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

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:

Download (PDF, 4.93MB)

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.

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