I’ve freelanced for more than a decade now, and I can still remember the first time I had to follow up on an unpaid invoice.
My stomach sank.
I refreshed the email too many times. I wondered if I had done something wrong.
Luckily, it turned out to be an honest mistake, and it was resolved quickly.
The second time?
A payment platform switch messed everything up, and once again, it wasn’t intentional.
But I know a lot of freelancers aren’t so lucky.
Some have had to chase invoices for weeks… months… sometimes even longer.
So I wanted to know how other freelance writers and copywriters handle late payments.
I pulled their insights together so you have a reference when a client drags their feet.
Here are the smartest, kindest, and most effective ways freelancers are getting paid in 2026.
1. Create a Fake Employee (Or Use a Tool)
These approaches rely on structure, automation, and emotional distance, something freelancers desperately need when money’s involved.
Here is what Mallorie Wilson has to do if she has late invoices that haven’t been paid.
“I made up a fake accounting manager named Mike and I found that when Mike handled my invoice payments, they were paid on time and if any were late no-one disputed the late fee. I also automated my invoices with a 1 week reminder, 3 day reminder, and day of reminder. Every client receives it no matter what and they can reach out to Mike anytime if they are going to have an issue or need additional accommodations.”
It works because clients treat “Mike” with more urgency than “the freelancer.”
Kelly Zimmerman uses a tool that takes the guesswork out of deadlines and fees.
“I’ve implemented an invoicing system for freelancers (Moxie) that allows you to set a payment deadline and can automatically add a late fee to the invoice for late payments (which the client can see upfront).”
Automation = clarity = fewer uncomfortable conversations.
Eleanor Bryan takes the “fake employee” strategy up a level.
“I’ve created a separate email account for a fake employee called “Jonathan.” Companies are happy to ignore my requests for payment as it’s obvious I’m a sole trader, but as soon as “Jonathan from accounts” emails them they think I’m a bigger company and they pay up.”
Remi Audette agrees to give your boundaries a name.
“Have an accounts email and a “pushy bookkeeper” called Debbie – she doesn’t have to actually exist. She just likes invoices being paid on time and will let clients know! Helps to remove the emotion out of it for you, because you’re not you, you’re Debbie.”
2. Protect Yourself With Upfront Payments, Milestones & Contracts
Rebecca Whitlocke invoices before doing any work. This is a great strategy for long term project or big projects.
“I invoice in advance – never had any clients dismiss it. Usually a friendly reminder gets the message through. Here in France we can charge €40 per invoice + a % of total invoice for late payment which is passed on to the client as late payment fees, it’s on every invoice I send.”
Clear, legal, written terms prevent chaos later for Rebecca.
Stephanie C. Watterson keeps the negotiation fair and structured.
“I have had to start asking clients to pay 50% up front and 50% at the end of our agreement. That said, I be really transparent about late fees in my conversation with clients and in emails too. I also keep following up on email too. Being a pest is worth the money, perhaps…”
Sarah Griffin doesn’t wait for red flags to grow. Instead she stops working.
“With new clients, I don’t do a huge milestone without pay; I expect some up front and regular payments. For regular clients, I express my terms – payment within 5 working days. I’m a freelancer, not a huge company! I’ve not had problems with payment because I trust my gut. And if I didn’t get paid, then they don’t own that work and can’t use it. I do not go easy on non-payers or scope creeps. STAND YOUR GROUND! (but try and avoid it in the first place). ”
Sarah A. reminds us that contracts aren’t optional.
“Just weighing in on late fees. State laws vary widely on these, with mandatory waiting periods, caps on fees, etc. When invoicing or setting up contracts, you may have to accommodate the laws in the state where your client is, too. And in almost all instances, late fee structures must be agreed upon in writing. In some cases, you may also have to follow a more formal “collections” process when sending out past due balance notices or taking other steps to collect past due payments.”
This is critical, especially if you work across borders.
3. Be Proactive
Joni Sweet tackles late payments before they become late.
“If a client has historically paid me late (or if it’s a new client, and I’m worried they might not be super on top of things), I usually send an email a week before the payment is due with a friendly reminder, and asking if there’s anything else they need from me to make an on-time payment. I’ve found being a little bit proactive can really help prevent late payments. ”
A gentle nudge beats a stressful chase.
Meenakshi Lohani has a detailed list making this practically a masterclass.
“Set mini-deadlines: Instead of “pay me whenever,” give clear expectations: “Payment due within 7 days of invoice.” Humans respond to clarity.
Offer a simple way to pay. Include direct links or options: bank transfer, Stripe, PayPal. The easier it is, the faster you get paid.
Call when emails fail. Sometimes a 2-minute phone call does what three polite emails can’t. Keep it casual: “Hey, just following up on the invoice — is everything okay on your end?”
