I had a great boss (founder of the company) who said, after I just screwed up, "There is not a mistake you can make, that I haven't already made. Just don't make the same mistake twice."

Reminds me of the boot-camp story of the nervous recruit inquiring of his sergeant:

"Sir beg my pardon for asking but why did you give Smith 50 press-ups for asking a question? You said that there were no stupid questions. Sir."

"I gave him the press-ups the SECOND time he asked. Will you need to ask again?"

That's awful. So they train people to never ask for clarification or refresh if they misunderstand or forget, so instead they go on to make a far worse mistake acting on incorrect information.

A clarification question is not asking the same question twice. The point seems to be that you should pay attention.

I believe that is the lesson from the story, but I don't believe the lesson from the story == the lesson irl.

The IRL takeaway is that if you don't open your mouth, you don't get punished. If you do open your mouth, you might get punished.