30 Reasons You’re Failing at Becoming a Freelance Writer

Are any of these stopping you from becoming a freelance writer online? Be honest.

  1. You haven’t started a blog on your website because you think nobody will want to read it.
  2. You have no social media presence as you think building a healthy following will take forever.
  3. You don’t tell people you’re a writer; instead you tell them about the day job you hate.
  4. You haven’t pitched to guest blog on any popular blogs because you think they’re out of your league.
  5. You’ve failed to pitch to clients yet as you think they won’t respond to your emails or just outright reject you.
  6. You listen to everyone when they tell you that becoming a freelance writer as your full-time job is difficult/risky/just a pipe dream (delete where applicable).
  7. You can’t discipline yourself to work due to years of being conditioned to respond to being told what to do and when to do it.
  8. You think managing your own invoices, taxes and expenses is beyond a mind as creative as your own.
  9. You think when you should be doing.
  10. You live beyond your means: you buy more things you don’t need (nor truly want), keeping you trapped in a financial situation you assume you need a salaried job to pay for.
  11. You compare yourself to everyone else.
  12. You don’t take the time to read up on your new profession, to study your craft and strive to be better.
  13. You don’t read very much at all.
  14. You don’t write every day.
  15. You see writing as a chore now.
  16. Deep down you don’t really want to realise this dream of becoming a freelance writer, you just want a way out of your current situation.
  17. You’re not prepared to sacrifice a little to achieve a lot.
  18. You don’t charge enough for your writing because you don’t take yourself seriously as a writer yet.
  19. You don’t write down your goals – whether that’s daily to-do lists or bigger, grander plans.
  20. You don’t make your own rules as you’re so used to somebody else making them for you. As a result, you never consider there could be a different, perhaps unorthodox way to succeed.
  21. You don’t have supportive friends and family. (Although not essential, this one always helps.)
  22. You have no idea that becoming a freelance writer will take a lot of time and a good dose of effort, and you’re too impatient to keep working so hard when you can’t see what’s around the next corner.
  23. You have little faith in yourself – either personally, professionally or both.
  24. You refuse to step outside your comfort zone, no matter what the reward might be if you do.
  25. When you read about somebody else successfully becoming a freelance writer you assume it’s because they had special help/amazing confidence/skills you don’t have, etc.
  26. You’re not nurturing contacts – a tribe – to support you and cheer you on.
  27. You haven’t got an email list of potential readers and/or clients.
  28. You don’t look for other possible revenue streams to help you out while you’re building your new career.
  29. If you’re honest, becoming a freelance writer actually scares you; you secretly can’t live without the security of a steady, salaried job.
  30. You think you have to live your life like everyone else expects you to, instead of how you want to live it.

So there it is – 30 things that could be stopping you from becoming a freelance writer. If some sound slightly harsh, remember: I couldn’t know any of these without having experienced them myself.

PS: To get started as an online writer from scratch, you’ll need a few writing clips. I got you covered: find out how to build a writing portfolio in this FREE eBook.

Photo by Nathan Dumlao.

24 thoughts on “30 Reasons You’re Failing at Becoming a Freelance Writer

  1. Hi Kirsty — interesting post — some REALLY true points here, and others I wouldn’t agree with so much. Not every freelance writer really NEEDS to blog, so I’d never put that #1.

    But my real question is…where are the share buttons? I’m sure you’d get more readers if it were easy to retweet this… 😉

    1. Hi Carol, thanks for taking the time to comment. I’m glad you enjoyed the article, and regarding point number one perhaps I should clarify that I feel it is mainly the case that online freelance writers should start a blog. Either way writing a blog is good practice – for writing and discipline!

      I’ve been having a few problems with the share buttons at the moment – they’re on my main blog page if you scroll down but not on the individual posts! I’m getting this sorted right away so thanks – and thanks again for stopping by. I really appreciate it 🙂

  2. You have MANY good points here. Fortunately, I don’t think any of them apply to me, but that’s mainly because I’ve been blogging for over two years now (it will be three in May) and also because I’ve been doing a LOT of reading about freelance writing so I’ve already got the message about not charging enough, getting over the fear of putting myself out there, etc.

    I think #22 is the kicker. Most people do not have the drive and discipline to stick with pretty much anything outside their comfort zone, much less putting their thoughts and ideas out the in the big, wide, scary world. I’m a very persistent person (I have a son like this…when he was little he was just stubborn, but that stubbornness can be shaped into persistence, a very valuable trait.)

    I have plans and goals for my writing and in spite of many health and other personal issues, I continue to work towards those goals. What is the other option? Wasting the time I’ve been given on this earth? I’ve never been that kind of person.

    Again, I think you’ve made a very important point. If people aren’t willing to tough it out through disappointment, discouragement, rejection, or even plain old boredom, they’re not going to achieve their goal of being a freelance writer. The challenges and roadblocks are too great for someone without a certain amount of stubbornness (I mean, persistence!)

    1. Absolutely Anne! Like you say, what’s the alternative? The time is going to pass anyway so why not spend it working hard on what you want, focusing and not giving up when the going gets a bit tough? I can tell by your words and your tone that the only possible outcome for somebody like you is success so all the very best with everything and keep on being stubborn (I mean persistent!!).

