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. Mel Francis

    I was employed by an NGO/non-profit organisations to produce them copy for a fundraising website, and to develop a campaign to promote the site. The NGO in question had been used to asking for a bit of money from enthusiasts of the particular kind of wildlife they dealt with. The brief was to increase their audience, and to enable them to reach out to, engage with, and ultimately fundraise from a much wider audience.

    In my response to the brief, I outlined the action pyramid, that took them from outreach to cold audiences right through to how x% of this new group will click through to read information , and that of these people to expect only y% of people to actually give some money in the first instance. I also outlined a funnel to keep reminding people they were there, to provide engaging content, and how to keep giving people calls to action up to and including donating money. I was very clear in interview, but not in writing, that I was not a web designer, and that if they also wanted the website designed that I would be able to recommend other professionals, but that I would not be able to undertake that myself. In hindsight, a big mistake.

    They seemed very happy with my proposal. I spent a while in the office to get to know the subject experts. Their expertise on their chosen subject was impressive, but definitely bordering on nerdy, with lots of acronyms and in-jokes.

    Anyway, I really slaved over their copy, outlining the issue, and highlighting interesting facts about certain species, to help engage new audiences. I felt, and still feel that the issue was important, and had much broader impact than the simple preservation of their key species. So I included a lot about what their habitats do for humans in my initial landing page, and in some e-mails I produced.

    It turned out that the team I was working with also expected me to be able to develop the back-end platform through which they could receive payments, despite several reminders of our agreement, and actually offering them contacts of people in my network who could help them. In the end, in order to be able to get on with my writing, and still meet immovable launch deadlines I Googled ‘best WordPress templates for fund-raising’ and sent them my results. By which, I mean I sent them the URL to the Google search and told them that [template name] seemed to have the best reviews and that they should make sure that it was suitable for their needs. They went with my ‘recommendation’ with no further research. They complained when I couldn’t do much more than activate the template, and talk to the producers via their support system (e-mail based).

    Then came their edits to the copy. As well as being used to writing everything by committee, they had not really grasped the fact that they wanted to engage with a much wider audience, so they kept feeding back things like ‘this is far too basic for our current donors’, ‘everyone will know the information on this page, why is it necessary?’ and many similar things. They also wanted me to edit the landing page – where I was supposed to be outlining the issue to a non-expert audience – to two sentences. They told me the one I had written was ‘boring and condescending, everyone knows this’ and wanted to insert a whole load of scientific data without much explanation into the whole text willy nilly.

    We had a crisis meeting, where I checked the brief, and that the important part was that they wanted to reach out to new audiences. I thought I had finally got through to them. I had to bring all of my conflict resolution and mediation skills to bear in this meeting. I finally thought they understood why I needed to explain things and I found a compromise on how to present their data in a way the new audiences could manage.

    We signed off the work. The only good thing about this process was that I was paid.

    Six months after I had delivered the work, I got an angry call from the Executive Director. She had just had a very difficult meeting with the Board of Directors, who were demanding to know why the website had not shown an increase in the funding. She also yelled at me about the WordPress template having been too difficult to use, so why did I recommend and set it up, and a lot of other stuff about why should she be held to account for my poor work (which she had signed off on). During this call, I logged onto the fundraising site to try to explain something, only to find that what they were using was not the copy I had delivered them at all. Someone had changed it, so that it addressed their usual audience, and contained all the inaccessible data I had strongly advised them against using in the format in which it appeared. It turned out that they had changed it shortly after launch, but I was somehow still responsible for their lack of results.

    So I have learned to be much firmer on not agreeing to anything to do with web design. I’ve also really firmed up my process, so I get organisations to agree that the time for them to input on content is at the ‘detailed briefing’ stage, where they can say what information to include. After this, I will write the copy, making sure the content is delivered with a ‘common voice’ to avoid audience confusion. After that I don’t allow substantive edits without renegotiating the price (both of these tricks I learned via some online seminars offered by Carol and guest lecturers). I am still at a bit if a loss about how to deal with being the scapegoat if they don’t use my copy, but still want to yell at me for their lack of results.

  2. Courtney Ralls

    My worst writing job was my first one as a freelance writer. I took the leap and started a content writing agency and I was placing ads everywhere – including the dreaded Craigslist. I put up an ad for $5 advertising my expertise in writing for businesses and I got a bite back from a man who branded himself as a financial literacy coach and life coach.

    Well, we met up the first time at a Starbucks because he refused to email me the work details he wanted completed, which I should have taken as the first red flag. He wanted his entire website content re-written to clearly state his personal story and how he can help others with money and real estate investment as income. I was pretty confident I could perform the job because he already had existing content on his website it was just very poorly written. After our meeting I promised a first draft of his website content.

