The money conversation.
Not the "here's my rate" one. The other one. The one where your invoice is 3 weeks overdue and you're drafting your fifth "just checking in" email while silently seething.
I've been there. Most freelancers have. Here's what I've learned about why we're so bad at this, and what actually works.
Why chasing money feels awful
- We confuse being professional with being passive
- We think asking for money we're owed is somehow rude
- We're scared the client will think we're difficult
- We'd rather lose £2,000 than have an uncomfortable 5-minute conversation
All of which is completely irrational. And completely normal.
The framework that changed everything for me
I stopped thinking of it as "chasing payment" and started thinking of it as "process."
Day 1 (due date): Automated reminder goes out. Not me being pushy — just the system doing its thing.
Day 7: Friendly follow-up. "Hi, just flagging invoice #X is a week overdue. Can you confirm when payment will be processed?" No apology. No "sorry to bother you." Just facts.
Day 14: Firmer. "This is now 2 weeks overdue. Under UK law, I'm entitled to charge statutory interest at 8% + base rate. I'd prefer we resolve this without going down that route."
Day 21: Final notice. "If payment isn't received within 7 days, I'll begin formal recovery proceedings."
Day 28: Actually follow through. Small claims court costs £35-£455 depending on the amount. You don't need a solicitor. I've done it. It's not fun but it works.
The secret nobody tells you
Clients who pay late usually aren't trying to scam you. They're just... disorganised. Or their accounts team is slow. Or they forgot.
A clear, consistent process fixes 90% of late payment issues before they become disputes.
Some stuff I built
Because I got tired of rewriting the same emails:
- Payment reminder generator — picks the right tone based on how overdue the invoice is
- Late payment interest calculator — shows exactly what you're legally owed
- "Should I chase this invoice?" tool — gives you an action plan based on the specifics
All free, no sign-up needed.
Honest question
What's the most overdue an invoice has ever been for you? Mine was 4 months. I got paid in the end. But only because I stopped being polite about it.
Drop your horror stories below 👇
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