Essay Contest: Tell Me About Your Most Hellish Freelance Writing Jobs

Carol Tice

Most Hellish Freelance Writing Jobs: An Essay Contest. had a client who was a total nightmare? If you do even a handful of freelance writing jobs, it’s bound to happen.

They don’t know what they want. Their deadline is yesterday. You’re getting gang-edited by a team of five.

Since I’ve been at this a long time, I’ve pretty much had every flavor.

But what’s your worst story? I’ve decided to collect them all here on the blog comments (yes, they’re open again for this post!), so other writers can learn the red flags to watch out for.

What’s in it for you? You could win a free year in my freelance writer community, among other goodies.

Contest rules

How do you win? Here are the rules:

  • Keep your essay to 100 words or less.
  • Describe your worst client experience.
  • Post in the Comments below, or on Facebook or LinkedIn (look for the post graphic from this post on both social-media platforms and comment on that thread).

You’ve got until July 10, 2018 to enter — I’ll announce the winner on Wednesday, July 11. Which not coincidentally is Freelance Writers Den’s 7th anniversary! Here’s what you can win…

The booty

What can you win, for sharing the story of your most hellish freelance writing jobs? Here’s the rundown:

  • Grand prize: A free, 1 Year Freelance Writers Den membership ($300 value)
  • 1st runner-up: 1 month in the Den + A set of 4 Den ebooks on blogging and freelancing + complimentary copy of the Den Basement Tapes ($100+ value)
  • 2nd place: 1 free month in the Den + Freelance Business Bootcamp e-book + A copy of the Den Basement Tapes ($75+ value)
  • 3rd place: 1 free week in the Den + A copy of the Den Basement Tapes ($50 value)
  • Honorable mention: Complimentary copy of the Den Basement Tapes ($29 value)

There you have it — an array of helpful freebies ranging from community learning to e-books to podcasts.

What’s the Den Basement Tapes?

You might be wondering: What are the Den Basement Tapes, anyway?

Well, we develop new content every month in Freelance Writers Den — and after 7 years, the virtual shelves have gotten crowded.

From time to time, we move some podcasts to our basement archives. These are great, classic trainings, but they’re no longer available in the Den.

Just because…300+ hours of trainings is enough! Don’t want to overwhelm members with too much stuff.

Now, for the first time ever, we’re making those Basement Tapes available to the public in a flash sale for just $29. Here’s a peek at the five podcasts in this Basement Tapes offer:

  1. Making Money as a Ghostwriter with Kelly James Enger: Longtime Renegade Writer Linda Formichelli hosts Enger for a chat on breaking into this lucrative field.
  2. Motivation and Productivity for Freelance Writers: Linda gets productivity tips from expert Max Wirestone and Mini-Habits author Steven Guise.
  3. The Business of Freelancing with Princess Jones: Linda talks about how to run your biz right with the successful blogger/author.
  4. How to Write Case Studies with Casey Hibbard: Den Mother Carol Tice (a/k/a me!) talks with the top case-study expert on how to break in, writing tips for case-study excellence, and how to price these projects.
  5. Freelance Writers Den Success Stories: Listen in while I get four successful Den members to spill all the details of how they’ve become more productive and grown their income.

Yes, for the first time ever, we’ve made a hand-selected cache of our finest Den events available for nonmembers to learn from, for just a few days only.

Interested? Share your mini-essay below in the comments to win make your copy of the Den Basement Tapes free. Or to win Den membership access and/or useful e-books. Look forward to reading!

UPDATE: Congratulations to our winners:

  • GRAND PRIZE: Diane Young
  • 1st Runner-Up: Charmaine Engelsman-Robins
  • 2nd Place: Derek Thompson
  • 3rd Place: Heather Ritchie
  • Honorable Mention: Jessica Sz

What was your most hellish freelance writing job? Describe it in 100 words or less in the comments below (or on Facebook or LinkedInfor your chance to win our essay contest prizes.

What kind of freelance writer are you? (New Writer, Mid-Career Writer, Just Thinking About Writing?) Tell me and get a free custom report. Get Your Report.


  1. Derek Thompson

    I landed an editorial job for a high profile, dream client. Although I upsold for an additional word count, each round of revisions provoked entirely new sections of material. Add in email failures (his end), missed deadlines (him again) and weekend working to suit his revised schedule. Bad enough that I got royally hosed on the price, he even wrote an online testimonial citing my ‘extra work at zero cost as a goodwill gesture’. Salt to the wound!

      • Derek Thompson

        Yep, as Frankie Valli never said, ugh is the word!

  2. Mark Onuchi

    Writing for me is a passion and for most of my clients, I always have their briefs clear in my head.

