The 10 Biggest Obstacles to Freelance Writing Success (and how to solve them)

Carol Tice

obstacles to launching a freelance career

Are you having trouble getting your freelance writing career off the ground?

On one of my weekly podcasts recently, I was shocked to hear how many writers said they’d been trying to get their writing career going for a long time.

More than one had been trying for 10 years.

That’s bad! People need to eat.

And writers need to be able to earn a living with their work.

My personal New Year’s resolution is to help more writers begin to take action and become successful freelance writers in 2012.

Linda Formichelli and I got together to talk about it on Skype the other day. From that conversation, we put together this half-hour Webinar. It’s free to watch. Just a little New Year’s gift to my readers.

In it, we discuss the 10 most common obstacles to freelance writing success, and how to solve them.

What’s on our list? Here’s the top three:

  1. Fear. This is always at the top of the charts. You’re afraid you’ll be laughed at, you won’t be good enough, you’ll screw up, or that the economy is just too tough out there.
    Solution: To overcome your fear, try to experience it. Arrange for friends to laugh at one of your articles. You’ll see you survive — and that really, that’s probably not going to happen.
  2. Overwhelm. There are so many possible markets to pitch, and so many ways to do marketing. It’s easy to get boggled and do nothing.
    Solution: Stop trying to find the one best way to pursue freelance writing, and start getting out there. Break down your goals into small steps, and begin to take action. Choose one direction — one type of marketing, or one writing specialty — and focus in on only that.
  3. You don’t treat it like a business. Are you writing without a contract? Do you take the first price a prospective client offers you, instead of negotiating? If a client is late paying, do you just wait around for them to cut you a check? Stop being taken advantage of and take a businesslike attitude.
    Solution: Imagine you have a small retail shop, instead of a freelance-writing business. How would you run it? Do those business basics — negotiate, have a contract, collect what you’re owed, keep good records, and above all, consistently market your business.

For the other seven of our tips on overcoming the top freelance obstacles, head over to this page to register and watch the video — then, grab our free handout with all our tips. Linda and I share a lot of personal stories about the obstacles we faced starting out in our own writing careers, and how we overcame them.

What’s your biggest obstacle to freelance writing success? Leave a comment and tell me about it.


  1. Ali

    Hi Carol,

    I agree with Anna… I’ve just returned from a two-week break and I’m so rusty. I’m scared of writing a post on my blog, I’m hesitating when pitching a client and I’m scared of going on a break next time 🙁

    • Ali

      Thanks for the nice note, that’s highly encouraging 🙂

    • Liz

      Thank you for this tips, Fear is one of the greatest problem.

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