Do You Sabotage Your Freelance Writing Jobs? A Gut-Check

Carol Tice

Do you sabotage your freelance writing jobs? Makealivingwriting.comAre you one of those freelance writers who can’t seem to win no matter how hard you try? All the freelance writing jobs you touch seem to turn to merde. Things may start out well, but then something often goes wrong.

You don’t get paid. Your client drops you. All your prospects just want to know how little you’d be willing to do a gig for. And you’re always struggling to book more freelance writing jobs.

If this is you, listen up.

I’m going to tell you exactly why that’s happening, and how to fix it.

How do I know what’s up? I recently added a free, 1-on-1 consulting perk for all Freelance Writers Den members who’ve been in the Den a year or more. That turned out to be…500 writers!

So I’ve been talking with many, many writers who’ve been working on their careers a long time, and learning what keeps them broke, and why it’s so hard for many to find and keep freelance writing jobs that pay well.

Turns out, it’s mostly themselves. Let me spotlight the major mindset problems that lead you to choose crummy clients — or screw up better gigs — over and over. See if you recognize yourself in any of these archetypes of the low-paid freelancer:

The insanity trap

Time after time, I talk to writers who get all their freelance writing jobs off Craigslist or other mass job boards or bidding platforms. Their clients pay poorly.

But when I suggest that perhaps they should do proactive marketing and stop competing against 1,000 other writers for every gig in a race to the bottom on price, I get disbelief.

“But…I need to keep skimming those. I might miss something good!”

You probably won’t, because functional companies don’t place an ad and look through 800 resumes to find a writer. Right?

Doing the same marketing for freelance writing jobs that got you crummy clients, over and over again, means you are fulfilling Einstein’s definition of insanity — you’re doing the same thing repeatedly, but expecting a different result.

Online chat boards teem with writers who love to complain about how awful those lowball Craigslist ads are…but still, every week, those writers check those ads again. That’s self-defeating.

The fix: Change your marketing. Swim in a better pool, and you’ll find better clients, not just freelance writing jobs. Stop repeating what you’ve always done if you want to get paid — and treated — better.

Glass half-empty thinking

No matter how many good things happen to freelance writers, many can’t seem to look on the bright side. Instead of celebrating the wins, it’s all gloomy Eeyore attitude.

If a writer discovers a new marketing technique, or learns how to write a better query and gets a fat assignment, instead of patting themselves on the back for improving their business, I hear this:

“OK, really embarrassed that I didn’t know that! I can’t believe how stupid I was. Going to try to pick myself up off the floor now and move forward somehow…”

Some writers are driven to take a dim view of their abilities. Beating ourselves up about our shortcomings takes so much time, we don’t have time to build our careers or get the writing done!

Maybe you have:

  • Tons of clips — but they’re ‘too old’ (even though there’s no such thing)
  • Lots of experience — but think it’s not the right kind (as if our skills aren’t transferable)
  • Bombed on one client project — and instead of seeing that as a fluke, you decide you’re not a good writer

Instead of building confidence and giving yourself credit for your progress, you’re stuck in a look-on-the-bleak-side mentality. Whatever assets you have, you rush to downplay or dismiss their value.

The fix: Start counting your blessings. Each week, start by reviewing good things that happened in your career and your life in the past week. Keep a daily gratitude list, or a list of your strengths. Eliminate negative self-talk and actively replace it with positive affirmations.

Realize that successful freelance writers exude confidence. Start working on that. You can train yourself into a more positive mindset.

Taking half measures

Are you serious about making freelance writing your career? Or are you doing freelance writing jobs a little on the side, year after year, while complaining how you wish you could quit.

But it never seems to be the ‘right’ time.

So you do a little marketing, but not much. You don’t aim too high, staying away from the big companies or magazines that would pay well. You worry you wouldn’t be able to juggle the responsibility of more writing gigs, instead of rising to the challenge and pushing yourself to test your limits.

Anything you do halfway tends to get poor results. It takes a big commitment to launching your startup freelance business to really get the wheels spinning.

The fix: Get serious. Worry less about whether you can handle it, and more about being stuck in a day job you hate — or stuck with low-paying freelance writing jobs — for the rest of your life. Take it up a notch or three.

If you’ve been wanting to move into freelancing for years, consider tightening your belt, saving up a little money, trusting in your abilities, and simply quitting…right now. You can always go back to working a job later, if it really doesn’t work out.

