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.

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47 comments on “3 Tip-Offs That Your Dream Writing Job Will Really be a Nightmare
  1. Penny Hawes says:

    I can really relate to this post. In early February I landed what I thought was a dream job, writing newsletters and doing social media for a high end company in my niche.

    In the conference call and email communications I had before taking this job, everything seemed golden. I asked what they wanted, told them what I’d provide. We settled on a fee of $1800 per month, signed the contract, and the first check was direct deposited into my account. The whole time, while things seemed great on the surface, I had this deep irrational feeling of dread. It was weird, but I kept thinking “Be careful what you wish for”…

    Literally my first day of work, I started to get the feeling that I should have listened to my gut feeling…

    Suddenly the nice woman who was my contact became a complaining, stonewalling ogre. When I asked for information about the company, she sent me a rude email saying that they hired me to do the writing, she shouldn’t have to do it for me…. Answers to my emails were rude and unhelpful (when I could get any response) and I was seriously miserable.

    A month later, when the next check was due in my account, I received an email saying they were terminating the contract immediately. I could probably have hired a lawyer and fought, but at that point, all I wanted was to be done.

    This has actually been surprisingly hard for me to recover from emotionally, and I’ve changed my direction a little and have avoided sending LOIs to larger companies for fear of repeating the horrid experience.

    It was a relief when I had a conference call with a company for whom I’m blogging to discuss edits to a post I had submitted – they liked it and wanted me to break it down into a series because there was so much information to cover!

    Lessons learned? It may be trite, but sometimes when it seems too good to be true, it actually is. Also trite, but true – money isn’t everything… For me, being happy with my work and in my work situation is more important than one client that pays well.
    Penny Hawes recently posted…So Long, Farewell…. Quitting email subscriptionsMy Profile

  2. Sharon says:

    Thank you, Carol. When I did ask about competitors, the response was kind of broad: any tourism focused website concerned with my metropolitan area…and even the history channel. He said I could always check with him first. This was definitely an eye opening experience.

    • Carol Tice says:

      That is extremely constraining and vague. I strongly resist agreeing to anything like that. I’d challenge the legality of his prohibiting you from writing for a broad range of sites in your market for a year after you’re done with his work.

  3. Sharon says:

    Great article! I find this piece, and the comments, very helpful, though I wish I had seen this earlier. A few months ago I accepted what seemed like a great opportunity. Now I’ve learned to go with my gut. I had hoped to be a contributor to a history-themed sightseeing website, but several things diminished my initial enthusiasm.

    I would not have a byline, which didn’t bother me so much until I read the contract. I had to relinquish all rights. However, I was told I could still use the material for writing samples. There was also a random competition clause, stating I could not work for any competitors for up to a year after ceasing writing for this publication.

    Also troubling was that my first two articles were to be trial pieces – for half my quoted rate. I felt very conflicted. How could I turn down an opportunity to write about history for a popular audience and actually get paid for it? I also really wanted writing samples.

    I decided to go for it, even though my gut said no. I ended up unsatisfied with the first two stories I submitted, but was determined to meet the deadline. I had to wait several weeks for feedback. I soon realized this wasn’t going to work for either party and broke it off. I also realized I was not a right fit for the publication anyway.

    • Carol Tice says:

      Sharon, I consider that noncompete clause you got — no competitors for a year *after* you stop — very onerous. I’ve never agreed to that.

      If they try to do this, you want to make them name a few key competitors you won’t write for, or a geographic area — you want to limit who the competitors are.

      And the constraint should end within a short time of your stopping work for them, ideally the DAY you stop, but maybe 90 days is acceptable. It may even be technically illegal to forbid you to write for competitors when no longer in their employ — it’s restraint of trade, in my view. As a freelancer, they don’t own you and shouldn’t have the right to tell you who else you can work for.

  4. Steve Wagner says:

    When they answer some of my questions but not all of them, that’s a tip-off that they are either withholding something or they don’t quite pay enough attention.

  5. I turn down more assignments than I accept, I’m afraid. The most recent one (last week) offered $500 for research and writing of about 10,000 words over a one-month period.
    Sometimes, though, even if the “dream” job turns out to be a nightmare, there are benefits. I once got my “dream” job with a major daily newspaper, only to discover that I could not work in person with the editor who had been easy to work with as a freelancer. But during my tenure at the paper, I secured a weekly column assignment from a different department of the newspaper that lasted for another 11 years. And, strange to say, I went back to freelancing a lot for the editor I had trouble getting along with in person.

