How to deal when a client relationship falls apart

If you're in the business longer than a few months, it will happen

Hi friend,

Photo by Karin Hiselius on Unsplash

I was sitting at my desk when it happened: I got the dreaded email that every freelancer hates. The one that would ultimately terminate my relationship with a client.

“Hey Heidi, It’s not working out. You’re not giving us the content we need and it’s not worth our time to try to walk you through it. Can we talk about getting some of our deposit back?”

It felt like a gut punch, I assume. I’ve never actually been punched in the gut. I have had a horse step on my foot and crack the bone, so maybe it was like a gut punch to my footbone (don’t ask me which bone, I’m a writer, not a footbone expert).

I had done everything I could to stop the project from going sideways - asking for clarification, begging for feedback, consulting a magic 8-ball for guidance - but despite my best efforts, I was staring down the barrel of a client breakup email. And although it wasn’t the rudest email in the history of the world, it wasn’t particularly nice.

“It’s not worth our time?” What does that even mean?

So for about 60 minutes, I indulged in extreme self-pity. If my life were done in a reenacted in a biopic, this would be the moment where Sandra Bullock stares out a rain-soaked window crying while drinking a large mug of wine and wrapping herself in the comfort of a cozy sweater.

I told myself every freelancer’s favourite go-to mantra, “You’re a terrible writer. You’re lousy with clients. Everyone is going to know it now and see that you’re an imposter.”

Until I gave the relationship breakdown a bit more thought and realized that, while there were certainly lessons to be learned, they weren’t necessarily in the “be a better writer” category.

Lesson 1: Listen to my gut

Whether you call it your gut, your intuition, or your footbone, listening to your instincts is an important skill that should be honed. In almost all of us, our gut is infinitely smarter than we give it credit for. Often, when we say we don’t trust our gut because it’s led us astray, what we mean is that we overruled it when it tried to warn us and are now blaming it for not kicking in more aggressively.

How do you hone your instincts? By paying attention to when listening to your gut worked out and when ignoring your gut didn’t work out. But be honest that you dismissed your gut instincts.

In this case, from the very first meeting, my instincts told me this wasn’t a great job for me. The client (a lawyer) came across as a micromanager. He complained about the previous freelancers he’d worked with. He wasn’t overly interested in answering my questions.

It would be one thing if there had only been one or two red flags that the project wasn’t a good fit. But from the get-go, I was conflicted about taking it on. Nothing about it felt right.

I didn’t listen to my gut because this was during Covid and money was tight. So I told myself I was just being paranoid. I told my gut to knock it off and I ignored it in much the same way I ignore calls from unknown numbers. (Which I literally just did as I wrote this paragraph. Sometimes life and art do collide.)

Lesson: When my intuition screams at me (like the best friend in a horror movie) not to take on a project, I need to listen more closely and carefully.

Lesson 2: Don’t take on work I don’t like

Just because I love writing doesn’t mean I love all writing. There’s writing I’m not great at and there’s also writing I don’t love (just like you can love some types of ice cream but then absolutely hate Rocky Road, which is objectively the worst of the ice cream flavours).

I hate doing website content, especially for law firms. The writing is dry, most law firms just copy what everyone else is saying, and (between you, me, and the walls) because lawyers tend to write a lot in their work, they also tend to think they understand content, especially content for their website.

I had told myself repeatedly before this project came along that I wouldn’t do any more website copy. And yet still I’ve taken it on sometimes.

Here’s the thing, every single time I’ve taken it on, I’ve regretted it. Some people love doing it, and I say that’s outstanding for them. I’m happy to send that work their way. Because it is not what I enjoy, and short of a million dollars, there’s almost no amount of money that would make such a project worthwhile for me.

Lesson: Stop taking on writing content for websites (or, stop taking on work I already know I hate).

Lesson 3: Let dread (or relief) be my guide

It felt terrible to be broken up with, but I knew the situation required more reflection when I realized something important - despite how terrible it felt, I was relieved the client was gone.

For weeks I dreaded opening emails from this client because even in the somewhat positive emails there were still comments that rubbed me the wrong way. I delayed sending him the second round of revisions because he had torn apart the first round without offering constructive guidance and I deeply wanted to make everything perfect. I spent more time fretting and fussing about it than a beauty pageant mom does over her six-year-old’s hair.

The time and effort I put into it far exceeded what I was being paid. By the end, I dreaded going to my computer because I would have given anything to avoid that project. It was tainting my other work.

Now that I’m older and (theoretically) wiser I likely would have walked away at that first meeting. But if I were to do it again, I think I would have realized part-way through the project that the dread I felt at working on it, combined with how I felt after his response to the first draft of his website, was a sign that we weren’t a good fit. And I could have ended the relationship on my terms, rather than him ending it on his.

Lesson: If I’m relieved to be free of the client, it’s not worth wasting time or energy second-guessing what the end of the relationship says about me, my skills, or my worth as a person.

Lesson 4: Where possible, don’t make decisions solely based on money

I know this is a tough one, which is why I added the “where possible.”

Sometimes, you have to do what you have to do. However, most of my worst decisions have been because I felt desperate to make money. When you’re desperate for money, you take on projects you otherwise wouldn’t, despite red flags going off like grenades in a war movie.

You overrule your best instincts and justify doing work you wouldn’t otherwise do. You’re also far more likely to take on such projects at a much lower rate than you deserve, which might get you money in the bank in the first place, but in the end, is often counter-productive.

Lesson: If money is the sole reason for taking on a project, it’s probably going to be more trouble than it’s worth. Be prepared for things to go south, quickly and dramatically. (Related: my post on the most important tool to give yourself power in client relationships.)

Lesson 5: Ask yourself some questions

Even given all the above, it’s still important to take a lesson away from this situation. Because the power is in acknowledging where we can change how we operate moving forward.

So there are four important questions you can ask yourself after a client relationship implodes. These help you determine how responsible you should feel for things falling apart. This week, I’m doing my Insider Insights as the final section of this post, rather than as a separate post.

(A reminder that next week is our co-working session. If you’re interested in joining us, just like or respond to the post and I’ll send you a link a few days before. For February, we’re focused on doing tasks that make us uncomfortable, although you can join us and work through any task you like. Here’s more information.)

Insider Insights

When a client relationship goes south, here are the four questions to ask yourself: