How often should I be invoicing? + Getting monthly payment gigs

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I wish being a freelancer just meant creating innovative and thought-provoking work all day.

That’d be fun, right?

Unfortunately, If we want to create a business out of doing what we love, at some point or another we’re going to have to focus on the “business” part.

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“Invoicing” is such a boring word… But let’s attempt to rebrand it. Think of invoicing not as a means of billing your clients, but as a means to set up a predictable and stress-free business model for yourself.

If you master this part of your business, you’ll be able to maximize your time spent working on the creative part (which is the most important part of your business after all).

There is an element of sexiness to having money flow in every week. Maybe even multiple times per week, depending on how many clients you’re juggling, but think about what comes with this:

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More emailing. More sending invoices. More correspondence. More paying a book keeper (if you have one). More follow up emails… Where would you find time to do the work?

When it comes to freelancing, the fewer invoices you send, the better.

Before you look away from this article, let me apply some context to that statement.

Some tend to think that the more frequently we receive payment, the less stressful our lives will be. Others tend to rely on a monthly payment schedule as the golden rule. There are puts and takes to both, and both can be relevant depending on the project at hand.

For example, I have two long-term clients with ongoing maintenance work. In a given month, I may work 6 hours or I may work 120 hours. I benefit greatly from a monthly invoicing agreement, by which it is dictated in my working agreement, that I will send a monthly invoice and they agree to pay within a designated amount of time.

However, for smaller, more impulsive clients, I tend to bill more frequently.

The danger with more frequent billing cycles is that they suggest shorter-term project timelines. If you’re looking for a little extra side income, there’s nothing wrong with this.

However, If you’re looking to build an extensive and long-lasting freelance business, this is going to get very, very tiring.

3 things to remember when invoicing:

1. Focus on finding 3-5 long-term clients who you can bill to monthly.

Remember, our goal as freelancers shouldn’t be to get our hands in as much as we possibly can.

The key to freelancing is sustainability. If you find yourself focusing on one-off projects and billing daily or weekly, your drive is going to fizzle out like a match in the wind.

2. Only rely on short-term work when long-term clients are slow.

These types of one-off projects should be considered supplementary to a more reliable stream of income.

If we’re thinking “sustainability”, these short-lived projects are not ideal. Not only will you have to bill more frequently, but you’ll have to invest a lot of time and energy into populating your work queue, which is an exhausting song and dance that could fill another blog post on another day.

3. Remember your craft.

Take a systematic approach to invoicing your clients so that it feels like an extension of your craft and less like an annoying pile-up of emails or voicemails. Make sure your clients know when to expect an invoice. Bake an agreement into your contract.

The last thing you want to do is bill a client when they aren’t expecting it. This is a breeding ground for uncomfortable conversations and it will totally kill the creative vibe.

Instead, set the expectations when the project starts, and don’t deviate! Injecting some subtle branding into whichever delivery method you choose will help ensure a positive brand experience from start to finish, with little room for surprises along the way.

What methods for invoicing do you find successful? Let me know in the comments!


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  1. I try to invoice at least twice per month, but if I have a new ‘one time” project, I write a proposal and collect a deposit before beginning, and invoice to collect before or when final art is being delivered. Some months have more paperwork than others, but using quickbooks helps me have the format and process as efficiently as possible.

  2. Drew, I totally agree with your statement The key to freelancing is sustainability. From my experience the best is to have up to 5 long term clients. I usually discuss terms of payments at the beginning and once again before issuing first invoice – to confirm the payment terms and make sure my clients are aware that they are supposed to pay me in 14 days. 14 days works the best for me and it is acceptable for most of my clients.
    I use invoicing software and recurring invoices.

  3. I’m primarily an ArchViz artist who will put out an occasional logo or book cover to keep things interesting/fill gaps. Even though I have repeat clients, all of my works are one-offs. I typically send an invoice with the final files. Though a couple situations have left me considering “no files until payment is received” with new clients.

    1. Joshua, What I do for one-off projects is require half payment before starting the project, and invoicing for the balance at completion of the project. And unless it is a time-sensitive project (and aren’t they all), hold on to the final files until final payment is received. If the client stiffs you, you at least have half of the money and the files. That’s better than no money and no files. 😉

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