My biggest client referred his best friend to me. That friend stiffed me on my invoice. What can I do without ruining the 15+ year relationship I have with my client?

In a nutshell, my best and biggest client referred me to his close friend for some IT work. It came as an emergency. I did my best, and I got my client’s friend up and running again.

Over two visits, the friend accumulated $1600 worth of time within a few days. Both of his checks bounced. His business went bankrupt, and he claimed creditors to be relieved from, but I wasn’t one of them. I got his word he would pay me and that he appreciated the work I did for him.

Time went by. Nothing happened. I asked my client about his situation and from what I saw, my client was also one of the people his friend borrowed from. I’m unsure if he was someone he was relieved from.
When I asked my client if I should pursue it, he said I should drop it that I would probably never get the money back.

That $1600 isn’t chump change. With the economy like it is, I could sure use it. I don’t want to alienate my client, but it burns my ass that his friend got off, especially since he’s rich and lives in an exclusive neighborhood, nice cars, has another business which is flourishing, etc.

Signed,
A freelancer with a burnt butt

Additional context: the freelancer who wrote in has been in IT since 1994, and he started his business in 2004. There are no contracts involved in most of his work, as most of his clients have long and personal relationships with him – often spanning over a decade.

Honestly, it seems like you've already reached the conclusion on this: it's frustrating, but that money is likely gone. A lot of time has passed, and there was no contract in place. It's certainly possible there's a route you can take to regain that lost $1,600, but I don't see a way that's worth that amount of money – almost all of them will cost you in much more damaging ways.

I respect the crap out of the style of work you offer – close relationships, time-honed offerings, constant support – but it's a style where a contract-free experience should only be offered to proven and qualified clients. As you stated (this was in a separate email), it's the newer clients that take advantage of your stalwart offering.

I'd suggest taking a look at how you qualify these new clients and if there's a way to offer an expedited contract or down payment.

Here's how I deal with this: I have a simply-worded and short contract template that I use for clients I'm unsure about. I fill in the blanks with the client, and that ensures we're both on the same page regarding it (e.g. what results do they expect? what services do they need? who's my main contact? who's in charge of payment?).

My first meeting or two with the client is spent gaining an understanding of their issue, offering my solution, and engaging them for the work. My third meeting is a 5-45-minute engagement where we fill in those contract blanks and ensure we understand each other. I'm protected, my client is protected, and we’re both clear what I'll be doing with them. Plus, that contract-creating experience is my built-in client-qualification system.

I also suggest you check out the Freelance Isn’t Free act. I think you’ll be interested in supporting it.

Otherwise, I wish you the best with your future clients. I know a principled business (with such a remarkable pedigree) will do just fine in the long run, so my final piece of advice is this: don't sweat the crappy experiences. They seem to be few and far in-between.

Bryce Bladon runs Clients From Hell, hosts a popular podcast of the same name, and runs a monthly webinar specifically for freelancer FAQs.

Follow him on Twitter.
Or don’t. You do you.