Where’s my money? Navigating the emotional tax of chasing freelance payments

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There are lots of reasons to go freelance. 

You get to “be your own boss” and carve your own path in the world. Take days off whenever you feel like it and cherrypick your clients as and when it suits you. And you don’t have to answer to anyone (other than the tax man, of course).

Don’t get me wrong, I would never go back to working under somebody else’s thumb. However, there are two major drawbacks to the freelance lifestyle that understandably turn off a lot of potential freelance go-getters: The lack of paid time off and chasing up payments.

As far as the former is concerned, there’s not really anything we can do about that. It sucks and it’s a substantial pill you’re just going to have to swallow. But the latter is something we can actually do something about.

So, why then, after 15 years as a freelance writer, do I still spend at least a few tedious and humiliating hours a month chasing up late payments?

The endless grind


There comes a point, typically towards the end of each month, where I fall into the semi-conscious routine of opening my online banking app every few hours just in case that big invoice I’m relying on to pay the mortgage has come through.

Of course, the rational part of my brain reasons I should simply pick up the phone. But the anxiety-ridden lizard brain always wins that toss-up and instead I return like clockwork to the ceaseless tapping and waiting routine.

I am, after all, a creative above all else and creatives, generally speaking, are a notoriously neurotic bunch. For somebody working in finance or something equally horrible, it would probably take them seconds to sort the problem with a quick call and a gentle reassuring chuckle

But I’ve led myself to believe the phone call is the nuclear option and even the “nagging” emails often give me a subtle pang of shame. It’s an endless grind and it’s both financially and emotionally draining. It’s also not something I’m particularly good at, so you might assume I’m not exactly best-placed to offer advice. 

This is why I’m essentially writing this article to and for myself. If I can inspire others like me to actually take the reins and do something about their perpetual hells then all the better.

Taking control of your late invoices

After reading several similar pieces on the subject and examining my own recent history, I’ve settled on 5 things that all freelancers (myself included) could and should be doing to escape the emotional tax of freelancing.


1. Sign a contract

I know it can be incredibly awkward to put together a contract and word it in a way that doesn’t make you sound like a pompous oaf but it’s something you’ll only ever have to do once. And don’t feel bad about demanding a signature either. You are a professional and you are being hired to do a job that you’re bloody good at. When working for friends, you might assume a contract would create a rift. But, if anything, it’s more likely to be used to stop an argument in its tracks. So yes, even when working for your mates, get it in writing. 

2. Check your terms

Anyone who has ever filed an invoice should know that it’s common practice to give a client 30 days to pay. That doesn’t mean they should be aiming to pay at the stroke of midnight on the 30th day, of course, but it does give them a solid month to sort the finances out on their end. If they can’t pay you after 30 days, that’s when the trouble starts brewing. Of course, that trouble is a lot less likely to reach boiling point if you have a late fee stipulated as part of your contract but building a late fee into the deal from the start might, unfortunately, put some clients off. 

3. Send your reminders ASAP

Don’t wait around until it becomes something easy to ignore. If the 30th day ticks by and that invoice still hasn’t been cleared then send the first shot across the bow (by which I obviously mean email). It should be a calm, collected and thoughtful email that you can comfortably copy and paste (no need to waste any more of your precious time, right). It might also be all it takes. But then again. It might not be.

4. Contact the right people

Now, this depends on the size of the organisation you’re dealing with but, in my experience, if you’re trying to get a larger client to pay up then you really need to be talking directly to the finance department. Quite often, the editor you’ve been emailing back and forth with for weeks will turn out to have next to no idea how payments work. And, quite frankly, why should they? So ensure you’re emailing the people who actually control the cash.

5. Be flexible

Don’t be flexible with how much you charge. You should know how much you’re worth by now. But by all means, be flexible with how you get paid. If a client, for example, says they can pay you right there and then if you accept payment via PayPal then you might want to consider swallowing that transaction fee, particularly if you’ve been holding out for that particular payment for a while

What if that doesn’t work?


Honestly, no matter how careful you think you are, if you work as a freelancer then somebody at some point is going to take advantage of you. But that doesn’t mean you should burn all bridges at the merest sight of potential trouble. Be polite and direct and make yourself a boil on their arse if you really need to but don’t get angry and don’t threaten legal action until every possible alternative path has been exhausted.

And if all else fails, maybe try picking up the phone?

Header image by Manuela Fiori


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