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holding alarm clock to invoice on time

Avoiding Project Failure: Invoicing on Time

Eddie Carrillo
Eddie Carrillo

While it may not be the first thing that comes to mind when trying to stay organized as a freelancer or business owner, invoicing on time is a key component of effectively managing your business and maintaining strong client relationships.

As humans, we often overthink the small things—like when to invoice. Should I wait a few days before sending it? Should I send it with the completed project? Are Tuesdays better than Wednesdays?

But it’s important to remember that you have the right to get paid for your work. It’s possible that your client has a methodology they prefer when it comes to billing. However, make sure you have this conversation early on so as to avoid headaches when the time comes to receive payment. Waiting too long to charge a client can potentially lead to misunderstandings, confusion, and a ding to your reputation. So how do we avoid this?

Strategies for overcoming common doubts and questions about invoicing on time

Let’s go over some questions that freelancers deal with when invoicing, and how to navigate potential solutions.

Is one day better than another for sending an invoice?

No. I remember once debating if I should send an invoice on a Friday or wait until Monday. My thought process was that it might be annoying for my client to receive an invoice right before her weekend. But this was a classic case of overthinking. When sending an invoice, the day is not important. What’s important is having communicated with your client what works for you both.       

Should I wait for the client to bring it up? 

No. Most clients aren’t going to rush into how and when they can pay you, but if they hired you, they are more than happy to pay you. That’s why you’re there. Bring it up earlier rather than later—this sets you off on a positive, transparent note.

Recommended language:

  • “I generally invoice my clients the same day I deliver the project. This helps me better manage my bookkeeping. Does this work for you?” Using the word “generally” will give you a voice of authority – here, you communicate that you have a standard way of operating with clients but you leave the door open in case they have another way they’d rather pay.

Should I write new invoices for every project?

It depends. If you have a client who gives you repeated monthly work—a “subscription client”—it’s likely more convenient to send bimonthly invoices, like on the 1st and 15th of every month. This way, you charge for any projects delivered in the two weeks prior, and you and your client are constantly on track with the cyclic payments. Just be sure you include each item separately on the invoice so the client knows exactly what they are paying you for. On the other hand, if it’s not a subscription client, it’s best practice to invoice for each individual project.

Bottom Line

When we think of project failure, it’s generally screwing up the content or missing a deadline that comes to mind. But don’t forget that you aren’t doing work for free, and invoicing on time is what will get you paid.

I’ve heard nightmare stories about freelancers who are fearful of approaching their client about invoicing because they’re uncomfortable with discussing money. This leads to worry about their financial situations because they aren’t getting paid as often as they should be.

Talking about money as a freelancer is normal. You’re operating a business, and it’s a part of your job. Engage early in the invoicing conversation with your clients. This will not only help you ensure financial stability, but it will also show your clientele that you’re a confident professional effectively running a valuable business.


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