Chasing money is the least favorite job of every self-employed person - which is exactly why it gets postponed, and why unpaid invoices quietly pile up.
Script 1 - Day 1 overdue: the assumption of good faith
"Hi [Name], hope you're well! A quick note that invoice #[number] for $[amount] was due yesterday - here's the payment link in case it slipped through: [link]. Thanks so much!"
Short, warm, zero accusation. Most late payments are forgetfulness, and over 75% of late payments arrive within 14 days of the due date.
Script 2 - Day 7: the direct check-in
"Hi [Name], following up on invoice #[number] ($[amount]), now a week past due. Could you let me know when I can expect payment? If anything's holding it up, happy to help sort it out. Payment link: [link]"
Notice the question - "when can I expect payment?" - which requests a commitment, not just awareness.
Script 3 - Day 14: terms and consequences
"Hi [Name], invoice #[number] is now two weeks overdue. Per my payment terms, a late fee of [X] applies after [date]. I'd much rather not add it - can we get this settled this week? [link]"
Script 4 - Day 30: the final notice
"Hi [Name], this is a final reminder for invoice #[number], now 30 days past due. If I don't receive payment or hear from you by [date], I'll have to pause work / refer this to collections. I'd genuinely prefer to resolve it directly - here's the link: [link]"
The real fix is structural
Scripts recover invoices; systems prevent the chase. Due-soon reminders before the due date, automatic overdue nudges after it, a payment link in every message (never "mail a check"), and card-on-file auto-charges for recurring clients each remove a place where payment stalls.
Never write a chase email again
Ivy flags overdue invoices, drafts the reminder for you, and sends it after your one-tap approval. Due-soon and overdue nudges also run automatically.
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