Watch What You are Saying, Idiom

Not sure if this is a new thing or a self revelation sprouting from my recent adventures (the more I use that terminology, the more exciting it becomes!). See if you can spot the pattern from just the last few days at work.
1) I was talking to my HR Director about employee evaluations I need to complete for my direct reports.  In an e-mail, I asked her “what’s my drop dead date?”
2) we have a data system that is difficult to navigate.  Yesterday, I finally almost built a custom report to pull out all the information I need, only to be derailed by, well, I’m not sure what.  I expressed my frustration to my two social work interns, who were in my office at my moment of maximum consternation: “this is making my head hurt.  Feels like my brain is going to explode.”
3) later the same day, I was talking to my Director of Finance about a monitoring report we just received.  While there were some issues, it wasn’t as bad as it could have been.  My response: “that certainly could have been much more of a car wreck than it was.”

I’ve even caught myself telling someone “let me put on my fundraising hat”.

Several, equally plausible things going on here:
a) I am peppering my speech with oblique references to my adventures to make sure everyone keeps paying attention to me,
b) it’s probably that first one

By the way, what-the-hell is the origin of using “drop-dead date” in a business setting?  Or any setting that’s not hospice?  And by the way #2, if your hospice service uses it, fire them.

And by the way #3 - I actually now want a fundraising hat.  It might very well be fabulous.