Document everything. Keep a quick log: invoice sent, reminders, responses. If things go south, you have a clear timeline.
Use a calendar ping. Schedule follow-ups the moment the invoice is due. Don’t wait for the client to remember. Treat it like an appointment you can’t miss.
Clients usually pay faster when you make it easy and non-threatening.”
This is how freelancers make their process feel “official”—even solo.
4. Persistence Pays (Even When It’s Uncomfortable)
Mathew Klickstein’s honesty is refreshing.
“Persistence is key. I’ve been told (sometimes even by friends and family) that I text, call and/or email too much. I always appreciate that feedback and there are honestly times where I’ll restrain myself if it’s someone who is just outright saying, “Matt, enough. Just stop.” Prefer that to ghosting. Behavior that I can respect, because it means I’m dealing with a person who is honest and let’s their feelings be known. But … if it’s someone who owes me money? Oy vey: I don’t stop until it’s done. I’d rather their being put off or a little upset at me but I get my money than simply hanging back out of some kind of propriety or politeness. No. They’re the ones with the money and the power, and I gotta go for it until it’s done. Chasing people down for money is awful. But it’s just something we have to do these days, or else we’re doing work for nothing. So, I say persistence is key. Even beyond what you’d normally feel comfortable with.”
He’s right, politeness should never cost you income.
5. Use the “External Authority” Strategy (It Works Every Time)
Brooke Turbyfill uses taxes as a conversation starter.
“I have used taxes as a way to get a client’s attention and remind them that payment is required in a subtle way. It has worked every time, and at the end of the day, it was usually an honest mistake or an accountant who was swamped. So, patience, kindness, and clarity go a long way.”
Melanie Lockert also leans on the accounting angle:
“Whenever I’ve had this issue, the most effective strategy is to say that my accountant noticed an outstanding payment and would like to wrap up my books for tax purposes. Making it about my accountant and the IRS seems to deliver more urgency. ”
Clients suddenly respond when they think something official is happening.
6. Be Willing to Escalate
Kirsten Lamb’s advice is simple.
“Don’t be afraid to tell them you will escalate. Make it more problematic for them to not pay you than to pay you. That aside, always assume the best of intentions. It’s often an honest mistake or a glitch on their side, assume best intentions until it’s clear they have no intention of resolving things honestly.”
Escalation doesn’t require aggression, just structure.
Helen Iatrou takes the practical route for late invoices.
“I’ve also been very lucky in terms of being paid on time. I’ve rarely had to chase a client for payment. However, what I would do, if needed, is notify that I’ll be pausing all future work until payment is made. ”
When work stops, payments start moving.
Shari Berg is structured and persistent.
“I send 3 total notices – the original invoice, a follow-up, and a last-chance notice. If I’m still not paid, I file in small claims court to collect what is owed if it’s an amount that makes it worth suing over. And sadly, I’ve had a few of those. ”
For some invoices, that’s exactly what you need.
Juliet John’s story is proof that escalation works.
“My best advice is to threaten to out them on LinkedIn. I once chased an invoice with a well known company for about 5 months. My POC stopped responding to emails for no reason. I would follow up and follow up for weeks without any response. Whenever he wrote back, he would say we are working on it and this was for just $500. One day I got fed up and told him I it was my last civil email, the next time I would cc his CEO and call him out on LinkedIn. I added the CEOs email so he could know I was serious. He responded in hours, looped accounts in and my invoice was paid that week.”
Sometimes you need leverage, even just the threat of it.
You’re the Boss!
When you’re new to freelance writing, you’re not thinking having late invoices or how to handle difficult clients.
At least that was me when I first started. It was all rainbows and unicorns and BEST clients ever!
But then it happened to me and I had to quickly learn how to deal with late invoices.
I know it’s easy to assume you’re doing something wrong or that following up will make you seem difficult.
But the truth is simple: you’re the boss. You run the business.
You set the expectations.
And you deserve to be paid for the work you’ve already delivered.
If an invoice becomes late, the best thing you can do is follow up right away.
A short, clear message sent the day after the due date keeps the process professional and avoids unnecessary stress later.
It’s not emotional, it’s not confrontational, it’s just part of running a business.
Most of the time, the issue really is something simple, like a missed email or a busy accounting team.
Starting from that assumption helps you lead with confidence instead of frustration.
And sometimes the healthiest choice is to move on.
A client who consistently pays late isn’t a long-term fit for your business, no matter how nice they are or how good the project looks on paper.
This is something I do with difficult clients for sure! I just cut ties and move on.
I can go creates space for clients who value my work and honor my terms.
Every time you follow up, hold a boundary, or stand firm on payment, you build confidence in your business.
You’re not bothering anyone. You’re not overreacting. You’re running a professional service—and acting like the boss you already are.
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