The Sad Tale of Your Worst Writing Job Ever [An Essay Contest]

Carol Tice

The sad tale of your worse writing job ever [An essay contest].

Ask any writer about their worst writing job — and they’ve got a story to tell.

If you’re a freelance writer for any length of time, some gig will go sideways on you. That’s just how it is.

The key is not to see that worst-case experience as an indicator of your skills, or a referendum on your future potential as a writer.

It’s just…business. Things go wrong. Misunderstandings happen. Everybody has a bad day.

Because so many writers seem to be devastated when they bomb at a gig, I thought it might be useful to collect worst-client stories and let writers compare notes. I thought we could collect them in the comments on this post.

So I’m having a contest! Details are below. But first, I thought I’d kick this off by sharing my own worst writing job stories.

I’ve been at this so long, it’s hard for me to pick an all-time worst writing job. I’ve got five nominees — maybe you can tell me.

  1. The brushoff. One of my first business writing clients agreed to $600 for a brochure — then decided to simply not pay me. “I feel really good about my decision,” she blithely told me. It was the ’80s. Feelings were big.
  2. The blowhard. Was it perhaps the guy who wanted to shout all his instructions to me on speakerphone, while he walked on his treadmill and listened to Rush Limbaugh at full volume? (This was a short relationship.)
  3. The tech-picky. Or maybe the woman who fired me from a Microsoft-contractor writing gig when I told her my home scanner was broken. (“You don’t understand how I need to work,” she told me.)
  4. The scope-creep kings. Then there’s the company that told me they wanted the same sort of blog posts I was doing for Entrepreneur — but turned out to really want posts that were twice as long, in which I ghostwrote for them in the voices of several different team members. When I suggested the fee should be quite a bit higher, they stopped returning my calls.
  5. The non-starter. Finally, and most recently, there was the company who wanted a quality-of-management research report for $3,000. These involve developing hundreds of leads you contact, and getting at least a half-dozen of these former employees of a publicly traded company CEO to tell you what they thought were the business leader’s management strengths and weaknesses. They approached me last summer. I’d done these before, and liked the work.I worked on this for over a month, and couldn’t get one single person to talk to me. None! Total loss. The company was understanding, and nice enough to let me keep my deposit because they knew I’d put in about 80 hours of work on it, and I offered to share my notes so the next writer wouldn’t waste time calling the same no-talkers I’d hit.I felt…awful. I never say die on an assignment — I always keep going and get the job done. And this one defeated me. Did I mention that they courted me for three months before we finally inked this deal? Yeah.

If you were thinking that seasoned writers never have writing jobs go bad, now you know. It happens to us all.

The contest: Tell us your worst writing job stories

Now that I’ve got you rolling, I want to hear your worst writing job stories. Here are the contest rules and prizes!

  • Post your worst client story here in the comments or on my Facebook page.
  • Only one entry per person.
  • Limit 200 words.
  • Contest ends: Monday (January 23, 2017) at midnight Eastern. I’ll come back and post the winner in the comments on Tuesday.

What can you win with your wretched tale of your most awful client ever? Here’s the lineup:

Grand prize: A 30-minute mentoring session with me and copies of ALL 9 of my currently available ebooks.

Runner up 1: A 30-minute coaching call with me plus all 4 Freelance Writers Den ebooks.

Runner up 2: A 30-minute coaching call.

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

UPDATE: The Winners!

I’m back to announce the winners of this contest. Thanks to all for some amazing stories, and great lessons in what NOT to do. 😉

Grand prize: Esther Copeland, for her horrifying tale of working 1.5 YEARS without pay and being stiffed to the tune of nearly $80,000.

Runner up: Samita Sarkar, who entered on my Facebook page, for her story of the client who turned into a stalker.

2nd Runner up: Lana, for her tale of the client that freaked out over how fast her great post was indexed on Google…and ended up winning a refund through her payment processor, despite all work being done to the client’s satisfaction.

P.S. If you’d like a lot better clients, you might want to check out the free training video featured below:




  1. Alvin leong

    People tend to think writing is a way to riches but only if you’re the next stephen king or jk rowling, most writers should just be happy to make a good living out of it.Just like the illiterate real estate developer who wanted someone to do his book, a well lettered man does not ensure a life of wealth and fame.

  2. Susie Rosse

    I don’t have a story since I’m new to freelancing but I have a question: Why don’t writers just ask for all of the money upfront? You can’t make a contract asking for 100% upfront? That doesn’t seem like a common strategy, but when you order almost anything online, you pay upfront, so why not do the same for virtual work?

    • Carol Tice

      Susie, many prospects won’t pay 100% upfront — because then all the risk is on them. 30-50% upfront is pretty standard, though.

    • Susie Rosse

      Hmm. That is a shame…

    • Carol Tice

      I do know writers who insist on 100% up front for first assignments with new clients, and sometimes, they get it. And they just pick the clients willing to go for that.

    • Susie Rosse

      That’s a great idea! Why only for the first project?

    • Carol Tice

      Well, because hopefully after that you’ve built up some trust. I usually just bill ongoing clients at the end of the month.

    • Susie Rosse

      Yes, it does sound great for building up trust, thanks!

  3. Ankit Raj Goyal

    I am an absolute newbie of a writer. Understandably , I got no stories of misery to share. What I do have is, of course, like any other newbie, butterflies, big ones, in my stomach at starting out .

    Here’s a playback of my worst nightmare . I am hoping it gets to enter the contest , maybe in a category of its own , something like Paranoid Projective NonFiction

    It was a time when my writing mojo was at an all time high.An year into writing, I believed I had learnt the ropes well enough for things to be getting really interesting . Though I was doing mostly flat pieces for local dailies and pamphlets, I was happy and expectant .

    Then I got this call. Warm Sunday morning in India, I was lazing around half expecting to sulk the day through when “The Call” came through.( As it turned out , it did have parallels with the more famous one that the Backstreet Boys had back in the 2000s).It was an offer for a film script, from one of the top production houses in Bollywood . No point even trying to say how I felt . Well , one thing led to another and very soon , I was penning away , burning the midnight oil , ready to “make it” , finally .

    I submitted the script (it was strange they kept me aloof from the rest of the team , but I was too high to complain ). It was a period drama, touching on some sensitive political issues. Well, I was all set , waiting for the theatrical release. What I did get was indeed a release, though not in a theatre, but in a tabloid . Turned out, they set me up to cover up for someone who had already published something highly objectionable. My script was to really get me into the game and make it real.

    I ended up being fined a sizeable share of my pre writing savings. So that was the worst I had.

  4. Melissa Cabral

    I used to work for a Content Mill that paid us $1 per 100 words. It was my first time ever doing freelance writing, so I was really excited about all our fun and geeky assignments.

    The main editor eventually approached me a few days later telling me I was doing a great job, that I was one of their best writers, and asked if I be interested in another one. I was psyched!

    And then he’d ask if I could add another project onto my plate… again… and again… and again… examples including:

    * An e-book where I had to interview people… without a raise.
    * 250 word news articles… 64 (!?) in total PER MONTH. At first he said EVERY. WEEK. (?!)
    * Could I pleaseeeee write 25k words in one night (!?)

    I started burning out so fast, I got sick! I eventually resigned for health reasons. But why didn’t I turn them down? My younger self thought I had to keep putting my best foot forward since there was always the promise of “better paying assignments” and bonuses… that never came. I had to chase them down for around a year to get my final pay.

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