It’s the same cycle every month. Payment terms are 30 days, but I end up waiting 60-90 days, constantly following up.
Makes me question whether this steady income is really worth the endless cash flow stress and those uncomfortable reminder emails.
Stop working for them until they catch up on what they owe. Simple as that. Tell them all outstanding invoices need to be paid before you do another hour of work. Most will either pay up quick or show themselves out. Either way you win. I learned this the hard way after carrying one client for four months of unpaid work.
Had a client who was always late, like 75 days every time. Same story - they promised money was coming, but nothing.
I started charging a 2% late fee after 30 days, and another 2% every 15 days after that. Most clients got their act together pretty fast.
As for that chronic late payer? They complained about the fees but kept paying them. I made an extra $400 from late fees that year.
Eventually, they found someone cheaper who didn’t charge fees. Honestly, good riddance. That constant stress isn’t worth it.
Been there with repeat late payers. Here’s what worked for me:
- Switch to shorter payment terms - go from 30 to 15 days
- Ask for partial payment upfront - even 25% helps with cash flow
- Set a firm boundary - after 60 days late twice, they’re done
The steady income isn’t really steady if you’re always chasing it. I dropped two clients last year for this exact reason and honestly felt relief more than anything.
You can probably replace that income with better paying clients who actually respect your terms.
Sometimes it’s just not worth it. Find clients who pay on time. Your peace of mind matters.
One last notice with a late fee might get their attention. Make it clear it’s their final chance.
If they still don’t pay, let them go. You need to focus on business, not chasing payments. Those long waits hurt your cash flow.
I just ask for half upfront now.