments on Visions and Mirages: The Sunk Cost Dilemma - Less Wrong
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That is the core of your problem. Since it's happening repeatedly, you should stop assuming that you know the distance to completion and assign a probability distribution to the number of step (or time) needed to get the project done, likely with a long right tail.
If you constantly encounter the unexpected, you should acknowledge that your expectations are faulty and start to expect the unexpected.