Addicted to drama

Do you spend hours venting to your friends about your dysfunctional clients? It can be fun, recounting all the crazy demands they make, and you can get lots of sympathy for how awful they treated you.

But…if it’s a year later, and you’re still spending much of your free time complaining about your crummy clients or freelance writing jobs gone awry, something’s wrong.

You may have a weird fascination with these sorts of people, where in a way, you’re actually attracted to dysfunctional clients. Their scenario — the chaos and confusion, the last-minute demands — may feel familiar to you from your family growing up. Or maybe your life is boring and this provides some excitement.

In the short term, you may enjoy the schadenfreude of watching someone else’s trainwreck and thinking, “I’m glad I’m not like that!” But in fact, those trainwrecks are taking your career over a cliff, too.

The fix: Break the pattern. Realize you’re attracting people with poor business skills and are too willing to hop on their rickety bandwagon. Look at what your writer website and LinkedIn are telling people, and consider changing your messaging.

Before you sign up for a gig, ask yourself, “Are there red flags here?” Start setting healthy boundaries for what you’ll do, at what rate, by when.

The timid writer’s lament

When you don’t advocate for your freelance writing business, it doesn’t turn into a lucrative career. No one else is going to care how much you earn, or what you get to write about.

Insecure writers often:

  • Work for a client for years without ever asking for a raise
  • Ask few questions at first client meetings — then, cry when the client hates their draft
  • Work without a contract, if one isn’t offered
  • Start working for business clients without a deposit
  • Have clients who want 24/7 access or rush work at low rates

Again, writers…self-esteem is the culprit here. You have to believe you bring value to the table, or you don’t ask for the working conditions and pay you deserve.

The fix: Analyze how you do business. Then, make some changes. You need to speak up for what you deserve, even if it feels uncomfortable at first. Fake that ’til it starts to feel right. You’ll be pleasantly surprised by how many positive responses you get, and how much better your client relationships turn out.

A meditation for moving up

Ready to change your attitude and get better clients? Here’s something to tack on your wall:

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Get better freelance writing jobs

If some of those writer types I describe above felt familiar, it’s time for change. How can you stop sabotaging your freelance writing career?

List the behaviors or mindset problems you want to work on. Maybe, start with just one! Then, start a checklist of proactive steps you plan to take to change your mindset and your actions.

Keep building up your self-esteem and celebrating your wins. You can change the self-defeating behaviors that are sabotaging your freelance writing jobs.

Do you sabotage your writing jobs? Tell us what’s happening in the comments.

Get a free e-book (100+ Freelance Writing Questions Answered by Carol Tice) and free updates! Sign me up!


  1. Naomi T.

    Thanks for another swift kick, Carol. I’m still paying tuition in the school of life. Love that! Now on to meditating to move on up . . . with purpose.

  2. Lynda Dell

    Hello Carol,
    Your website is such a good resource! Here is a question that you don’t get very often: Is there a way to work part time writing and full time in a day job without investing a lot of time and money?

    I need to earn extra money to make up for our shortfall.Your boot camp courses on perfecting pitches are amazing, but I don’t have the budget or time for that now. Is there something on a smaller scale for a writer like me?

    I currently write feature articles for magazines and websites and recently started my Dare to Dream blog for dreamers, dream seekers, and dream makers, for women who are pursuing and realizing their dreams. I would like to branch out to national publications and major websites and to get affiliates for my blog, too–at some point.

    Are there baby steps that I could begin with right away that wouldn’t require a big commitment or cost? Are there five tips to write sensational queries?

    • Carol Tice

      Lynda, I think you’re confused about the time/money equation in launching a business.

      The equation is that you can EITHER invest tons and tons of time, learning everything yourself by trial and error…or you can pay for a shortcut such as one of my courses. For instance, there’s a useful one on sale right at this moment for a big $29, right here: It’s cheap and self-study — maybe a fit?

      You can take that and learn how to do marketing that gets you great gigs, how to do your writer site right, and lots of other stuff, for a pittance. Or you can take a year or four figuring it out yourself.

      OR…you could grab one of my Small Blog Big Income ebooks for a big $9, to work on building your blog into a money-earner (hint: If you just launched, it’s not time to get affiliates yet, you need to build your audience first):

      But something that takes no money OR time that skyrockets your writing income? Sorry, not that I’m aware.

