Writing Jobs From Hell Contest: Share Your Worst Client Horror Stories

Evan Jensen

Writing Jobs From Hell Contest. Makealivingwriting.comEver had one of those writing jobs that made you want to vomit, smash something with a hammer, or scream profanities into a pillow?

It happens. Just about every freelance writer has at least one horror story to tell about terrible clients, deranged editors, ever-changing demands, slave-labor wages, or maybe even no payment at all.

What’s one of your worst writing jobs?

If your blood pressure is on the rise just thinking about it, hopefully you learned a thing or two from the experience. You know what I mean: Fool me once, shame on you. Fool me twice, shame on me.

If you do your part to find great clients, you’re a lot less likely to work with the kind of crazy-making clients that give you nightmares months after you severed ties and swore off working for them ever again.

But before you cut up that worst-writing-job assignment into tiny little pieces, douse it in gasoline, and laugh maniacally as it burns to ashes, we want to hear about it.

Share your worst client horror story for a chance to win. Here’s what you need to know about the “writing jobs from hell” contest:

Remember one of your worst writing jobs?

Every freelancer has a worst writing jobs story. If you don’t, you’re either not working very hard, you’re brand new to freelancing, or your day of reckoning is imminent. Need something to jog your memory?

  • Maybe you’re on the crazy-train right now with an impossible client, wondering how and when you’re going to escape.
  • Maybe you’re so sick of the excuses about getting paid, you’re about ready to show up in person, bust through the doors, and demand payment.
  • Or maybe everything started out great, and now the whole project is unraveling. And it’s eating up valuable time you could spend on marketing or writing for better clients.

My worst writing job: I’ve had a few crappy gigs over the years. But the one that still gets me fired up was for a trade magazine for the tow truck industry. Not my niche. But when the editor reached out for help to salvage a poorly-written cover story by another writer, I figured I’d use my journalism chops for an easy $500.

Basically, I had to start from scratch with interviews, research, writing and rewriting. I turned the assignment in on time and waited a reasonable amount of time for payment. Then excuses started rolling in. Then they stopped returning my emails. Then the site went down and the trade pub folded, and that five hundred bucks and a few hours of my life were gone forever. Oh Ffff…iddlesticks!

Contest rules: Share your worst client horror stories

What’s one of your worst writing jobs? We want to hear about it. Share your worst client horror stories for a chance to win. Here’s how:

  • Post your worst client story in the comments below
  • Only one entry per person.
  • Contest ends: Sunday, June 16 at midnight Pacific.
  • We’ll review all the submissions and announce the winners here and via email in about a week.

Prizes for the worst client horror stories include:

Grand prize: A one-year membership in the Freelance Writers Den.

Runner up 1: A one-month membership in the Freelance Writers Den.

Runner up 2: A copy of the book: Start Here: 40 Freelance Writers Share How They Find Clients, Stay Motivated and Earn Well Today.

Good luck, everyone! And here’s to great clients to come.

And the winners are…

Grand Prize: Rhiannon D’ Averc

  • Lesson learned: Never, ever, under any circumstances, work in an actual content-mill sweat shop for room and board and low pay.

1st Runner Up: Courtney Ralls

  • Lesson learned: When it’s time to negotiate rates, stick to your guns, and never accept anything less than your minimum.

2nd Runner Up: Paul Haluszczak

  • Lesson learned: If you don’t have a contract, defined scope of work, agreed-upon rates in writing, and you’re getting the assignment from your client through a sketchy interpreter, you’re better off walking away.

What’s your worst client story? Tell us about it in the comments below for a chance to win.

Evan Jensen is the blog editor for Make a Living Writing. When he’s not on a writing deadline, or catching up on emails, he’s training to run another 100-mile ultramarathon

Join my freelance writer community: Freelance Writers Den



  1. astewart

    OMG, it’s really funny

  2. Tom Bentley

    A saga still ongoing: I wrote some property descriptions a while back for a fellow running some specialty Airbnbs. All straightforward stuff, with friendly exchanges between all. I’d never had any contact with his wife, when I got a recent phone call from her, many months since I’d heard from him. She asked me to write a GoFundMe page for her, to pay for a big fence on their property so she wouldn’t have to see the neighbor’s dogs.

