My invoice is not paid and I'm tired of sending awkward reminders
I opened my accounts this morning and there’s nearly $11k sitting in overdue invoices.
I run a small commercial photography business in Pennsylvania, mostly working with real estate companies, restaurants and local brands. The work gets delivered on time, invoices go out the same week, and then somehow getting paid becomes another job entirely.
My current system is basically:
Invoice due.
Wait a few days.
Send a polite email.
Wait again.
Send another email that’s slightly less polite.
Eventually text or call and have that awkward “just following up on invoice #…” conversation.
It works eventually, but I hate how much time I spend doing it.
I’m wondering if I need a proper system that automatically changes the tone or frequency of reminders as the invoice gets older.
Something gentle when it’s three days overdue, firmer at two weeks, then a final notice if it keeps dragging.
How are you handling this without personally chasing every invoice not paid?
At this point I’d happily automate the uncomfortable part.