3 Tip-Offs That Your Dream Writing Job Will Really be a Nightmare


businessman with question maskRecently, I had an interview for what seemed like a dream writing job.

It was in a field I love. The work was right up my alley. And it couldn’t have come at a better time. I was in a slow period of assignments and getting concerned about cash flow.

After a successful meeting with a mid-level manager, I met with the head of the company.

It was ghastly.

Not only did she slash the hourly rate previously quoted to me, but she was rude. She also made several disparaging comments about my former profession. (I’m a licensed attorney.)

After I weighed the pros and cons of taking the gig, I decided it was a ‘no.’ It was scary to walk away from additional income, but my instincts told me it just wouldn’t be worth it.

Turns out, I made the right decision. A couple of weeks later, I landed a job through idealist.org with a legal nonprofit that needed a writer to blog, produce web content, and write grant proposals. After meeting with their very friendly director, I accepted a long-term, $3,000-a-month gig.

How can you tell if a writing job is a good fit, or has all the makings of a hair-pulling nightmare? Here are the three questions I ask:

1. Will the client be difficult?

If you see endless rounds of edits and client emails at 3 a.m. in your future, the time spent on the project will be longer, the work more draining, and the hourly rate lower.

Does the client have a reputation for taking forever to pay invoices? Make sure the rate you’re paid justifies the hassle, and that you’ll be paid promptly.

When I sat with that company head to discuss what I thought would be my dream job, she actually told me that I’d be incapable of editing her articles. After I heard that, her voice faded away for a moment, while a scene played out in my head of me spending countless hours going back and forth with her over a 500-word blog post.

Even if she’d offered me a really high pay rate, I’m not sure I would have taken the position.

2. Are you releasing the rights to your work?

If you sign away all your rights, you forfeit potential extra income from reprints or repurposing your work.

Read agreements carefully and know what rights you retain to your work.

If a company won’t budge on rights, you may be able to negotiate a higher rate of pay. Or you can walk away and look for a more writer-friendly gig.

3. Will the work enhance your portfolio?

My dream client wanted me to remain a secret, which would have prevented me from showcasing the work I did for her to attract future clients.

If a client requires you to sign a confidentiality agreement and won’t let you use the work you produce as part of your portfolio, you earn money but don’t get bragging rights or writing samples.

I considered these factors, which made it easy to walk away from the ‘dream’ project. Soon, another much better writing opportunity come along — which I wouldn’t have been able to take if I’d accepted the first project.

It can be tempting to take whatever paid work you are offered. But if it’s not a good fit, it’s probably not worth it.

What tips you off a prospect is a loser? Give us your tips in the comments.

Kristin Gallagher is a writer and attorney who lives in New York City.


  1. David Frank

    When I was young, my dream was to become an astronaut. Then I wanted to become a football player. Then I wanted to become a scientist. Then I wanted to become a DJ. Now I am a news reporter. Its amazing how the definition of “Dream Job” changes with time. What did you want to become when you were a kid Carol?

    • Carol Tice

      A songwriter, David…so my dream just sort of took a quarter-turn in another direction.

    • David Frank

      Well, on the plus side, it was only a quarter turn unlike my multiple u-turns 🙂

  2. Debbie Kane

    I fired a client who I realized was a mistake almost immediately after I started work for him. He emailed me at 1 a.m.; rewrote almost all my copy; told me what time I should post on social media; and, when I asked questions about assignments, would sarcastically ask “do you get it now?” Should’ve realized he was trouble when I saw in the contract language that said “Client agrees to treat Contractor professionally and with courtesy.”

    • Carol Tice

      So that was in the contract HE wrote, and then he still was an assclown? That’s kind of funny…like he’s *trying* to help himself behave professionally, but he still can’t.

  3. KaSonndra

    This just goes to show that it isn’t always about the money, or even the freedom gained from working a dream job. It’s also about making sure you’re doing the best thing for your mental well-being too. I’m so glad I stumbled onto your site. As I make the transition from full-time employee to work at home mom, I find myself feeling slightly confused and overwhelmed at times. I want to be sure I make the right decisions when going through this transition, and let me just tell you, it’s scary as sin. Your situation with this firm has given me the courage to make that first move and be strong enough to make sure it aligns with my needs. Thx for sharing.

  4. Philippa Willitts

    “I can’t pay you to write this book right now, but we could split the profits 50-50 when it’s launched”

    That would be an absolute, unequivocal no, then! I wouldn’t do that for a blog post, never mind an entire book!

    • Carol Tice

      Yeah, might as well go to Vegas and put it all on red — probably better odds that you’ll get paid than writing a book for someone on spec.

    • Philippa Willitts

      Especially when I’d never worked with (or heard of) him before, he didn’t have a website, and his entire marketing plan for the book was, “Uhhh, PPC ads, I think”.

      Nah. Vegas would be much more fun. I like your thinking 😉

  5. Amy Dunn Moscoso

    Hi Kristen,

    Great post. So often there are those early warning signs – and how clients treat others in coffee shops, at meetings and when they are not present says loads. Luckily, after a nightmare or two, I’ve started listening and life is oh so much better.

    I think your portfolio point is key-I feel like in freelancing, if it isn’t on your portfolio, then it didn’t happen, so incognito work had better be doing something else, like paying for a vacation, new car or a mortgage for three months, or leading to testimonials and recommendations.

    Thanks for this!


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