I can't count how many times I've said "sure thing, boss. Can you send that to me in an email so that I don't forget?"
I do that alllll the time.
I can't remember if I sent it to her in writing, but I did say it in front of the entire company, including her son (it's a small family biz) who was behind her mouthing "YES! THANK YOU" to me for saying it.
She was in a similar situation to this before and the other party went bankrupt and she had to pull $50k out of her pocket to pay for something so that the conference would still happen ($100k+ annual profit on this conference, so it was a good investment to not let it fail). Now we are doing the same thing where this other party is supposed to pay a certain amount for this conference ($80k) and she is afraid she will get ripped off again somehow and have to pay the money. (There is zero reason to believe this would happen again.) So she wants to PREPAY the $80k out of her own pocket in order to... not give them a chance to rip her off by not paying it. But what she's actually doing is not giving them a chance to NOT rip her off. She's enforcing the worst-case scenario on herself.
And we keep going back and forth on it where I'll convince her that she shouldn't pay it (I mean, at least give them a CHANCE to pay it!) and then the next day she'll ask me to look over a draft and I see that she's written in a letter to them something along the lines of "I assume I'll be paying that $80,000 for the conference, so..." Why, why, why, why. Why? I mean, I know why. She has a hang-up after being ripped off a few years ago. But it is SO IRRATIONAL.