    A friend had recommended me to this middle aged business tycoon, initially it seemed a pleasant voyage. Then he suddenly began to blow hot, everything went awry…like something snapped! The idea was no longer clear in his head, he had lost the plot and he wouldn’t let me give him direction. I tried all I could to no avail, then suddenly his sanity returned! Everything aligned like nothing ever happened; put the thoughts together he was home with it, paid me and I was gone!

    • Carol Tice

      Ha — when that happens, I think…cocaine. I had a boss like that when I was a legal secretary, he’d be totally rational and then suddenly…nuts! Then, back to rational again.

  3. Chanoa Tarle

    She was a sassy realtor with an agency that shared her name. I was a first year freelancer. It was fun – at first.

    She was my highest-paying client and it was the kind of content I would have (almost) written for free. The fairytale ended fast. She and her perpetually CC’d, one-named assistant questioned everything. Every word and comma of my ghostwritten posts were brutally dissected. It was micromanagement like you’ve never seen.

    I took a break when a loved one suddenly passed away. When I got back to work, she turned completely cold and ignored me.

  4. Tom Bentley

    I wrote promotional copy and edited tech docs for a company that billed itself as having made “revolutionary” (at least for the year 2000) breakthroughs in video production and streaming, and some early augmented-reality technology. They hosted a bunch of client and potential client websites to show off the tech. I was busy writing documentation for their demos, which showed off the placement of crude bitmapped objects in virtual rooms that the user could interact with. After a couple of months, I finally visited the live sites: they were ALL some version of live or taped porn. Erase from résumé.

      • Charmaine Engelsman-Robins

        “Erase from resume.”

  5. Beth Tyler

    I knew on the phone that this man would be my nemesis. But like a dumb, desperate freelancer, I took the job anyway, which was advertised as a one-day task due by 5:00.

    I rewrote several marketing slides for a whopping $50 gross. The client’s general finicky nature and continuous real-time requests for revisions made the job last several hours. I finally finished and was paid immediately.

    The next day, the client digitally stalked me and told me I hadn’t finished the job because he didn’t like ONE SENTENCE. He filed a dispute against me, and fortunately, I won.

  6. Martha Verne

    I was ghost writing for a hairstyle blog on an online site, and the client wanted me to do an article covering styles through the new year as well as how to do the most popular styles at home. As it happened, one of the styles involved old hollywood circa 1930s Fingerwaves. So I turned the piece in, and back comes an e-mail saying that she no longer needed my services due to plagerism and that she would not be paying me for my work ! Looking at the screen shot she sent of the supposed plagerism, low and behold it was how to do a Fingerwave. Now, there are only so many ways to describe how to achieve a Fingerwave ! I wrote back and explained this to her..(english was not her first language) and she agreed to let me try again. This went on for several attempts and it still came back plagerized everytime, again.. only so many ways folks-of course it is going to hit on a plagerism program ! She still accused me and still refused to pay me, so I had to get the site we were on involved-but I finally got my money!

  7. Bethany Widdicombe

    In the cold of December, I kept receiving calls from one of my clients. I had been working on ghostwriting articles that had his name on it. He would aggressively critique the articles but he insisted he liked my work and wanted to keep me on. He kept promising to raise the payments after a trial period, but instead spoke to me in frightening tones over the phone about tasks and never paid for my time. I was new to freelancing and felt too scared to quit it, but luckily, the contract ended and I never answered any more requests.

  8. Is Andrews

    My client nightmare is still going on!

    As another writer has already said, the moment I got the phone call, I knew in my bones this was going to be a hiding to nothing. But he sounded like a young, enterprising startup with a good idea and little capital to push it. He suggested a pretty sharp overall project price for a seven-instalment piece of marketing copy to cover different aspects of a new app and accompanying website. As we agreed there would be a fair amount of overlap, I decided that the paltry sum for the first few pieces would aggregate over the whole project to be a reasonable amount for my work. Still not a goldmine, but a fair wage to be paid for helping someone who needed a leg up.

    Then the missed deadlines and long email silences began. There would be weeks going by with no comments, and my work seemed to be vanishing into the ether. Every time we spoke on the phone he was friendly and amenable, but I began to get the sense that he now had other collaborators on the project, and perhaps some investors. He appeared to be spending vast sums of money on research and marketing trips abroad. So much for my earnest go-getter!

    I completed the last two instalments of work, and submitted my final invoice, having received a couple of payments already for the previous five. Nothing happened. I gently prodded for my cash. Still nothing—and then I receive a bunch of new work, but the client expected it to be covered within the original agreement, “because of all the overlap”! Gah!

