Have a retainer client, 9 months in. Invoices on the 1st, due net 15. Out of 9 invoices, 7 have been paid late. The shortest delay was 9 days. The longest was 42.
Every time I follow up I get a polite apology, a payment within 24-48 hours, and a vague promise it won't happen again. It always happens again.
The work is good. The relationship is fine. They are not in financial distress as far as I can tell. They just don't prioritize paying us.
I have tried gentle reminders 3 days before due. Tried a polite "your invoice is past due" email day 16. Tried calling. Tried a late fee clause in the contract that I have been too soft to actually enforce.
What I am wondering is whether there is a structural fix here that doesn't involve being aggressive. Auto-debit. Prepaid retainer. Smaller more frequent invoices. Or whether the real answer is to just enforce the late fee or end the relationship.
For folks who have had this exact situation and fixed it — what worked.