    They and other neighbors had had trouble for a year with these marauding dogs and the dogs’ owner, but the most recent incident had the neighbor bringing the dogs onto her property, and one attacked and killed her dog. Their property is rural, and large, so the fence would be substantial, and require a lot of money, thus the GoFundMe page.

    Gruesome, but I understood the assignment, and agreed to it. Then she began a long story of how she and my original client had split up, over many complications, the dog’s death being one. I won’t go into the details, but it was convoluted, with many specifics you shouldn’t be telling a stranger, one you were hiring for the first time.

    OK, a flag there, and not just red, but burning. But I’d said I’d write her page, so I was going to hold to that. But I was unsettled.

    Two days later, her husband, my original client, called me. He immediately went into a long, rambling disquisition on why his wife and he had broken up, including the fact that he’d signed over the rights to their property to her, under great duress, in a quitclaim written by weaselish lawyers, that she’d been having an affair with an older man (80!) and a bunch of other things I shouldn’t have been told. But he said I should go ahead and write the GoFundMe page, because it had been his dog too, and she should be shielded from seeing the neighbor’s murdering dog.

    Multiple flags burning now.

    But I did write the page for her. Several days later, she called and asked me to send her the original copy for the Airbnbs, saying her husband was blocking her from using them and she was going to repost. Gong! Finally, I woke up, and said I couldn’t do that, and that I couldn’t be in the middle of the dissolution of their marriage, and didn’t want anything to do with work that was part of that.

    Two days later (you guessed it), I got a call from him, saying he was going to have to involve some private investigators, perhaps even the FBI, because she was violated his trademarks (and was trying to steal them) for another company he owned, and she had hacked a website he owned. He wanted me to write a long statement that was a summary document for the lawyer he was going to engage on these issues.

    I had to tell him the same thing that I told her, which was that I couldn’t write anything that was kindling in the fire of their flaming marriage. After many apologies (and more meandering details), he hung up. I still might—I’m stupid that way—write something for him on a different, innocent subject altogether, but it’s a Voldemort—she cannot be named or involved while discussing any writing to come.

    Perhaps not so much the client from hell, because they were mostly bedeviling each other. More like two clients from purgatory wanting me to join them. I’m not answering any Evites.

    • Evan Jensen

      Oh man. Nothing like being caught up in the middle of an actually Jerry-Springer-Live situation. If they’re paying you on time and decent rates, I guess you have to decide if it’s worth it to stick around and just say “no” to projects that are part of the drama instead of strictly business.

  3. Wendy Strain

    My ‘writing job from hell’ is an ongoing project at the moment. I feel the ‘come to Jesus’ call coming on already. The project started as a basic ghostwrite for an emerging personal coach. He had a MASSIVE manuscript already and wanted help trimming it down to size and filling in the gaps so he could use it to boost his credibility and for back of the room sales to help him book speaking engagements. We discussed what he had, what he needed (specifically the need to cut the manuscript down to no more than 80,000 words to compete in the mainstream space and to make it legible without all the word decoration – think italics, bold, underline, and quote marks in some combination on every other word, wish I were kidding or being hyperbolic – this comes into play later, I promise). He was thrilled with my proposal, we drew up a contract, met in person and had a decent personal connection (he is QUITE proud of his ideas which should have been my big red flag), and got started on the work. About two months into the project, he made it very clear that my cuts were too extensive and he didn’t want to change the content to such a great degree, and yet still expected the project to adhere to the proposed timeline as if all the extra work could somehow be squashed into the original anticipated time frame without any adverse impact (talking the difference between a 5,000 word chapter and a 100,000 word chapter here!). During our weekly 90-minute calls, he constantly talks over me, interrupts me when I try to answer any of his questions, and continues to demand that I deliver what he wants in the time he wants it without any consideration for the amount of work that entails or offering fair compensation for the scope change. At this point, I’ve already performed and delivered the amount of work promised under the original project scope even though it represents less than a third of his concept and he’s two months behind on his payments. He argues that he shouldn’t pay because we aren’t in keeping with that stupid proposed timeline (even after I pointed out that it is a ‘proposed’ timeline and it’s even labeled that it is subject to change as the project progresses). The contract also specifies that payment is expected on the first of each month and in advance of work delivered. We even discussed, in detail, the problem of the scope change back when he made it clear that he wanted basically an insanely long vanity book instead of a mainstream business book. My thought at the moment is not to deliver any more work until he’s caught up on payments and to try to have another frank discussion with him about the extensive scope creep from the proposal and contract assumptions.

