I've done freelancing work for a little over a year and by and large have been paid very reliably, with one notable exception. I've set up payment in stages with one of my clients, and the project is on hiatus while the client figures out what they wants next. I'm happy to put the project on hold, but I'm awaiting final payment, and I have been for several months. I've sent the client several emails. They responded to the first email with a vague promise of payment but have not responded to the next few emails, politely reminding him about the outstanding payment.

To complicate matters slightly, the client is the son of a family friend. I want to remain in good standing with him, but I also do wish to get paid in a timely fashion. I'm not sure how to push this issue without coming across as rude or abrasive. How can I confront him about the outstanding payment while remaining professional (and preferably, allowing him to save face)?


4 Answers 4


Business is business and friends are friends. Granted, you might not have won the project had it not been because of your friendship, but you should keep the two as far apart as possible.

Send an invoice in the post - forget email which is fine for regular invoicing and regular payments, but if your emails are not getting the desired response then sending more is unlikely to prove any more successful. Avoid threatening letters - Send the invoice to your direct contact, via the post, stick a post-it on it, and ask "Can we do lunch and discuss this?"

A few days later, follow it up with a phone call and ask for a meeting. Tell them you value the relationship and you don't want to rock the boat, but silence leaves you in an difficult position. Ask them if there is an issue with the last invoice. If they can't or won't pay you 100%, then seek a middle ground. 50% of something, and a luke warm relationship is better than 100% of nothing and a cold relationship. If no compromise, then you need decide if the money you are owed is worth a fight or not.

I've been in a roughly similar position in 2014 - a client that has always been both generous with work and money all of a sudden stopped paying. Their accounts department would not acknowledge any of my requests for an update. We're talking about 25% or more of my entire yearly revenue was outstanding and after seven months it got paid. I met with my direct contact more than once for lunch during those seven months - I knew he could influence progress but was not in direct control. I still consider them friends and don't know how to avoid a repeat of similar situation. It is, I suppose, part of doing business.

Best of luck!


I'm assuming the project merely is on hold and will restart once the client gathers requirements and possibly budget - and that it would cost them a substantial amount if they decide to move forward with another freelancer.

If the above is somewhat accurate, you do seem to have some leverage as you can insist on bills being paid before further work commences. Problem (usually) solved.

If not, your leverage vanishes and you will have to move into the discomfort zone. In similar situations, I have found it important to escalate every single time. Not by huge amounts - but clearly increase the pressure noticeably, increasingly using neutral rather than 'nice' language.

An email reminder is fine for starters and could be followed up by another more 'professionally worded' email, possibly cc:ed if relevant. After that, I would move on to a letter with the same level of language - and after that a final letter mentioning you will have no choice but send your claim to a debt collector of some sort.

Part of escalating is also keeping a tight but reasonable time schedule - so no more than 1-2 weeks between the notices. If the client recognizes your claim as legitimate and your communication is professional, there is no reason the client and you cannot continue doing business.


In addition, if the client company consists of several departments with very different agendas, it may work to your advantage. If you actually work for Dept A, but Dept X has a hand in whether you get paid and basically don't care what the effect is on Dept A - you might be able to get Dept A to apply pressure internally. This sort of scenario is always way better than standing alone outside the company.


"Saving face" isn't helping you at all when your bills are in the mailbox and collection agencies are calling you. What kind of so-called friend doesn't meet his or her obligations?

Try small claims court, if that's an appropriate venue.


Did you put all of these in writing? I hope you did so you can take legal actions as a next step.

Tell it formally that it's just business and nothing personal considering they are a family friend.

You may also already be doing these things but you may want to follow these guidelines for your next client:

  • Do some detective work
  • Get it in writing (contracts are always good to protect both parties)
  • Bill up front (down payments establish trust in the transaction)
  • Track your time accurately and know what you're worth
  • Use a professional invoicing software
  • Make it easy for clients to pay you
  • If conditions change, outline it in the contract.
  • Know when to stop
  • Trust your instincts

All these tips are outlined in this article: How to Make Sure You Always Get Paid as a Freelancer or Consultant

Hope those tips help!

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