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

Carol Tice

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. Jason

    The biggest obstacle I always occur is just stopping to write and taking breaks, I`m always having biggest issue to resume from a break into writing, and it pretty much delays my entire work, therefor I have decided to stop taking any break while writing and really just write and finish, and only then I allow myself to take break.

  2. Anna

    My biggest obstacle is having from time to time too long brakes. After that it is so hard to start and focus again..:(

  3. Josh Sarz

    Fear is definitely one of the biggest problems when you’re still starting.

  4. Debra Stang

    I think my biggest problem is negotiating. I’m still amazed that people will actually pay me to do something I love so much that it’s easy for me to forget I’m in business and just grab the first offer.

    • Carol Tice

      Really common issue — which is why #3 ranks so high on our list!

  5. Matthew

    Focusing on one market is very good advice, especially when starting out.

  6. Cindy

    I totally agree, fear is the biggest problem of the freelance writers. By the way, I found your webinar genial, I’m sure it will help many blogger and writers to upgrade their skills. Very nice article, thanks for sharing it!

    • Carol Tice

      Glad you liked the Webinar! That came out of a conversation Linda and I were having over winter break — we decided to record it on Skype, then we added slides…it just sort of kept growing until it was a full-blown presentation.

  7. Jude

    My biggest error is not consulting with experts before I launched my writing career online.

    • Carol Tice

      Aha — mentoring is actually one of the other points on our list. Talking to a pro who’s already doing it can really cut down your ramp time.

  8. Mummy Big Bum

    I am so sorry that this is my only comment – I’m up late, as ever – but just wanted to point out that in your second sentence you write ‘one one’! I know we all do it; I certainly do; but thought you might want to correct your typing error as this site is about giving advice to writers!

    • Carol Tice

      Ugh — thanks for catching that — off to fix.

  9. Miguel Leiva-Gomez

    My biggest obstacle was my location (Târgovişte, Romania), but I overcame that with Magic Jack. I can now have a US number and call any other US number for $19.95 a year. It’s awesome, and it helps me maintain a business-like aspect to writing.

    Now, my biggest obstacle is with achieving proper connections, referrals, and knowing the proper marketing venues that I should expose myself to. That’s also almost gone.

    Just to chime in, I’d like to say that fear constitutes a lack of confidence. No one is going to hire someone who doesn’t have confidence in her/himself. It’s all about believing in who you are and what you do before approaching the big-wigs. Have you ever seen a boss that is all timid and afraid of approaching people? Nah! Mostly, I see bosses with an inflated ego. Well, that’s what everyone needs to have in order to take off with freelance writing or any business!

  10. Amandah

    My biggest obstacle is determining if a client is legitimate or not. For example, I receive inquiries for my freelance writing services, I respond, and never hear from the ‘potential’ client. Perhaps, I scare them off with my per word rate (if they ask) or the fact that I ask for more information in order to prepare a quote. I do my best to screen a client by looking at their website, Googling their company, etc. I don’t know. It’s a conundrum!

    • Carol Tice

      There are a lot of flakes out there. I basically run on the assumption that it’s not a real gig until we have a signed contract and their check clears.

      I always respond that I’ll need a lot of info to prepare an accurate quote. That only scares off the scam artists. Real companies want you to know all about their project.

      I think the real problem is getting too excited with every nibble…I try to wait until I know it’s an actual gig I want to do.

  11. 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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