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I love freelancing. I really do. As long as the work is coming in and I’m the master of my schedule, what’s not to love? There are a lot of benefits to being an independent worker, but the one part I hate – and I mean deep, seething hate with the intensity of a thousand exploding suns – is chasing my money.

There’s no rhyme or reason to it – big clients, small clients, agencies, partners I’ve worked with for years – eventually, someone doesn’t pay a bill on time – or AT ALL. And as the renowned Big Perm* once opined: “Playin’ with my money is like playin’ with my emotions.”

You see, steady income is NOT one of the benefits of freelancing, unless you happen to find the unicorn sitting on the pot of gold at the end of a rainbow with a solved Rubik’s Cube that we like to call “retainer work.” So when invoices aren’t paid, it very directly impacts my day-to-day life. Which leads to stress. And stress is not why I got into this.

Another part of the stress is the uncomfortable conversations that have to happen next – because even though we have a contract and a scope of work in place, I still feel like a hobo with hat in-hand, asking if they can spare a dime. It’s my money, you owe it to me, but somehow, I feel bad asking for it. Well, not “bad,” but like I said, UNCOMFORTABLE.

“Remember when you asked me to write your brochure and I said I would and then I did and then I sent you an invoice 60 days ago? Yeah. When are you going to pay that?”

I’m not an accountant. I’m not a collections specialist. I’m a copywriter. My introversion is at a stage where I don’t even like talking on the phone to people I LIKE. So, calling people and basically saying “where the hell is my money??” is not fun. At all. Especially when I have to do it more than once with the same client, because it definitely factors into my decision the next time they show up with a new project.

This means I can potentially lose a client, which once again impacts my income. But if they’re not paying anyway, it’s not really income anymore, is it?

But.

In my almost decade-long freelance journey, here’s what I’ve learned when it comes to making sure you don’t have to hire a “Big Vinnie” to visit your clients:

Get to know their accounting department.

No matter how high up your contact is, Accounts Payable cuts the check, and always will if you have a valid contract. No runarounds, no BS. Get to know them. Send them cookies. And have their direct number.

Spell out all terms in the contract.

This isn’t 1940, and a handshake ain’t cutting it. You want payment 10 days after invoicing, PUT IT IN THE CONTRACT. Once they sign it, it’s binding – and makes things a lot easier when you have to have those conversations.

Give a grace period.

Don’t bother calling on the 31st day if you’re net 30. You’ll get the “it’s going out today” line (and it’s not going out today). So, give your client a full week after the due date to account for approvals, mailing, etc. You won’t stress, and they won’t think you’re psycho.

Have a cushion.

If you’ve got an accountant of your own, you should already know this. When things are going well, set aside a cash cushion for when things are slow (or payments are late).

Only go the lawyer route as a last resort.

You pull out the attorney card, and you may finally get paid, but you lose a client. And you have to pay a lawyer. Which is, once again, less money. So make sure you’ve explored every avenue possible before pulling the trigger on this one.

Thankfully, I’ve (knock on wood) never been completely stiffed by a client, and with some patience and common sense, you won’t either. And I’m pretty sure Big Perm will be my next Halloween costume.

*I still can’t get over the fact that “Friday” came out 20 years ago. But it’s still a damn good movie.

Kwame DeRoché is a Brooklyn boy living and working as a copywriter and creative director in Washington, DC. If you don’t like Sci-Fi, pizza, or the Yankees, expect a lot of side eye.