    We set up a Zoom call to discuss this new brief, and the issue with payment. He was friendly and promised to pay up, asking for new quotations for the work… but his brief was hazy and unclear (just as the last time). I tried to explain to the client that if you don’t know what you want, you can’t be mad if you get what you asked for; he continued to waver and potter around a variety of different ideas and requirements, much as I tried to pin him down to a concrete proposal. In attempting to get a better sense of what he wanted, the client told me that I would be able to see what he meant if I checked out the app and website, because they were now up online, using my still-unpaid-for copy!

    The following day I received an email telling me that his investors wouldn’t stomach my final fee. Oh, and his marketing partners agreed that there was too much repetition to justify the cost. (But he still wanted that new quotation.)

    The super frustrating part is that I think he’s somehow under the impression that I’m trying to pull a fast one on him, and he simply doesn’t see the gross unprofessionalism of quibbling over payment after the work’s completed, or of agreeing something on the phone and then reneging over email just hours later.

    This all happened in the last couple of months—I continue to chase my final payment!

    • Carol Tice

      Ugh — this is why final payments have to be due net 14 days from delivery, NOT acceptance. They can always dither forever about the draft!

  9. Shane Cheshire

    It was a sultry July morning, the humidity was so thick you could float upon it. My client and I sat in the blazing heat on a coffee shop sidewalk; He berated me about the copy I had for him.
    As he leaned in to curse me, during this hellish attack, sweat from his greasy pufferfish face dripped into my expresso; I was mortified to hear F*&% this piece of S#&^ screeched at me. Then in his last hoorah, he leaps up throwing the chair behind him, as well as, and shouted: “I wouldn’t wipe my ass with this shit!”

    • Carol Tice

      Srsly? I find this story a little fascinating, since clients who’re mad at us don’t usually take the time to go meet up with us at coffee shops. That’s sort of the interesting angle here!

  10. Charmaine Engelsman-Robins

    During a financial drought an upscale city magazine assigned a health article unlike their usual plastic surgery pieces; something for families. I wrote about kids and National Burn Month, including info from national authorities and experts. It finally hit stands … no story. I triple checked and hastily called the editor who distractedly said: “Oh, I thought I told you I pulled that…” Uh, NO! Not only did I have to call all those I’d quoted and explain, but the financial hit put me over the edge I’d been teetering on and I lost my home of 17 years.

    • Carol Tice

      So sorry to hear! Writers need an emergency fund. And…get paid on acceptance rather than publication. 😉

      • Charmaine Engelsman-Robins

        I’m with you all the way on both suggestions, Carol. Just trying to figure out how to accomplish either one: Mags that pay this much locally (usually $800 – $1200 per piece) have no shortage of writers lined up and willing to wait for pay; the emergency fund can’t be established til all the utilities are on again … lol. Thanks.

  11. Philip Verghese Ariel

    My client a prestigious company having a wonderful business online approached me for a prestigious writing order through a third party.

    Knowing the company’s name activities I took lot of pain to make it a best write up and to my utmost satisfaction it has come out well.

    To my belief, it was one of the best I ever created with a lot of illustrations, graphics, screen shots and other images.

    But sad to say that even after submitting the final product there is no response from the company or the agent.

    Now several weeks passed by and still hoping for the best. In fact that was a deal thru a third party agent and I believe that something happened in between!

    Anyways, I am yet to hear from the party and yet to receive the payment.

    My repeated queries are unheared or not responded.

    This is one of the hellish freelance writing experience I ever had.

    Lesson learned.
    Do not go thru a third party agent!
    Take 50% or more advance before delivering the final product.
    Philip Verghese Ariel
    The multilingual Freelance writer

    • Carol Tice

      No…take a 50% advance before you START working, Philip. That’s pretty standard practice with legit clients.

      • Philip Verghese Ariel

        Yes,Carol, I did a mistake here thinking that the client is a reputed company and thought they respond well. I send another reminder and waiting for their response, if they do not respond, I will send a final mail saying, “If you respond to my queries I will go public with my experience with you”
        Is that ok Carol?
        Or how long I have to wait for their response?
        Thanks for your valuable feedback.
        Have a great week ahead.
        ~ Philip

  12. Heather Ritchie

    My experience started with Upwork. I was hired at the most ridiculous rate of $8-$10 for a 1,000-word blog post but I was desperate to work from home. It was a husband and wife team and while they were nice, he and I related more because of our backgrounds.
    They ended up hiring me on as an Editor for $700 a month and I had no idea what hell I was in for. I mostly worked with her and there were hundreds and I mean hundreds of articles for us to edit and it was only HER AND I! It got to the point I hated hearing my inbox noise ding.
    She got frustrated when I wasn’t available every day and kept returning my work saying that my editing wasn’t good enough. The writers were horrible and its no wonder when you pay like that. They said that it was a good rate and of course by then I found people like you who opended my eyes.
    They didn’t believe me that I found someone that I was writing for getting paid $.05 a word (my current employer). They said that if I was getting paid that, that it was absolutely the most I would ever get! GEEEZZZZZZZ

  13. Ash

    Most hellish? Well, the most interesting one was this guy who owned a cosmetic store. When he didn’t clear the payments even a week after the deadline, I decided to send off a reminder. His reply in all caps — “WERE YOU RAISED IN A BARN? IT’S ONLY BEEN A WEEK.” Oh!

