What your invoicing habits say about you as a freelancer

I’ve been running my own business long enough to know that absolutely no one gets into business because they love invoicing.

And since it can be such a pain, it’s easy for us to overlook invoicing or pay very little attention to it.

But have you ever stopped to think what your billing & invoicing habits say about you as a freelancer? What do your clients (or future clients) think about you based on:

  • How and when you send invoices?
  • How you respond to late payments?
  • How you react to prompt payments?
  • Whether you bill upfront, along the way, or after completion?

Each will shape your relationship with your clients and could impact your brand or even your potential for revenue.

What your billing habits say about you as a freelancer

In today’s post, I’d like to explore a few things your billing habits say about you as a freelancer.

screen-shot-2016-10-19-at-4-20-42-pmThis article is sponsored by AND CO. With a sleek app and a real-life human on your side, AND CO is all you need to take the headache out of billing as a freelancer. Sponsorship has not affected the value or content of this article. Learn more at and.co

If you never follow up on late payments

What this might say about you: Getting paid isn’t actually that important to you.

You aren’t very organized in the things that matter most because, if you were, you surely would realize you have an unpaid invoice and follow up on it.

Or maybe you do know about it and you’re too afraid to approach a client directly. Which shows a lack of maturity as a business-owner.

Believe it or not, businesses who have to pay invoices months after they’re due because you never followed up are less likely to work with you again in the future.

It creates extra work for them and puts a bad spin on your image.

If you require a down-payment

What this might say about you: You’re committed, reliable, and trustworthy.

First, asking for a down-payment before you’ve done any kind of work for a client shows that you’re committed to their project.

You’ve accepted payment for almost zero work, so now you’re indebted to your client. You pay that debt by completing a well-done project.

Having the nerve to ask for a down-payment means you better be someone a client can trust with their money.

If you request payment in full from the start

What this might say about you: You don’t trust your clients.

It’s a pretty bold move to ask for 100% payment before you’ve done any work on a client’s project.

In some cases, this might be seen as high-end or exclusive to some clients. But for most clients, this says that you’re not a trusting person. You don’t believe they’ll pay their invoices.

And when they feel like you don’t trust them, it’s almost impossible for them to trust you.

If you wait to bill until the project is completed

What this might say about you: If you wait to bill anything until the project is completely finished, you might be telling your client you’re going to overcharge them for the project.

From a client’s point of view, you might bill them for unforeseen “extras”—which means they’ll end up with a bill much higher than they expected.

Even it it’s not true, it’s a message you might be sending.

If you forget to send an invoice

What this might say about you: You don’t care when you get paid.

Taking way too long to send invoices after you said you would gives the impression that you don’t care when you get paid. This could encourage clients to take their sweet time in getting you what you’ve earned.

Also, be courteous: you shouldn’t put off sending an invoice and then demand they pay it immediately.

If you follow up too much on an invoice

What this might say about you: You look desperate.

Following up too much on one invoice might seem like you’re desperate. Yes, you should follow up as often as feels right, but make sure you never come across as desperate to your clients.

It gives them all the power.

If they get the idea that you need them in order to survive, they’ll be much less likely to agree to price increases or other improvements in the future.

The key is to make sure your client always needs you as much or more than you need them.

Everything is marketing

A commonplace piece of business advice is to remember that “everything is marketing.”

Everything you do, every way you interact with your clients contributes to your brand and image. Even invoicing or billing can send subtle important messages that either help or hurt you as a freelancer.

Need some extra help with invoicing?

If you want help managing your invoices, I highly recommend you look into AND CO, the sponsor of this article. AND CO assigns a real human being to your account who invoices your clients, follows up when appropriate, and reminds you to send invoices at the right time. They can even set up recurring invoicing. More details at and.co.


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About Preston D Lee

Preston is an entrepreneur, writer, podcaster, and the founder of this blog. You can contact him via twitter at @prestondlee.


  1. Excellent advice, Preston!
    Many professional, especially creatives, should read this post!

    The most common bad habit among freelancers is they don’t require a down-payment, afraid that the client will go away.

    But they’re so wrong!
    The client who refuses to pay us to start working is definitely the one we should avoid!
    I’ve heard so many stories of colleagues who weren’t paid at all for their work, just because clients changed their mind about a project or run out of cash!

    You are so right about the messages we give with our billing habits and I will absolutely agree that “everything is marketing”.

  2. SADHAN GHOSH says:

    Very useful tips. It exactly reflects the way it is described.

    One can meticulously follow the said invoicing and payment follow up cycle.

  3. Great article. Thanks a lot for sharing.
    I’m using MoneyPenny as my accounting tool alongside PayPal to send estimates and invoices to my clients. Both work very well for me, especially MoneyPenny as it keeps me up-to-date when my invoices for projects, etc are due or if a client hasn’t paid my bills yet.
    It also allows me to track my projects and staff’s time easily and live.


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