I see what you were going for. It was an attempt. The delivery could use some work. The joke itself may need a complete rewrite to be a different joke, but it might be salvageable.

When you hit rock bottom, know when to stop digging, and when to get a shovel.

For my part, I’ll admit that the setup wasn’t very good. I was trying to be the straight man foil to your bit to the degree I felt your comment permitted, as I’m not “in on the joke,” as it were, at least I wasn’t in on it then. I think HN is a hard venue to do comedy well, as you have to read the room over longer than a single comment thread or post. Your comments were already pretty deadpan and dry, so I think many couldn’t even see it as distinctly humorous rather than snarky or sarcastic or even unfunny if they viewed it as against HN guidelines.

https://en.wikipedia.org/wiki/Straight_man