Been chasing an overdue invoice for three months now. Started friendly, got progressively firmer, but still trying to keep things professional since they might have future work.
Wondering how others handle that awkward middle ground between being persistent about payment and not completely burning bridges. The line feels really thin sometimes.
Send a clear deadline. Don’t waste time anymore.
Three months is too long. Set a clear payment deadline. After 30 days overdue, I apply late fees. At 60 days, send a final notice stating legal action may follow in 10 days. Then follow through.
Clients who don’t pay aren’t worth keeping. Those with future work will respect your boundaries.
Had this exact situation last year with a client who owed me for two projects. What worked for me was switching from email to phone calls.
Sometimes there’s actually a real issue on their end:
I called and had an honest conversation. Turned out their main contact left the company and nobody knew about my invoice. Got paid within a week after that call.
If the phone call doesn’t work or they keep making excuses, then you know where you stand. At that point the relationship is already damaged anyway, so might as well get your money.
Don’t let it drag past four months though. I learned that lesson the hard way with a different client who just kept stalling.
I used to stress about this too until I realized something. The clients who actually have future work lined up don’t let invoices sit unpaid for three months.
What I do now is give them one more chance to explain what’s happening. Send a message saying you need to understand their payment timeline because you’re planning your next steps. Give them 48 hours to respond.
If they ignore you or give vague answers, that tells you everything. Real clients with real future projects will give you actual dates and follow through.
I’ve only had one client come back with legitimate future work after a payment chase that long. And honestly, working with them again was still a headache because they had the same payment issues.
The bridge is probably already burned if they’re comfortable ignoring you for months. Might as well get paid for the work you already did.
Chasing payments can be a hassle. If you’ve tried firm reminders, it might be time to let it go.