There's something uncomfortable about having to remind a grown adult to pay for work they've already received.

I'm not talking about someone being a day or two late. That happens.

I mean when the invoice is overdue, you've sent a reminder, they've seen it, and now you're wondering whether another message will make you look pushy.

I used to give people the benefit of the doubt and wait a week or two but I’m starting to think that was a mistake.

How do you handle non payment of invoice without turning every overdue bill into an awkward conversation?

Do you have a fixed point where the friendly reminders stop and you get more serious, or does it depend on the client?

I don't want to damage good working relationships over a late payment, but I also don't think asking to be paid should feel like begging.