Bullish Q&A: Terrible Clients and Their Terrible Behavior

Buildingwork for the future

I have this great freelance client – but his girlfriend is another story. She doesn’t work for his firm, but she likes to give lots of unsolicited advice that actually isn’t good advice. She recently messaged me a really rambling complaint, late at night, about how I’m doing things with my client’s business, and instead of getting into it with her, I opted not to respond because her message was so combative and inappropriate. However, my client called me yesterday and basically begged me to “work with her” for the sake of their romantic relationship.

My client is a great guy but I’m not sure if I want to have to answer to his girlfriend too. I sensed trouble from the start with her – jealousy, weird competitiveness, etc.

How would you navigate this weird situation? I cheerfully told my client, “I wasn’t even aware there was a problem between me and your girlfriend! Of course I’ll work with her!” But now I kind of feel like if his lady friend thinks she can do my job better, it’s better to just walk away and let her instead of dealing with weird late night messages and extreme passive aggression.


Oh yikes! That sounds terrible. Once, my web design company outsourced some of our backend development work to another company owned by a husband and wife. I communicated only with the husband, and we got along great. Then one day he forwarded one of my emails to some other people on the team about a joint project (all normal). His wife somehow managed to add my email back onto the recipients list when she replied, “I really don’t like her or her tone.”

Obviously, it was never quite the same.

On the other hand, plenty of people don’t like me or my tone. But plenty of people do, and I’m at a stage in my career where I can talk almost entirely to those people.

So how bad do you need this client?

It sounds like he knows his girlfriend’s advice is unreasonable. Some options:

  • You could tell him you insist that all clients provide a single point of contact for you. If he were a ten-person company, you’d still want to talk to only one person.
  • You could develop a web form and insist that all clients put requests into the web form. Set up an autoreply so if she emails you, it bounces back with a link to the web form. Obviously, this will enrage her! Will it make her back off? Will it break them up? Will your client wrest back control of his professional life? Soap opera fans want to know!
  • You could invite them both out to lunch, and look really ugly at the lunch. I’m sort of joking, but maybe not? Bring a fourth party to defuse the situation and more profoundly outnumber her.
  • You could regretfully tell your client that working with him isn’t a good match anymore. He’ll know why. Maybe he will beg to get you back, and solve the problem on his end.

Or, alternate theory: Is there a chance she’s the sane one, and he’s totally wasting his money on a fruitless business that’s bankrupting their future together? Just throwing that out there. Like when Liz Lemon’s boyfriend Criss started a terrifying hot dog truck that looked like he was maybe trying to kidnap children?


Also, I don’t know what service you’re providing or how you bill for it, but I can tell you how I solved one similar situation. I was working for a startup run by two co-founders who had weird late-night ideas they would ask me to execute. They did not run these ideas by each other first, and oftentimes the ideas were both silly and mutually exclusive. (Put a link to every piece of content on the site in an alphabetized list of links, above the site nav? Change the homepage to a giant picture of a birthday cake?)

I spent a lot of time writing back and trying to argue them out of their ideas (or at least try to get them to pick one idea), which just made them mad. Eventually, one of them said something to me about how I wasn’t really part of the company (no shit), so I shouldn’t try to make their decisions. Lightbulb moment: “So, you would like me to execute every request that comes in from your company without question, in the order they are received?”

That was indeed what they wanted! So I would put a link to every piece of content on the site in an alphabetized list of links above the site nav at 1am, and then wake up at 9am, see a new email, and change the homepage to a picture of a birthday cake. And then at 10am, upon receiving an email from the first guy, change it back to the list of links. It was meaningless and ridiculous, but I guess it made the clients feel powerful, and it certainly racked up hours on my invoices! Everyone was happy.

In the future, you might want to set some ground rules for new clients – especially the “single point of contact.”

And never get complacent – even if you’re fully booked, keep hustling for new clients! That way you can fire the bad ones (and raise your rates). This is a constant cycle – out with the old, in with the more profitable and enjoyable to work with.

GetBullish 20 Day Money Reset Journal resting against a sandy background


Our Latest Products