Send the invoice

And make sure you get paid

One of the biggest shifts a freelancer can make is realizing that professional habits matter just as much as professional skills. For example:

You have to send out invoices if you want to get paid.

This is both deceptively true and incredibly complicated, especially if you’re in the early parts of your freelance career. I say that with no judgment. As I’ve told people at our weekly co-working sessions, in my early years as a freelancer, it sometimes took me weeks to send invoices to clients.

Photo by SumUp on Unsplash

I’d finish a project, think about invoicing, and then put it off. Sometimes for a few days, sometimes for up to six weeks. This did no favours for me, and honestly, it didn’t help my clients either.

I can’t fully explain where the hesitation came from. I’ve never been especially good at discussing money, and nothing feels quite as aggressive, from a money perspective, as reminding someone that they owe you some. So maybe my discomfort around money was bubbling up every time I opened my invoicing software.

I also worried, deep down, that sending the invoice would somehow remind the client of something they didn’t like about my work. As if they’d see an invoice from me and think, “Oh yeah, we approved that article, but now that the invoice is here, we remember that one sentence we didn’t love and we’ll never work with her again.” Which, in retrospect, would make them exactly the kind of client I wouldn’t want to work with again anyway.

Sometimes, the actual work of creating and sending the invoice felt overwhelming. If I left invoicing until the last thing on Friday, sure enough, Friday afternoon would roll around and I’d think, “I’m too tired right now. I’ll do this Monday morning, when I have that fresh, start-of-the-week energy.” Reader, I almost never had that energy. So the invoices kept getting put off, like emptying the dishwasher or preparing my taxes.

Eventually, I’d end up batching invoices, which meant invoicing became a much bigger, more drawn-out process than it needed to be. And because it felt like a bigger process, I put it off even more. By the time I finally sat down to create the invoices, I’d often forgotten important details. I’d have to search my inbox for the purchase order number, the exact quote we’d agreed to, the payment terms (if we had negotiated payment terms), or whether the invoice was supposed to be in Canadian or U.S. dollars. Which, of course, made the whole thing take longer.

And so weeks would go by before I sent an invoice.

That delay didn’t make things easier for my clients, either. Many clients work with budgets, and once money has been allocated to a project, they often want to pay it and close the loop. They don’t necessarily want that amount sitting in their system for weeks while everyone moves on with their lives and new bills come due.

And, because many clients don’t pay on receipt of invoice — they have their own payment terms — waiting several weeks to invoice meant I sometimes wouldn’t get paid until more than two months after a project was done. Not great for my credit card, my cash flow, or my confidence.

Looking back, I realized it wasn’t just about the invoices, it was about avoiding the discomfort that comes with asking to be paid. The best way to deal with that discomfort is to set up systems that do the heavy lifting for you.

These days, I have a firm policy for creating invoices and following up on payment. It means I get paid much faster — I rarely wait two months now — and I don’t have to spend hours searching my inbox for crucial details I promised myself I’d remember.

Here’s what changed:

I use an invoicing system

Yes, my invoicing system costs about $50 a month. And yes, it’s worth it. The time and mental energy it saves me more than make up for the cost, especially because it removes so many energy-sucking decisions from the invoicing process.

My invoices follow a template, and I can charge in Canadian or U.S. dollars with the click of a button. Clients receive an email with the invoice, including a PDF if needed, and they can pay through the link, by e-transfer, or by direct deposit. I can also see the invoice history: when I created it, when I emailed it, whether it has been viewed, and whether it has been paid (if it’s paid through the system, it gets updated automatically, otherwise, I go in and mark it as paid when the money reaches my account).

That “viewed” feature is especially handy if a client says they didn’t receive the invoice after, in fact, viewing it three times. Not that this has ever happened, obviously. And if I need to make a change, I can edit the invoice easily.

Each client can have its own payment terms, tax settings, currency, and billing details. That means I don’t have to remember whether this client pays in 15 days or 30, whether they’re charged GST/HST, or whether the invoice should be in Canadian or U.S. dollars. The system remembers for me, which is good, because my brain is already busy remembering where I left my phone.

I write up the invoice as soon as the project is approved

Once I have approval in my inbox, I go straight to my invoicing system and create the invoice. I don’t necessarily send it yet. But I create it.

This is the step that has probably made the biggest difference. When the project is newly approved, all the details are still easy to find. The quote is recent. The purchase order number, if there is one, is usually in the latest email thread. The deliverables are clear. The client contact is obvious. I’m not trying to reconstruct the project from memory three weeks later while searching my inbox for “approved,” “rate,” “PO,” “go ahead,” and “I think we said $1,200?”