  3. Hi Kirsty – happy 30th.

    I’ve been a professional writer for almost 20 years and I’d agree with your insightful list. Not that I do them all!

    I would add that it really helps if you have a specific area to write about that you focus on at first – preferably one that you know a lot about that isn’t either travel or restaurant / book / cinema reviews.

    And that you should make sure that your ideas are better than anyone else’s.

    1. Agreed. Wow, what a long career you’ve had already – I’m sure you’ve picked up lots of great tips and practices along the way. Thanks for commenting and thanks for the birthday wishes too!

  4. Hello Kirsty
    Just read your 30 tips. It really spoke to me (unfortunately) BUT … (the big but) I intend changing the negatives and thank you for the insight. I have just made the break from the safe, soft and often punishing (retrenched 4 times in six years)and am determined to be brave and do what I love doing – writing. I am slowly chipping away at it and am finding it is a longer process than I imagined. However, that said I’m taking small steps and achieving small goals fitfully. Thanks for your clarity and I know it will spur me on.

    1. Good to hear Raine! You’re so right about how it’s a longer process than anyone can imagine. Patience has never been my virtue but I’ve had to learn to acquire some… All the very best to you – keep at it: a little bit, often can go a long way.

  5. I absolutely LOVE #3 on this list. Not that they don’t all strike a chord, but this applies to about 90% of the wannabe freelance writers I talk to. Great list!

    (By the way, I’m stopping by after seeing your post in the LinkedIn group, Writeful Share.)

    1. Welcome from LinkedIn Emily! Thanks for stopping by. Number 3 on the list is so crucial because it’s to do with what you tell yourself about the direction you’re headed in and that’s so important. (You’re website looks fantastic by the way – looking forward to your blog so be sure to let me know when it’s up!)

  6. This list is very true! I’m new to freelance writing and I’m sure I’m guilty of at least half of these. But I plan to work to change as much as I can. Thank you!

    Forgive my question, but how can you tie an email list to freelance writing? I’ve always associated email lists with businesses and such.

    1. Hi Megan! Glad you found this useful. If you have a blog then it’s a great idea to start a small email list so you can stay directly in touch with your readers.

  7. Hi, Kirsty! Wow, a lot of those touch some nerves, eh? I know I personally have been striving to avoid a lot of them. I confess that #24 gets me. 😉

    Great post! I look forward to reading more from you!

  8. Great list! I didn’t make a total but way too many of these apply to me. I’m just about making it as a freelance writer but have a long way to go.

    Thanks for creating such a succinct list.

    PS – both check boxes below the comment form seem to be for the same thing, at least according to their text labels:

    Notify me of followup comments via e-mail.
    Notify me of follow-up comments by email.


  9. You know what I found super interesting about this list, Kirsty? Most of these reasons for failure have more to do with attitude than with aptitude.

    Some of the most talented writers have never put pen to paper simply because they lack faith they can do so successfully.

    Great post!



    1. You’re so right, Brent. This is exactly what I was hoping people would realise with this post.

      Thanks for stopping by!

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  11. This reason “You don’t write every day.” is one of the top… i think it should be on the first instead of 14th… because we don’t write every day we will forget writing… and yes… if i would put another reason that will be ” do read everyday” to become a good writer…

  12. חברת סינרגיה בעלת ניסיון|מתמחה|עוסקת|פועלת רב לא מבוטל במגוון תחומים שונים.
    השירות ניתן במגוון דירות דיסקרטיות איכותיות וחדרים
    לפי שעה בכל רחבי הארץ, אך ניתן להזמין אותו גם לבית הפרטי.
    מ – ייצור והתקנה של גדרות ורשתות לבית ולבתי עסק.
    סטליס רהיטים מתמחים בייצור רהיטים לבית ולגן תוך דגש על
    איכות הרהיט, מראהו ומחירו! עבודה מהבית היא לא
    בשביל כולם, יש לה יתרונות ויש לה חסרונות, אולם בדרך כלל היתרונות עולות על החסרונות של עבודה רגילה.
    כאשר מדובר בסוג עיסוי מפנק בנתניה/השרון מסוים יש לוודא כי זה העיסוי מפנק הנחוץ לכם.
    אם הגעתם ישר לקליניקה ברמת הגולן אשר בה הזמנתם
    עיסוי מפנק בתל אביב ישר מהעבודה,
    תהיה לכם אפשרות להתקלח בקליניקה
    ברמת הגולן ולהתחיל עם עיסוי מפנק ברמת הגולן תוכלו לבחור איזה או גבר
    שיבצעו עבורכם את העיסוי. לא משנה אם מדובר במאהבת או באישה שהתחתנתם איתה.
    שימו לב: אם לא מצאתם את מבוקשיכם בקטגוריה עיסוי
    בקריות, אתם מוזמנים לבדוק עוד אופציות עם שאר המטפלים שבאתר בקטגוריה עיסוי בצפון.

    חופשה חד פעמית בצפון ניתן למצוא באחוזת הכתר ששוכנת במושבת מגדל.
    צוות הפורטל דואג למיין את בעלי המקצוע לפי קטגוריות ראשיות
    ותתי קטגוריות בכדי שהחיפוש יהיה נוח

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