    • Carol Tice says:

      Well, if you’re offered a lot of ‘junk’ assignments like that, I’m glad you’re turning them down. You might want to look at how you’re qualifying clients to stop getting the lowballers — I also know people who put up a rate sheet with minimums on their writer site to help send those folks away and save time.

  6. David Frank says:

    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?

  7. Debbie Kane says:

    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.”
    Debbie Kane recently posted…Three Strategies for Managing the UnexpectedMy Profile

    • Carol Tice says:

      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.

  8. KaSonndra says:

    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.

  9. “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!
    Philippa Willitts recently posted…50 Free Online Writing CoursesMy Profile

  10. 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!


  11. Dave says:

    um: apologies for typos and grammatical mistakes! My phone-thumb needs to practice some restraint!

  12. Dave says:

    Inspiring post: it’s courageous and displays a confidence in yourself oin a healthy, good way. I’m still trying to develop this as being new to – not writing – but the field. I’m unemployed right now, which brings low confidence, along with me having a track record of saying “no” to things, mostly out of fear, it’s difficult for me to trust what my gut is telling me. Just a comment to say that trusting your gut is great advice. It’s just very hard to do so when self-confidence is low, and anxiety about income high. Thanks so much!

  13. Stacey says:

    I’m so glad you went with your gut on this! I’ve always found my gut to be the best indicator of when something’s wrong.

    I’ve had a few of the “I don’t know what I want” people as mentioned by a few commenters and had some really low offers – yes, even people who want free work. I’m rolling with the punches right now because I know I will find an awesome oportunity very soon, just like you did.

  14. Cherese Cobb says:


    I needed this post so much. I just had two very similar experiences. I was contacted via Linkedin about an opportunity to work for a mom and pop weight loss company. When I asked to see their website–crickets. As someone who has struggled with weight my whole life, I just wanted to make they weren’t selling magic bullets! Then I was contacted by a cabin rental company. The client told me that he wanted 500 word posts. When I told him I wanted to be paid…he stopped corresponding.

    I am happy you’re earning 3,000 per month at the idealist.com! I am sorry that a client would poke fun at your former profession–an attorney (Wow!). In my opinion, whether you worked as a Doctor or at McDonald’s, you still have something to add.

  15. JG Collins says:

    I’ve had to clean up manuscripts at two different companies by people who couldn’t write a coherent sentence. Every line in their m/s had to be converted into a logical statement before it could be rewritten. Bad grammar or spelling wasn’t a problem; I can deal with that. But I couldn’t even figure out what they intended to say.

  16. Gina Horkey says:

    I think that you also have to follow your gut. I had what I thought was my dream gig only to find out that the company was taking their marketing “in a different direction” mere weeks after their site, company and blog launched. They didn’t promote posts at all and were reluctant to move from the blogger platform…should’ve tipped me off right there;-) All’s well that end’s well. A $3k/m gig sounds pretty dreamy though!!
    Gina Horkey recently posted…The 10 Most Effective Time Management Tips from Top WebpreneursMy Profile

  17. I would consider the following to be red flags–not as common as some of those mentioned above, but they’ve all happened to me at one time or another.

    -The prospect wants you to do all the work “onsite.” Likely sign of a micromanager–and a future argument over who pays your commute expenses.

    -The prospect acts as if he’s doing you a favor by offering to hiring you–or, worse, acts like a paternalistic hand-holder working with a desperate charity case. My personal experience there was with a casual acquaintance of a casual acquaintance; apparently our mutual contact mentioned to the prospect that I was short of work, which was true, but I wasn’t exactly eager to build a long-term relationship with him after he came back several times to the comment “I could probably have found someone with more experience, but I know you really need the work.”

    -The prospect treats you like a therapist and unloads the full details of her life struggles on you at your first meeting. Happens most often with newbie aspiring authors who want you to ghostwrite their memoirs.

    -The prospect is a small business, or a single individual, who puts excessive emphasis on the importance of the “mission” behind the writing. Most everyone I ever heard of who did this, was secretly hoping that the writer would become so enthralled with the mission as to spontaneously decide to turn the work-for-hire into a volunteer project–and, when that didn’t happen, switched into “and I thought you were a good person, and couldn’t you see how limited my funds were?” whining mode.

    One thing that virtually every red flag mentioned here seems to have hiding just under the surface, is an attitude that “the only thing that REALLY matters is that *I* get maximum benefit from this.” It’s poetic justice that, being impossible to satisfy and incapable of building long-term relationships, they rarely get the MB.
    Katherine Swarts recently posted…Change Is a Journey, Not a DestinationMy Profile

  18. Sharyn Inzunza says:

    Hi Carol,

    Thank you for another great article. I am new to your website and appreciate the insight – the “way it really is” information – you share. I am new to professional writing and almost at the working-with-clients level. As someone who gives 100%, I am so glad to learn some insider tips before I find myself in a nightmare-client situation.