Creating the invoice right away also means the hard part is already done. When the project is finished, I just log into the system, review the invoice to make sure it’s still accurate, and hit send. No stress, drama, or detective work. I literally have no excuse not to send it right away.

I charge a deposit

Charging a deposit helps weed out clients who may not be serious about paying. It also smooths out my cash flow, which is not a small thing when you’re self-employed. But there’s another benefit: it forces me to create the invoice immediately.

The deposit is included on the invoice, so when the final invoice goes out, the client can see the amount already paid and the balance owing. I don’t have to do the math manually. I don’t have to remember what was paid when. I don’t have to create a second little spreadsheet that I will absolutely forget exists. The system handles it.

And because the client has already paid something, the final invoice feels less emotionally loaded. The payment relationship has already begun. I’m not suddenly introducing the idea that this work costs money. We both know it does, which we’ve acknowledged with that deposit.

I send the invoice immediately after submitting the work

This is my rule now: once the work is submitted, the final invoice goes out immediately. No putting it off until tomorrow or Friday or when I feel more organized energetic, or desperate for money. Immediately.

Sometimes, especially with new clients or those who take a long time to give feedback, I send the final invoice when I submit the first draft. That way, I’m not waiting months for revisions before the payment clock even starts. With clients I’ve worked with for a while — clients who pay on time and tend to have minimal revisions — I’ll often send the invoice after the final version is submitted.

Either way, the invoice goes out at the appropriate submission point. It does not become a loose end. Because loose ends are where invoices go to die.

I follow up before I’m annoyed

Perhaps a photo to send clients who haven’t paid Photo by Call Me Fred on Unsplash

This was another important shift. In the past, I’d avoid sending the invoice, then avoid checking whether it had been paid, then suddenly realize the payment was late, then put off following up until I was cash-strapped and resentful. Which meant my first follow-up came from a place of irritation.

Now, I try to make payment follow-up boring. If an invoice is approaching its due date, I check the status (and yes, my invoicing system tells me when payments are overdue). If the client hasn’t yet viewed the invoice, I’ll send a quick email to confirm they’ve received it, double-check the correct email to send it to, and offer to resend it if they can’t find it.

If it’s overdue, I send a polite follow-up.

Hi [Name],

I’m following up on invoice #[number], which was due on [date]. Could you let me know when I can expect payment?

Thanks so much,

[Name]

That’s it. I don’t over explain, apologize, or act meek about it. I simply remind them the payment was due.

Invoicing is part of the work

For a long time, I treated invoicing as something separate from freelancing. The writing and editing were the work. The thinking, interviewing, researching, revising, and polishing were also part of the work. The invoice felt like something awkward I had to do after the real work was finished.

But invoicing is part of the work. Following up on payment is part of the work. Having a system is part of the work. And reframing it as part of the work has helped me be more systematic about it. Sending an invoice isn’t an act of aggression or a test of whether the client still likes me. It certainly isn’t a rude interruption. It’s the administrative step that allows the business relationship to function. If they’re professionals, they should be expecting an invoice from me, not praying it won’t come (and if they are praying it won’t come, they probably won’t make for great repeat clients).

You did the work. Now the client needs the invoice so they can pay you for it. It’s that simple.

If invoicing feels weird, you’re not alone. A lot of freelancers struggle with this, especially early on. But you don’t have to wait until it feels effortless before you build a better system. You can make it easier while it still feels awkward. In fact, a better system will probably make the act of invoicing feel a lot easier.

Start small:

• Create the invoice as soon as the project is approved so you aren’t relying on memory.

• Send it as soon as the work reaches the agreed invoicing point.

• Use software, templates, or recurring reminders so you’re not constantly building from scratch.

• Follow up calmly when payment is late.

• Remember that getting paid is not a bonus part of freelancing. It’s the part that makes freelancing sustainable.

Your system doesn't have to look like mine. You might use accounting software, a spreadsheet, or even calendar reminders. The important thing isn't so much the tool; it's building a system that doesn't rely on you feeling motivated to do an uncomfortable task.

Every time you send an invoice promptly—even when it feels awkward or uncomfortable—you're reinforcing something much bigger than an administrative habit. You're becoming the kind of business owner who doesn't let temporary discomfort dictate important decisions. That's a capability you'll use far beyond invoicing.

Send the invoice. Future you will be very, very grateful.