Getting paid on time, without being weird about itGetting paid on time, without being weird about it

I love drawing. I don’t love chasing invoices. For my first few years I was bad at it in the way most freelancers are: too polite to ask, then too annoyed to ask nicely. These days I almost never chase anyone, and it’s not because my clients got better. It’s because my paperwork did.

Half up front

Every project starts with a deposit: half the fee, paid before I draw anything. It isn’t about trust. It’s about commitment on both sides. A client who has paid a deposit turns up to meetings, answers emails and gives feedback on time, because they’re invested too.

I used to be shy about asking for it. Then I noticed that nobody else is. Builders ask for deposits. Wedding photographers ask for deposits. The bakery asks you to pay before you eat the croissant. Nobody thinks they’re being weird.

For bigger jobs I use thirds instead of halves, but the first third still arrives before the first pencil.

If a client won’t pay a deposit, I take that as useful information. It usually tells me how the rest of the project would have gone.

Milestones you can see

The rest of the fee is tied to milestones, and each milestone is something the client can see: the approved sketch, the finished character, the delivered files. Not “week three”. Not “when it’s done”.

Visible milestones make the invoice feel obvious. When the client is holding the finished turnaround sheet, the invoice for the finished turnaround sheet doesn’t need explaining.

I send each invoice the same day the milestone is done, while the client is still pleased. An invoice that arrives three weeks later feels like a surprise, even when it isn’t.

Fourteen days, written down

My payment terms are fourteen days, and they’re written in three places: the proposal, the contract and the invoice itself. Not thirty days. Not “on receipt”, which nobody takes seriously. Fourteen days is long enough to get through a finance team and short enough that nobody forgets.

The invoice also uses the name the client uses for the job, not mine. My files say “bakery mascot v4”. Their accounts team knows it as a purchase order number. If the invoice has the number, it gets paid. If it has my file name, it sits in someone’s inbox, wondering who I am.

don’t apologise in an invoice email. you did the work. it’s a receipt, not a favour.

Contracts don’t have to be scary

None of this works without a contract, and mine is two pages long. It says what I’ll make, how many rounds of changes are included, when each payment is due, what happens if it’s late, and who owns what once it’s paid. That’s it.

A short contract gets read. A long one gets signed without being read, which helps nobody. I send mine with the proposal, in plain language, and I invite questions. Clients have changed things in it, and that’s fine. The point is that we both know the rules before there’s any money to argue about.

The friendliest overdue email I know

Sometimes payment is late anyway. Usually it isn’t personal; it’s a busy inbox. So the first reminder is short and warm, and it goes out the day after the due date:

1. A subject line with the invoice number and the word “reminder”, so it can be found.

2. One line: “Just a nudge that invoice 041 was due yesterday.”

3. The invoice attached again, so nobody has to search.

4. One line about the work, something true and kind, because people pay faster when they remember why they liked you.

5. “Thanks so much”, and nothing else.

That email has worked every time I’ve sent it. If it ever didn’t, the second reminder a week later would be the same email with one more line: the date the late fee from the contract starts. I’ve never had to send a third.

The least fun drawing I do every month.

Small jobs count too

The rules don’t change for small jobs. A single spot illustration gets a deposit, terms and an invoice with the right number on it, just like a mascot. Small jobs are where bad habits start, because it feels silly to be formal about a few hundred euros. It isn’t silly. It’s exactly the same work, just shorter.

When to put the pencil down

The last rule is the one that took me longest to keep. If a payment is more than two weeks late, I stop working on that project until it’s paid. I say so politely, and I say it before it ever happens, in the contract.

It feels dramatic the first time. It isn’t. It’s just the order things happen in. Clients who pay late usually aren’t bad people; they’ve simply been allowed to. Being clear early is kinder than being cross later, and it means I can get back to the part I actually like.