If it helps, anyone who asks me for help typically takes priority of whatever else I was doing, and I try not to belittle while helping others out.
With respect to heavy machinery and “winging it” I think the main issue is, the person who makes the mistakes doesn’t have the feedback loop to know they did something wrong. Not to pick on the person who messed up the above, but the collet being bent doesn’t harm their work, and the parallels being out of true didn’t matter for how they were using them. The next person who wants true parallels and a tight collet is the one that suffers.
Also, there is the cost associated with the mistakes, which in the machinist world is far too expensive for the lesson learned.
With all of that said, I do agree that some people may be afraid to ask for help with the perception of our attitude being, “you fucked up, so you’re banned forever”. We should be working to change that.