    Fast forward to sending him the first draft, he received it and immediately fired back with remarks about how I didn’t do much to change the copy. He said that my work was not up to par with others in his industry although his website was riddled with incomplete sentences, punctuation errors and all around didn’t make sense. Even though I was steaming I agreed to let him write a draft and I use that as a second draft for him. He did not use email so he wrote out what he wanted the website to say and I took it home and typed it up, refreshed it for SEO and grammar purposes and met back up with him to show him.

    The second draft was still not to his satisfaction. After I sent him the invoice he told me he was wary to pay because I simply did not write anything I just wrote what he gave me (which is what he asked for). After meeting up with him several times and accepting and transcribing his notes of his website content he ended up paying me half the amount I asked for. I just chalked it up to my first experience and moved on.

    I haven’t used Craigslist to advertise since.

  3. Nora King

    My first professional writing project was with my local free healthcare clinic.

    (Prior to January 2019 in Virginia eligible persons were those with no insurance options, even excluding those with Medicaid. Since January 2019 Medicaid clients are served there too).

    I live in a rural community and it has been difficult to find an opportunity to work face-to-face with a client while learning the craft of copy writing.

    I volunteered for this project after the clinic published an article in the local paper, featuring a volunteer who was celebrating 10 years with them. I thought I too could volunteer to do a project to get copy writing/marketing experience.
    This was in June 2018, a year ago.

    The director there was very excited with my proposal and stated she wanted to send a fundraising letter. She showed me one they had sent several times before. The quality of it, including the graphics, was so poor I would have been embarrassed to send it. We talked about what we could do and both of us were excited to get started.

    She told me up front that she would be away for several weeks, so I was not surprised when I did not here from her for a while. I made myself busy by conducting two case studies, one was with a former client and one with a member of the Board of Directors. I completed the rough draft before she returned and had it ready to submit when she returned.

    This is when the fun began. I sent an email with the draft in a .pdf attached. Then I set another email.

    Then another.

    And another.

    This went on for several weeks.

    I then received an urgent phone call from her. She had a board meeting scheduled for that very afternoon and needed the draft “ASAP”. I sent it to her again.

    I did meet with her at least twice after this time.

    During these 1-1 meetings I stressed that we were approaching the last quarter of the year and that this is the time when the United Way starts their annual fund raising campaign. I reminded her that the United Way asks’ it’s recipients not to conduct their own fund raising during this time, as this would likely prove ineffectual for all campaigns being conduced.

    I also provided other feedback that I thought was important for her to know and volunteered to do another project, but she expressed little interest. This feedback was that the clinic’s stationary/letterheads were old copies of what had originally been colored copies. They were now gray/black/scratchy and difficult to read.

    I offered to create new Windows 10 copies with original greyscale graphics and using the cliniic’s new logo, this because black/white copies they make on a daily basis would be cleaner and so they could do away with the scratchy logo on the stationary they are currently using.

    Not interested.

    I also stressed the importance of having professional-looking letterheads to use for client-related documents, such as release forms, etc…

    Keep in mind that I was not charging anything to do this.

    Her primary interest now was that I volunteer to provide counseling services. (I am a Licensed Clinical Social Worker turned copy writer). She informed me that a grant the board had applied for some time ago had come through but that they still need volunteer counselors and case managers. It was after the board meeting that she lost interest in the copy writing project.

    I believe I created some anxiety in my feedback to her, this because I asked if the agency was providing adequate malpractice insurance for professional volunteers, this among other things.

    I could go on, but I’ll say that I disbanded the project in December after having sent another series of emails in which I received no response.

    As noted, the clinic started seeing Medicaid clients in January 2019. In order to be in compliance with the federal government and with the state of Virginia, the Board and the director would have had to find someone to meet and exceed my recommendations to her.

    During the winter I saw the lady I had interviewed for the case study in the grocery store, this the member of the Board of Directors. She asked me “Where have you been? You just disappeared”. I told her of my efforts to stay in touch. She told me she would “…have to check into this”.

    Lastly, and just a couple weeks ago, I was in the clinic for another reason. The director came into the lobby where I was sitting. She literally tip-toed in front of me, avoiding me while going to see someone else. she stayed just a few seconds then spun on her tip toe and back out the door again.

  4. Rhiannon D'Averc

    My worst writing job was actually my second ever – and I put a lot of it down to the fact that I was so inexperienced at that time.

    I was headhunted out of uni by a culture and tech blog who wanted me to write for them. One of my fellow writers there also worked for an SEO company that was local to where I had been studying, so I ended up getting a job there.

