Send the invoice the day the work is done

The follow-up email is a genre. You write a draft. Delete the first line because it sounds angry. Add “just circling back.” Hate that more. Send it anyway, on a Friday, which is the wrong day, then check Stripe like it’s a slot machine.

I’ve written that email. A $2,400 site. I handed off the files on a Tuesday. I sent the invoice eleven days later because I was waiting until the folder felt finished. They paid on day 47. The work took sixteen days. Getting paid took forty-seven. The extra thirty-one were the due date I didn’t print. $2,400 sitting eleven days before I even asked is $218 a day I had already earned. I did that arithmetic in the same sitting as the eighth draft of “just circling back.” The awkwardness was not their personality. That’s on me.

I named a year of files after the month

Your name. Theirs. INV-041, not “for the website.” A due date, on the page, not in a later email. How to pay. Sequential numbers are how you prove a bill existed when someone says they never got it. I still have a year where I named files after the client and the month. Tax season was a scavenger hunt through Downloads. The page matters too — letterhead, one link instead of a PDF buried in a design thread, a separate email to AP — but this note is about when you send it, and what you do when the date passes.

Put the terms in the scope, not at the end

A lot of us accept Net 30 because it sounds grown-up, and then we suffer it. If rent is on the 1st, write Net 15 or due upon receipt in the scope they already said yes to. Inventing terms at the end of the job is a surprise. Surprises get paid slowly. Sometimes they get a “can we do 50% now?”

Send the invoice the day that slice of work is done. Waiting until it “feels finished” is how you train people to pay you whenever.

Split the bill where the work splits

“The day the work is done” is easier when the job has more than one day. On anything longer than a couple of weeks I invoice in slices that match the scope: a deposit before I start, a milestone when the first real deliverable is approved, and the balance on handoff. Each slice has its own number and its own due date, written into the scope before the job starts, so none of them is a surprise when it arrives.

• Deposit: 50% of the fee, due before work starts. I start when it clears.
• Milestone: 25% when the homepage is approved.
• Balance: 25% on handoff, Net 15.

The deposit does the most work. A client who pays half up front has decided the job is real. A client who can’t find the card for the deposit will not find it for the balance either, and I would rather learn that before the work than after it.

Make paying the easiest thing on the page

Most late invoices are not disputes. They are friction. The person who approves the work is not the person who pays, the PDF is in a thread they are not on, and the bank details are a paragraph they have to retype. Every step between “I should pay this” and “paid” is a place for it to stall. One link, a card option, and bank details on the same page remove most of those steps. A link can be paid from a phone between meetings. A PDF someone meant to forward waits until they are back at a desk, and then it waits behind everything else.

Watch the dates, not your mood

I used to decide when to follow up by how anxious I felt. Now I look at two dates: when the invoice went out, and when it was due. If the gap between the work being finished and the invoice going out is more than a day, that is mine to fix, not theirs. If the gap between due and paid keeps growing with one client, that is a conversation about terms on the next job — a bigger deposit, shorter terms — not a fourth follow-up on this one.

The three notes, so you don’t write a fourth

I keep a reminder on the due date. I do not invent a new personality for each follow-up. The text is almost always the same.

1. One business day after the due date: “Invoice INV-041 was due yesterday, $2,400. Link’s here. Tell me if you need anything on your side.”
2. A week later: “Checking in on INV-041. When should I expect it?”
3. Two weeks: “New work is paused until INV-041 is paid. Happy to restart the same day it clears.”

That last one feels rude until you notice you are the only person in the arrangement working for free. You already did the job. The date was on the page. Friday is a bad day to send any of this — AP is not processing you at 4pm. Monday morning. Then close the tab.