I guess I am the odd one out here, but I don't see this situation as awkward at all - I see it as you run a business and you need to act accordingly. When you are owed money, you need to communicate it ASAP. Preferably IN PERSON (no emails, no letters, no texts.... no miscommunications). "You still owe $_____ for your last week of vacation, if your fee isn't paid by ______ you will be charge a $____/day late fee." If it was an honest mistake, so be it. If they want to fight it, just let them know that you will see them in court. This is your business, nobody else is going to run it for you. Situations will only become awkward if you allow them to.

I make a point of clarifying in very specific detail the money aspects of my contract (though I do go over the entire thing) during interviews. I also make sure parents are completely certain they understand the contract they are signing so that there is no room for misinterpretation or "Oh, I didn't read that part of the contract" later on.

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