      I think this is a useful post for you to read at this juncture, as it’s possible you may be a victim of a persistent myth about freelance writing, that’s it’s a quick and easy way to make money without investing anything in your business:

      One other thing you might do is read Linda Formichelli’s “Write Your Way Out of the Rat Race,” which is good for helping you juggle a FT job and a transition into freelancing.

      Are there baby steps? Sure. Loads of ’em, depending on your situation, willingness to do various types of marketing, personality, experience, etc. Can you figure out which are the right baby steps for you, that aren’t a waste of time based on where you’re at right now, without any advice, training, or coaching? Maybe, maybe not.

      For query tips…you can look at my query related posts on this tag, far more than 5 tips in here:

      Hope that helps!

  3. Peggy Diaco

    I haven’t started freelance writing yet, but I am investigating the business for my senior thesis. I’m a senior citizen going to college for a writing degree to supplement my income when I do retire (and to keep those brain cells active). Your article is very helpful for my “pitfalls” section. Your blogs and everyone’s comments are so helpful to me and I cannot wait to get started. Thank you.

  4. Karen Ingle

    Celebrating my wins will be my new habit. I’m keeping a file of kudos and successes. This is more than just fodder for testimonials on my website. This is a growing pile of treasure: reminders that I am a real writer, a good writer.

    • Carol Tice

      Karen, when I was a staffer, I used to save every complimentary letter to the editor that came in on my work, every piece of praise, every award certificate…and when I was feeling hopeless or in over my head on an article, I’d read through that file.

      Everyone should have one!

  5. Helen McCrone

    Thank you for this, and especially for A Meditation to Moving Up. So timely for me. Trying to deal with a new online marketing agency that’s abusing my good nature.

    I’ve started drawing lines in the sand, and my next step is to spell out exactly what I will and won’t do (for the benefit of both parties). I’ve already notified them I’m upping my rates for future projects. I’m going to read your motivation every day so I don’t weaken!

    One new thing I did this week was to write up an evaluation of each stage of the project (negotiation, quotation, briefing, production, timing, etc) and send it to the agency. At the end I added ‘lessons learned’ for me and for the agency so that we don’t repeat our mistakes. I’m hoping a little time spent evaluating a project fully and objectively will make the next project go more smoothly (and be paid appropriately!).

    • Carol Tice

      Well, if telling that agency how to do their business works out, I think that’ll be a first. 😉 Hope it does! Usually, I’d keep that kind of info for my OWN future learning.

    • Helen McCrone

      Well, it’s not the usual agency/writer scenario, Carol. This is someone I’ve worked with before and he’s setting up a new agency. It’s in Holland, where English copywriters who speak Dutch and have content marketing/SEO knowledge are very thin on the ground, so working with me actually brings him business.

      Trouble is, he pumps me for a lot of business advice, gets me to do all the work (like detailed quotations), and then takes a huge cut without offering to pay for my help. This has even been noticed by his clients, who’ve asked to work with me directly because ‘he does nothing’ (I’ve declined at this point for ethical reasons).

      I’m almost at the stage of walking away, but I don’t want to cut off my nose to spoil my face. So I thought an evaluation would be a good learning tool for both of us (he was actually grateful for it). Mind you, I also need to define in writing the boundaries of what I will and won’t do for him in future. Make it clear to both of us! 🙂

    • Carol Tice

      Helen…when they ask you to do more work, you send them a change order or additional work order that states what you’d do it for. Stop working for free! I get that it’s a good relationship…but perhaps it’s partly such a great setup and he loves it…because he’s exploiting you. This might be a useful read:

    • Helen McCrone

      Great article about misplaced loyalty, Carol. It’s me to a tee. I’ve printed it out and put it with your meditation for moving up so I won’t forget it.

      I like the idea of a change or additional work order. Formalizes it and avoids a surprise or difficult conversation at the end (if the order isn’t signed, I won’t do the additional work). I’m going to set up a template right now!

      Thanks so much for your advice. I’ve been feeling pretty low this last week, but Writer’s Den has once again come to the rescue! 🙂

    • Carol Tice

      Um… you work and then talk about money at the end? Don’t work without a signed approval of what they will pay!

      If you need forms, my Freelance Business Bootcamp ebook (see the ebooks tab above) has sample contracts and I know it’s got a change order, my co-author Neil Tortorella was big on that.

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