    The boss was a penny-pincher from the start. Accommodation was included in the job, so he didn’t have to pay as much in wages (the flat was really poorly maintained and there were up to six of us living together at any given time – all employees of the company; at one point he even converted the living room into another bedroom to squeeze us in). He also had us all on “freelance” contracts so he didn’t have to pay as much in taxes – knowing what I know now, it was definitely NOT freelance work!

    I went in there being told that I would have to write about 10,000 words a day. That was really daunting, but I gave it my best shot. The work was easy, but mind-numbingly boring. 500 words on ‘best online casinos for poker’; 500 words on ‘best casinos for online poker’; 500 words on ‘top online casinos to play poker’ – you get the drift.

    Over and over and over again, poorly-chosen keyword stuffing in articles that were always too short to make any real point but so long it felt like they would never end. I would get to the end of each day feeling like my brain was melting.

    I was so eager to impress that I ended up doing an average of 14,000 words a day during my first week. Guess what? That became my new minimum… for no increase in pay.

    By the time I decided to leave, I was doing a minimum requirement of 18,000 words a day and when I asked to bring that figure back down a bit, he insisted I take a pay cut. I moved in with my partner, went on holiday for two weeks with my family where I was supposed to be working remotely, and while I was there, sent him an email saying I was quitting.

    Since he had me on a freelance contract I was able to leave immediately. I got my tiny bit of revenge by leaving him in the lurch without anyone to do my work.

    These days I average around 4,000 to 10,000 words a day depending on what I’m working on. I still can’t believe I was typing that much every day. I kept a running count and I was well over a million words when I left them!

  5. Janet Rae-Dupree

    I’ve had my share of writing gig nightmares but the absolute worst was the cover story from hell.

    I was thrilled to be commissioned to write a cover story for what had been one of the leading business publications in Silicon Valley. Sure, it had fallen on hard times after one of the tech bubbles burst, but it was still churning along, raking in cash from conferences and publishing fat magazines every quarter. They promised $3,000 for a 2,500-word main story and 500-word sidebar with a $250 bonus thrown in if I could hustle and get it done — including edits and approving page proofs — in the three weeks leading up to Christmas.

    I dropped everything to focus exclusively on this package. I endured three rounds of edits, took phone calls on weekends and nights, huddled at the back of Cub Scout meetings, stepped out of other meetings, was at their beck-and-call (and I didn’t do any of my traditional Christmas prep) so that I could get this puppy done.

    Everything was approved on Dec. 22 and I eagerly awaited seeing the magazine in January.

    And I waited.

    And I waited.

    I invoiced them, of course. The response?


    February rolled around. No sign of it. So I invoiced again and left gales of voice mails.


    March came and went. I invoiced a third time, called repeatedly, left voice mails for editors up and down the chain of command.


    At the end of March, I heard through the grapevine that they had been evicted from their offices for non-payment of rent. I tried calling again. All of the office phone numbers had been disconnected.

    But I had the primary editor’s mobile phone number. I dialed and prepared to leave yet another voice mail. But he picked up.

    “Oh, yeah, hey, sorry to have been out of touch. Yeah, there was a cash-flow issue that cropped up and so we’re looking for new offices, but don’t worry. We’ve got an investor stepping in next week and we’ll be able to publish and get you paid.”

    I’m glad to hear that, I told him, but if things don’t work out there’s still time for me to take back the story and sell it elsewhere to cut my losses — but only if I can get it placed by the end of April. The news hook will go stale after that.

    “OK, yeah, great thinking! Let’s talk next week!”

    A few days later, I (and the rest of the subscriber base) got an e-mail containing a snazzy digital version of the magazine. There was my cover story in all its digital glory. The e-mail announced that the printed version would follow shortly.

    It never did.

    Of course, now that the story had been published digitally, no one else would buy it.

    I invoiced again, and all of my e-mails bounced back as undeliverable. That editor’s mobile phone number? Disconnected.

    When I went to the courthouse to check into filing a small claims case, I discovered 17 or 18 summary judgments already existed against them over the previous year. Seems they never bothered to send anyone to respond to those filings.

    Did I learn anything from all this? Yup. Never, ever give up Christmas or family time to work.


Submit a Comment

Your email address will not be published. Required fields are marked *

Related Posts

WordGigs Review — Is It Worth It? (2022)

When it comes to finding writing gigs, there are a million places to choose from. You might be looking for a WordGigs review and trying to figure out whether you should go through the application process to become a freelance writer for their site. This WordGigs...

How to Get Into Gonzo Journalism

If you wanted to learn about how to get into gonzo journalism or the history behind it, you've come to the right place. Originally credited to Hunter S. Thompson, gonzo journalism is the style of writing where you're covering a topic or event, but you're mixing your...