Based in Chicago, Illinois, The Freelance Beat is a blog exploring the triumphs and challenges that freelance journalists encounter in their early and mid-careers.

Should You Hold on to Difficult Client Relationships?

Should You Hold on to Difficult Client Relationships?

If you freelance long enough, you’ll eventually get a client who’ll rub you the wrong way. Maybe it’s something small like a misunderstanding over an email or draft of copy. Sometimes, it’ll be more serious. Perhaps, your editor doesn’t like your writing style or doesn’t agree with the direction your story is taking.

I started thinking about this after the Chicago Reader’s recent cover art debacle ended in widespread criticism from Chicago’s black political leaders, readers and writers, including the writer whose work the artwork was supposed to complement, Adeshina Emmanuel. In a piece he penned for the Columbia Journalism Review, Emmanuel detailed the full story behind the controversial cover, which depicted wealthy gubernatorial candidate J.B. Pritzker talking on the phone and sitting on top of black lawn jockey’s shoulders while an FBI agent listens to his phone call. The artwork, many felt, not only played upon a racist trope but also distracted from the piece it accompanied. If you missed the piece in my newsletter last week, you can read it at CJR.

What struck me most about Emmanuel’s story is the behind the scenes negotiating that took place. It’s natural for editors and writers to have a back and forth over word choice or a better kicker quote. But when interactions between you and your client escalate beyond that, it could lead to a lot of stress between you and your client.

This is particularly problematic, because you need clients in order to put a roof over your head. And as more workers transition into freelancing, I’m worried about the lack of protections for freelance workers. If you’re self-employed, where’s the safety net if you lose a client? What if you need help affording health insurance? What if you feel discriminated against based on a client’s behavior? I’m no labor law expert, but these are some of the things we need to think about as more workers shift toward freelance work.

Thankfully, most people are good people. But despite being mostly lucky in my industry, I’ve also had a few bad experiences, each of which has taught me valuable life lessons. If you’re stuck in a tough client or work situation, here are some questions you need to ask yourself to assess the situation:

Can you address the problem head on?

Talk with your client directly about what’s going on. Try to be as clear and fair about the situation. Explain why your grievance in a concise, professional manner and give your client a chance to respond and process the issue(s).

What’s the best way to solve this problem?

One of the most valuable pieces of advice one of my professors gave me was, “Don’t come to the table with problems, come with solutions.” Think about possible solutions to the problem and present constructive feedback. See if your client is open to doing things a new way. If not...

What are the long-term implications of this relationship?

Picture yourself retelling this story to a friend or freelance colleague a couple years from now. If you had to explain a client falling-out to a friend, or maybe even a potential employer, would you feel proud of the way you handled things? Journalism, like every other industry, is a small world. Everyone knows everyone. But in this industry, it’s even more important to maintain your integrity. For example, if you had to leave a client relationship behind because you witnessed unethical, racially insensitive, or sexist behavior, at least your conscience is clear. However, if you burned a bridge over a solvable issue, your reputation could be damaged if word got out to other potential clients.

Is this relationship worth keeping?

If a client is particularly stressful, it may not be worth keeping. If you and your client are able to find a mutually beneficial solution to your problems, whether it’s communication, edits, etc., the relationship might be salvageable. Hopefully, it’ll improve if you’ve talked about your issues. If not, the beauty of freelancing is that you can move on. Of course, much like a full-time job, your clients are responsible for your steady income. And that makes it hard for you to walk away from toxic relationships. I, a black girl from a low-income single-parent household in Detroit, have felt especially financially vulnerable to jobs or client who weren’t good for me. But I can say that you can’t do your best work if you’re not happy. And life is too short to work for clients who don’t value your expertise and work ethic.

How have handle tough client relationships? Tell me in the comments or email me at

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