  19. Katherine says:

    Excellent post. When analyzing the nightmare projects I’ve taken on, they all had one thing in common – I ignored my gut instinct. Good for you for honoring yours! Your experience brings home the point that it is unnecessary to let in a bad situation. That just blocks us from finding jobs that are much better for our skills and personalities.
    Katherine recently posted…5 Ways to Earn Money FastMy Profile

  20. Leigh says:

    Back in my early freelancing days, I had a client hire me to write some sell sheets for an upcoming trade show. At one point in the project, I told him there was no product info available for XYZ product. He said, and I quote, “Use your divine powers of literary persuasion” to write something.

    This might shock you, but do you know that he never paid me for my work? I chased that $1,310 for months and then finally gave up. Turns out the guy was in the habit of hiring people and not paying them. One of his former employees was involved in a Dept. of Labor case against the guy, and a local printer was suing the guy for not paying for thousands of dollars worth of work.

    If they don’t know what they want, run.

    • Carol Tice says:

      Well, that’s another one of my red flags — clients who seem to imagine you can make things up about their products or services out of whole cloth, without talking to them, their managers, their customers, nobody. What?

    • Kristin says:

      Yikes! Sounds like a nightmare client for sure!

  21. Clients who don’t know what they want is now a mainstay in my field (eLearning). It started around the time of MOOCs emerging, and has evolved into chaos.

    I actually just left a gig that – at first glance – seemed to have its act together. However, like Kristen offers in her article, my need for gap work clouded my vision in seeing red (pink? – they weren’t so obvious…) flags. I am now building clips for a new venture: health and medical writing. Onward!

  22. Willi Morris says:

    This was right on time, thank you!

    Generally, I can get a vibe from people when I meet them, so if I feel like I couldn’t stand to have dinner with them, I don’t work with them.
    Willi Morris recently posted…How to Get Gutsy & Make the Big Ask to Influential PeopleMy Profile

    • Kristin says:

      Good point! I once walked away from a job at a law firm because the hiring attorney yelled at someone in the hallway. Having dinner with him (and working for him!) would have been a nightmare!

      • Oh wow, good call on that, Kristin. I believe there’s never a good reason to yell at another person (except if they’re on fire and don’t notice or something like that).

  23. Another one that doesn’t work for me-gang editing. When every project has to be “approved by the X committee”, I know it isn’t going to go well.

  24. Nancy Ketchman says:

    Great post. Several years ago I accepted a marketing/writing assignment (brochures, sell sheets) for a design/construction firm in which bright, flashing warning signs were going off in my head during our initial meeting. I ignored them and paid the price. They were:

    1. The two company owners disagreed with each other on what they wanted and what style they liked. I thought I could navigate this, but their continual disagreement dogged me throughout the project, resulting in constant rewrites. If one was happy, the other wasn’t.
    2. The owners told me that they had gone through several marketing writers before and hopefully “I would get it.” I should have ran out the door then. Not working out with one writer is OK, but several?
    3. One of the owners said their business is hard to explain. Really? Design/construction? I have a background in healthcare maintenance and environmental science. I don’t think so.

    After six painful months – coming home and breaking into tears, thinking, “Am I really this incompetent?”- I finally worked up the nerve to “break-up with them,” telling them it’s clear this arrangement isn’t working out. Both of us were relieved. But my one other mistake – and I’ll never do it again – was initially trying to work it out by reducing my invoice as a “good faith gesture” to preserve the business. It didn’t work anyway and I was out nearly $1,000.

    I recommended a highly regarded marketing firm, who took on this client after I left. They also “separated” after several months and I heard through the grapevine that this other marketing firm experienced the same problems.

    It wasn’t me after all. Always trust your gut!

    • Carol Tice says:

      Thanks for sharing this great story, Nancy. I wish more writers would realize that so often, it *isn’t* about you.

      I see many book-ghosting offers that indicate they’ve already tried and failed with another writer…and I tend to not apply for those. 😉

    • Kristin says:

      Thanks for your comment! Hindsight is 20/20, as they say! Glad you had the courage to “break up” with a bad client!

  25. Ken says:

    Poor grammar, no clear vision or idea of what he wants, people who claim they are ‘startups’, “there will be more work if you do well.”, people who think “it’s quick and easy”, people who expect things to be turned around in hours instead of days (or even weeks), people who haggle, haggle, haggle.