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I have had a client for about a year, and I did a bunch of work before billing them - they were totally fine with the bill and everything and it wasn't anything too crazy (a couple of thousands of dollars over the course of about 6-8 months of intermittent work). I was a new freelancer and afraid of billing at that point (I've gotten over my fear by now).

Anyway, we agreed to a payment plan of $500/month, due on the first of each month.

I haven't done any work for them this month (not totally crazy, not every month has a lot of work for this client), though there might be a couple of minor items in the backlog that neither I nor the client has prioritized. I also haven't been in communication with them since last payment.

When and how should I gently remind them that payment is due? I've been doing business with them for a year and they've always been good about payment, so I don't want to be TOO much of a stickler for payment on the exact day it is due, especially during a week with a holiday, but I also don't want this to languish too long, especially as they've got several more payments before they are paid off.

Should I maybe ask them if anything needs to be done/mention minor backlog items? Or should I just bring up payment? The latter seems a bit harsh.

How long should I wait after the 1st to bring it up? It's the 3rd now, so not too crazy still, but I feel they either forgot, or "forgot".

closed as off-topic by gnat, Peter M, scaaahu, OldPadawan, HorusKol Jul 4 '18 at 11:02

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    What does your contract say about late payments? Have you been sending them regular invoices each month? – taffy Jul 3 '18 at 17:37
  • This was an early client, so I have no contract besides messages between him and I (where he does explicitly state in writing that he'll pay the first of every month). Nothing about late payments and I haven't sent an invoice this month so far. – Joe Smentz Jul 3 '18 at 17:38
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    I'm voting to close this question as off-topic because it belongs on freelancing.stackexchange.com – Peter M Jul 3 '18 at 18:57
  • How do they pay you - mail you a check, electronic payment, or give you a check/cash when you're at their office? If it's mail, there's nothing wrong with calling to check when they sent it (once it's been long enough that a payment sent on the 2nd (first business day of July 2018) should have arrived).E-payment, Contact them to make sure they've go the right account info; in-person, call them and let them know it's OK to mail the check this time, or offer to come down and pick it up. If possible, give them an out so they don't have to admit fault. – RDFozz Jul 3 '18 at 23:23
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Some payments have a 10 day leniency on them from their due dates, that seems like a good number...

Asking for payment isn't rude as long as you ask in a civilized manner, however I bet they're going to say something like they don't need to pay you because you haven't done anything for them, so be ready for that.

  • I mean, they've never expressed that beforehand. He seems to understand that he owes me for past services rendered and has been paying me back over time. – Joe Smentz Jul 3 '18 at 17:39
  • @David Maybe they just forgot about you :) – RandomUs1r Jul 3 '18 at 18:38
  • This seems like a good strategy to me. The client paid a few days after it was due. – Joe Smentz Jul 6 '18 at 14:33
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The customer requires a lot of responsibility from you. They expect you to work hard, deliver, and respond to them in a timely manner. It's hard work.

In turn, the customer has ONE responsibility to you: they have to pay their bills. On time, in full. If they aren't paying you, then they aren't your customer!

You need to be proactive and insistent. Train your customer to pay the bills on time, in full. If it goes just one day late, stop work. Fix the problem. Bring it up, don't be shy. Get the money.

Tony Soprano had a great quote, I'm paraphrasing, but it was something like: "Teach them that they need to pay because they have to, not because they're doing you a favor."

  • That's a good mindset. And one that has been difficult for me to get into. I have historically had a lot of imposter syndrome, though I've gotten it more and more under control as I've realized that someone capable of delivering what I can (full stack web, mobile apps and also sys admin stuff) is pretty rare or at least in high demand – Joe Smentz Jul 3 '18 at 18:14
  • We've all been there. I had to learn the hard way about collections. It's a mindset thing, like you said. I send out a friendly reminder the day it goes past due and work stops in the meantime. Second notice is perfunctory. Third notice is demanding. Collections hasn't been a problem in years, but it was non-stop at the beginning because I didn't want to be a bother. So yeah, mindset issue. – Rocky Jul 3 '18 at 18:19

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