I remember reading of a name for the type of quantity that you always underestimate, even when you know that it is the type of quantity that you always underestimate and so allow in your estimate for the fact that you will probably underestimate. I have a feeling it was coined by Martin Gardner. Or at least written about by him. I can’t seem to google it.
I’ve tried to read G.E.B. several times. Never got as far as that aphorism. But, and I take full credit for this, I did coin that phrase myself, and I use it in my courses all the time. I call it Rule #1. I teach in the College of Education, and it refers to pretty much anything a teacher plans.