Hi Captain,

Earlier this year, I agreed to do some work for someone. We hashed out that I’d do about X hours/week, and they’d pay me $Y/hour. It was a hobby that I never expected to monetize, so I was really surprised that someone was willing to pay for it. Between my two official jobs and all the other stuff I’ve had going on this year (moving, cutting ties with my abusive parents, my mental health taking a nosedive), I hadn’t even noticed that they didn’t pay me… for months, now that I look back on my records. Add to this that the work, which used to be fun, now feels like an utter chore, and I really don’t want to do this anymore.

I need a script (email or text) to deal with them. Ideally, I’d like to a) maximize my odds of getting paid (I know there’s no guarantee, since we never signed a contract or anything, and luckily I can survive without the money), and b) make it clear that I will no longer be working with them, since this behavior is unacceptable. Any advice? All my attempts at writing something come out rude and profanity-laden.

-Why Does Everyone Feel Entitled to Free Millennial Labor?

(He/him.)

PS – any advice on not feeling foolish and irresponsible for not noticing this sooner?

Dear Free Labor,

My instinct says that the “please pay me now” and the “I’m quitting” conversation are two separate conversations and you should start with getting paid.

My first question is, have you invoiced the person for the work?

If you haven’t invoiced them, stop everything and make an invoice. Put a clear “payment due” date on it – I’d say 10 days from when you send it – and write an email like this:

Dear (Friend): My invoice for (dates) is attached. The best way to pay me is _______ (I’d choose an app or electronic method so the funds drop immediately), and payment is due by ______. Sorry to let these pile up, happy holidays!

If you have invoiced them, dig out all the unpaid invoices, make an invoice for the current month, and attach them all to a new email:

Dear (Friend): Here is my latest invoice, as well as the past due invoices, totaling $$$$. Please pay me via ________. Payment is due by ______. Thanks and happy holidays!

No explaining why you need the money. NO FEELINGS or apologies or justifications, especially in the second note. You are owed this money, you are not making it weird by asking for it in a quick businesslike way. You are actually doing them a favor by making it explicit, since somehow they never managed to say “Hey, how much do I owe you?” or “How do you like to be paid?” or “Send me your invoice so I can settle up with you,” this whole time. A good-but-absent-minded person is going to be relieved to have this settled.

Hopefully one of those emails will solve it – the person will say, “OMG, of course, here you go” and the money will hit your account soon thereafter. The only right thing for this person to do is to pay you, without argument or hassle, as soon as humanly possible. If they don’t, here’s the trick:

Don’t do or schedule or talk about any more work for this person until you’re paid. If they try to schedule you for something, say, “I can’t really commit to any scheduling right now. Let’s talk about it after payment has come in.“

If you’re holding on to work product, don’t turn it over until you’re paid. “I’ll be happy to send the files over as soon as the payment shows up!“

On the due date you specified, if payment hasn’t shown up yet, call your friend on the phone and ask where the money is. “Hey Friend, payment hasn’t shown up yet, when should I expect it?” It will be seriously awkward, but you’re not the one making it so.

The “I’m quitting” conversation is for after you’ve been paid, and the end of the year/beginning of the new year is the perfect time to discuss it. The reason I say that is, if the person still wants you to do more work for them, they might be more apt to pay in order to keep the relationship sweet. If they feel like a bridge is being burned anyway, paying you might go further down the priority list than it already is.

Once you’re paid, your script for quitting might go like this:

“Looking at my commitments for 2017, I’m not going to be able to continue this project. Thanks for the opportunity, it’s been a pleasure.”

Polite, professional, friendly, over and out.

If they don’t pay, hassle you about paying, try to make it sound like it’s your fault you haven’t been paid yet, try to renegotiate what they agreed to, they are taking your relationship with them and setting it on fire. In that case, it’s okay to skip to “Eff you, pay me” or bring in an outside service or even a collection agency. The amount of money at stake here might not make those steps worth it right now, but know that you are in the right and you’ve got options.

As for feeling foolish, forgive yourself – you had A LOT going on this year! You’ll never make this same mistake again, and there are valuable lessons to be gained:

Spell things out in advance in writing, even when working with friends. Especially when working with friends. “I’m excited to work with you – let’s spell everything out in writing so we know exactly how this is going to work.” Good contracts protect everybody. Don’t work with people who think they are unnecessary.

Be explicit and clear about payment schedule and expectations. A lot of freelancers I know put a penalty for late payment into their freelancing contracts for just this reason.

Whenever possible, tie deliverables explicitly to payment.”Payment due immediately upon delivery.“

Keep up with your invoicing and record-keeping. Less chance of unpaid bills piling up and you’ll be happier come tax time if you do.

Lose the shyness or awkwardness about asking for pay and expecting to be paid. Lots of people feel awkward talking about money, but if you can practice and learn to not be awkward, you’re doing yourself and everyone you work with a favor by bringing it all out into the open.

Good luck getting paid! You got this!