  4. Danielle

    My worst client story involved a past relationship. My boyfriend and I decided to partner up because he was good at finance, while I was great at developing content. His job was to make us more money by studying the writing market in our country. Our goal was to start a writing business together with me as the first writer. We were referred to a real estate client and I had already prepared the proposal with a fair retainer fee. I was supposed to populate their real estate website with the entire country’s listings. Sounds like an awesome gig, right? I was new to the local market, so I did my best to offer a reasonable rate from an unknown entity. I was competitive, but my offer was still attractive. Here’s where it gets crazy. I presented the content strategy and they loved it. We then got to pricing. I offered a suitable amount with room for negotiation. Unfortunately, the client kept cutting down the strategy to lower the price as well. I agreed, so long as it was still in the realm of my minimum allowed rate. Still, I was being backed into a corner. This was my first face to face negotiation with a client. I knew that I shouldn’t budge because I knew the worth of the work they were asking for. The clients then started that thing they do, where they get quiet and keep looking at the same piece of paper, playing freelancer chicken. Suddenly, finance ex-boyfriend spoke up and made them an offer they couldn’t refuse. I offered a three-month retainer. The ex counteroffered with a 50% slash and a longer retainer contract. They sealed the deal while I was still in shock. When we left the client’s office, I asked my then boyfriend, WHY??? He said that’s how services are priced here in our country. If we didn’t offer that, they would have never accepted, he said. I told him that it wasn’t true – that I made ten times as much for easier projects. He convinced me that it was good for our business portfolio. We already signed the contract because I was too embarrassed not to. That was the beginning of the worst six months of my life. I had to work full time for them for scraps. Here’s the kicker. When they launched, they didn’t even use any of the copy I gave them. They decided to hire an on-site copywriter. The lesson I learned here is that rate culture will kill you. The people you trust will make big mistakes that you will pay for. I was young back then and held on to the belief that this is a great addition to my portfolio. We’ll be racking in international clients once we get this done. Now, I can’t even show the site because none of my work was used there. Fast forward two years later, the client contacted me and asked for the same work and I gave them the increased price citing inflation and market rate increase. I know, it was BS. But that’s the only way people here understand why rates increase. I knew they wouldn’t go for it and I told them I’d find someone else willing to do it. Big surprise. No one wanted it. It’s a long story, but let’s just say my country is messed up when it comes to writer’s rates. Aside from getting swindled out of $5,000 from a previous client(a boring story compared to this one), it was my biggest lesson to date. Since then, I’ve avoided clients like that and I kicked my ex out of future negotiations. Side note: We didn’t break up because of this. However, he did learn a lesson in freelancing and that is we should never accept rates like that ever again, even with the promise of continuous work. I already had clinical depression and I relapsed because of that project. My ex understood and acknowledged that I love the work I do, but not like that. That project made me hate writing. Now, I love it again because I make my own rules and choices.

  5. K. Wright

    My worst client experience also happened to be one of my first when taking a step into the world of freelance writing. I wanted to be published with an online publication besides my own blog to build my portfolio, and a friend connected me with her brother who worked for an online magazine.

    We corresponded and agreed that I would write 12 articles for the magazine, one per week. The work was unpaid, which I was okay with since I was mainly looking to gain the “experience,” but he did mention that if the magazine liked my articles, they would consider paying me once the “trial” period was over.

    I diligently wrote the articles and submitted them on time every week. (And I use the phrase “on time” loosely since there were never any real established deadlines.) The editor gave very little feedback on the first couple pieces I sent in, then stopped responding altogether whenever I would notify him that the most recent article was ready to be published.

    After completing the 12 articles, I contacted my friend’s brother about the potential to continue working with the magazine, but on a paid basis. After a few days, he offered $25 per weekly article. By this point, I was beginning to realize the value and time that went into my work and I politely declined.

    I recently discovered a bonus to this whole ordeal when going to their website to save some of my work for future reference. They had switched out my byline with another contributor’s for one of the articles I wrote! I would say unbelievable, but after the poor business practices I experienced with them, it’s actually very believable.

    Let this be a cautionary tale for any new freelance writers: ALWAYS get a contract for any work you do, DO NOT work for free (the exception should be one or two unpaid articles if you need to build a portfolio, not 12), and save your work right away should any shady client plan to steal it later down the line!


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