The awkward conversation every freelancer avoids (and how to have it)

Source: Dev.to

The money conversation

Not the “here’s my rate” one. The other one. The one where your invoice is three 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 we avoid it

• 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 five‑minute conversation.

All of which is completely irrational—and completely normal.

Turning “chasing payment” into a 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 two 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 seven days, I’ll begin formal recovery proceedings.”

Day 28

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.

Note: Clients who pay late usually aren’t trying to scam you. They’re often just disorganised, have a slow accounts team, or simply forgot.

A clear, consistent process fixes about 90 % of late‑payment issues before they become disputes.

Free tools that helped me

• 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.

Share your experience

What’s the most overdue an invoice has ever been for you? Mine was four months. I got paid in the end, but only because I stopped being polite about it.

Drop your horror stories below 👇