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. 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.

  2. 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.

  3. 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.

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