    The email accompanied another one from PayPal though, “Your invoice has been paid.” So there wasn’t much to fight for. I just sent them a “Thank you” email ” …from the Toy Barn.”

  14. Elena Knicely

    Sometimes, the most hellish clients escape the “textbook” definition. Mine lacked the obvious signs, or I would have fled!

    Bob was a pleasant client who agreed to pay $700 for a website project.

    Once I began, I realized that it required “expert” knowledge and more research than I ever imagined.

    I fell behind.

    Bob was understanding. Yet, he added more work and wouldn’t change his deadline.

    I lost hours of sleep and got a 2-star review from Bob. He didn’t say why.

    On the contrary, he’d always complimented my work.

    Bob was a devil under a shiny robe.

    • Carol Tice

      Moral of story: Don’t write for mass sites that give you ‘ratings’ — wish I had a dime for every writer whose career has been ruined by one of these scenarios.

      • Elena Knicely

        So true! I didn’t want to go over the word count on the story. The good news is that I quit the platform afterwards. I learned that if I want quality clients, I need to market my business and identify a target audience. I’m glad that this happened when I was fresh out of school. The experience enabled me to branch out, and I think your website was one of the main forces that encouraged me to build my own career from ground up… thank you.

  15. Stephanie Mayberry

    Trying to keep this at 100 words was tough but here goes.

    I got a gig to write a “99 second script” for $500. Not great, but OK. I got the 50% up front and dove in. The client provided an outline so I followed it explicitly. I expected positive feedback. Not so. He had named prospective customers as his audience, but he launched a full scale attack on me because he wanted it aimed at investors. So I rewrote it for this new audience only to be accused of adding to his outline. The only “additions” were transitions from one of the facts in his outline to the next. He was abusive, condescending, cursed at me, the whole bit. Then he ghosted me. I never saw the other 50%.

    But I’ve never seen him again, so it’s all good.

    • Derek Thompson

      Hi Stephanie, it sounds like your client wanted two scripts for the price of one and then only paid a quarter of their worth. :o(

      • Stephanie Mayberry

        Yeah, that was kinda the feeling I got too. He was scum.
        I realized that I would never ever please him.
        I lived in an abusive marriage, I quickly recognized the signs of an abusive personality.
        He was horrible, abusive, and cruel.

        • Derek Thompson

          The main thing now is that we all learn from such experiences, and from one another’s.

          • Stephanie Mayberry

            Yeah. I created a very detailed project brief that the client has to sign off on. Changes to the brief mean a reevaluation of the price.
            So far, it’s working really well.
            I just can’t deal with someone cursing at me. That just goes through me like a shot – especially when I am doing exactly what I am supposed to do.

  16. Faiza Mostafa Taha Yasin

    I am as a freelance content writer for almost a year within a company. We wrote a strategy for a so-called fashion designer in Egypt and for sure asked for her approval before launching (as we would do for every client). Lucky me I already have a friend within this world and I found out she basically stole a design and put her name on it. Simple right? Well, it turned out after weeks of working for her, she backed out last minute after the launch within days and got away with my words.

  17. Mohammed Montaha Hossain

    I began freelance writing a year back on Being one of the biggest content mills on this planet, I soon worked my way to a client who ordered me to write 500 word articles on various for only $1. It was soul sucking and exhausting to work at that rate, but I was desperate enough to take up that gig. It was hard to satisfy that client; he demanded quality content for less than the price of a Big Mac. Eventually I gathered up the courage to quit that gig.

  18. Tracy Brighten

    I’ve been fortunate to write and edit for inspiring and appreciative clients. My bad freelance experience relates to a platform rather than a client. One year ago, I joined the professional section of a freelancing platform. A few months ago, my excellent support manager left. I wonder how I grow my professional business in an environment that now seems to lack transparency. I feel manipulated by a system where throughput is the priority. The challenge is to recognise when we’re not thriving and to find gig sources that foster self-respect and reward dedicated customer service and high-quality work.

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