23 Ways to Destroy Your Freelance Writing Career Before You Begin

Carol Tice

By Uttoran Sen

The U.S. Small Business Administration says that half of all new businesses fail in the first five years.

Freelance businesses can fall apart even faster without careful planning, because there are no bank loans or investors to back you up – it’s just you and your business.

Are you going to make your business a true success? Or kill it before it gets off the ground?

To be successful, you’ll be off to a good start if you can skip these business-killing moves.

1. Sell yourself short

There are plenty of easy writing jobs that pay pennies. If you’re content with making half of minimum wage, there’s no reason for you not to snatch up as many of these cheap writing jobs as you can find.

2. Forgo the business plan

If you were going to start a big business with millions of dollars from investors, you’d have a plan. But don’t bother having one – it’s only all of your own hard-earned money at stake.

3. Pander to clients

You’re a freelancer – that’s just another glorified term for cubicle jockey, right? Suck up to the clients – once they know you have no confidence, they’ll pay you squat.

4. Put your eggs in one basket

If you’re looking for almost immediate failure, go ahead and put all of your proverbial eggs in one basket. Then, when the client disappears without bothering to pay, you’ll be dead in the water.

5. Stop selling yourself

Once you have the first clients, why bother getting more? These first few will surely pay your bills forever. Besides, good marketing never really pays off.

6. Make a nasty name for yourself

Hey – you’re a freelancer, now. You’re wearing your big kid pants and the whole world should bow down and respect you. So treat everyone else like jerks.

7. Beg, borrow and steal

Only don’t bother with the borrowing. Just beg other writers for help all of the time until you drive them nuts.

Then steal concepts, articles, and ideas from their websites. That’ll really build your network.

8. Blow your deadlines

Big party tonight? Maybe Pinterest called to you for four hours straight?

Forget those deadlines and projects – just take the money and run. Surely the client saw that coming.

9. Ignore your real earning potential

It’s much easier to find bad-paying gigs that take advantage of good writers. So don’t bother exerting yourself – just take the cheap gigs and then complain endlessly about how nobody pays you enough.

10. Let others be the boss

Not sure how much to charge a client? Just take whatever the client offers.

Isn’t that easier than making your own decisions?

11. Write like a child

So you wrote a paper in the third grade that won a big smiley sticker? Great!

Clients pay a lot of money for people who keep writing just like that. Spell-check be damned.

12. Be ignorant

Nothing is more career-killing than pure ignorance. Maybe you should slander others online. Or perhaps call potential clients racist names.

They’ll think it was a funny joke, too.

13. Ignore sick days

You never get sick, right? The kids will always be healthy, too.

Schedule work for every free moment – you’ll never need a sick day.

14. Give the IRS nothing

Hey — this is your hard-earned money. You don’t own the government a dime! (Just tell the IRS that when they ask.)

15. Run a scam

Suck them in, spit them out. Who needs repeat business anyhow?

16. Pretend to be an expert

“Fake it ‘til you make it” is sound advice for those looking to sound professional. Pretend you’re a retired surgeon looking for extra income in the medical writing field, for instance.

17. Spread yourself thin

It’s important to be everyone at once if you’re really trying to fail quickly. Be sure to stay up 24 hours a day, wear yourself to the bone and not do anything very well.

18. Never learn anything new

Knowledge? We don’t need no stinkin’ knowledge. Obviously your way is the best way – others just need to wise up.

19. Get defensive

So your client dared ask for revisions on your written perfection? Why don’t you tell him to stick those revision requests where the sun don’t shine?

20. Start a corrupt business

Who doesn’t love a good content mill? They pay you $5. You pay him $1.

He eats caterpillars for a living and writes in crayon. Great plan!

21. Pick fights

Online fights are fun. Come out swinging on everything – especially issues you know very little about.

22. Complain to clients

Clients are like friends – you can tell them anything. They like to listen to you complain about your terrible life, your drug addiction, and your hate of people who undermine your pricing. That’ll keep them coming back for more.

23. Make excuses

Things not going your way? Why not crawl in bed with a box of tissues and a barrel full of excuses.


All sarcasm aside, freelance writing is an outstanding career if you’re willing to invest time, energy and resources in building the sort of career that you can be proud of.

It takes time, patience and diligence, but with careful handling you’ll avoid the pitfalls of freelance work and enjoy a thriving new business.

What freelance pitfalls have you fallen into? Leave a comment and add to this list.

Uttoran Sen has been a freelance writer since 2004. He likes to travel around the world and write about it on his travel blog. Connect with him on Twitter.


  1. Marisa

    I would have appreciated this post a lot more without the facetious tone. If the writer was also a comedian, I might have taken it all with a grain of salt. But, as it is, the snark is kind of annoying. Sorry.

    • Carol Tice

      Hi Marisa —

      Uttoran is unfortunately sidelined with an illness…but he promises he’ll be in to respond to comments in a few days.

      Personally, I loved the departure from my usual straightforward tone that he brought to this piece, so I was happy to have it.

      • Ed Estlow

        Gotta agree with Marisa, pretty much to the letter. Half the time I was confused with what he was trying to say.

      • Uttoran Sen

        hi Carol,
        Am back, somewhat.

        Will go through the rest of the comments and will respond to each and every one of them soon,

        Uttoran Sen,

    • Jane

      I have to agree with a previous poster’s comments that the advice would be much more welcome without the facetious/’snark’-y tone.

      As for me, the only pitfalls I have occasionally fallen into are dealing with short-changing clients (although I usually quote NUJ rates, my experience with some of them is that if you ask too much, you just won’t get the work) and occasionally feeling like crawling under my pillow when things aren’t booming — but in case you haven’t heard, there is a recession, and journalists are also dealing with many print operations shutting down to go digital, and in the process both deleting staff and shaving freelancers from their operations, so it is certainly a highly competitive market.

      One thing I could usefully do with knowing more about, however, is whether taking the time, energy and resources to set up and contribute regularly to a blog is really going to ensure my client base will soar — any non-snarky/facetious advice on that would be truly welcome.

      • Carol Tice

        Stay tuned next week for a whole series of posts on how to make your blog succeed, Jane!

        Also, Freelance Writers Den has a 4-hour bootcamp in it called How to Be a Well-Paid Blogger, all about how to leverage your own blog and set it up so that it gets you clients. We’re open through tomorrow if you want to check that out…

    • Uttoran Sen

      hi Marisa,
      thanks for your comment,

      Before sending this article to Carol, I had got it reviewed by my team of critics and the response was pretty much the same that I find in this comments section. Actually, this article was going to be very straight foreword and boring.

      It was something like:
      – Don’t Sell Yourself Short
      – Don’t Forget a Business Plan
      – Don’t Become an Employee
      – Never Put Your Eggs in One Basket

      Then Carol suggested: – If it’s 23 ways to destroy…shouldn’t the heads be like “Sell Yourself Short” and “Forget a Business Plan”?

      So I changed my tone along with the heads. My critics told me that if I went ahead with this, then some people will take it as an insult and will be very angry, so be prepared for some strong comments. Honestly, they told me that it will back fire, and I guess they were right.

      I guess Carol did not wanted this tone, perhaps she was looking for more sarcasm and fun, I too was trying for more fun, but it came out to be like this.

      I read the article again and I can’t disagree with myself that this article is different, much different that the thousands of other articles I have written. I could not stop myself from sending this article to Carol for publishing.

      All criticism accepted, just could not resist this version from getting published,

      P.S. – I would like to add this. Most people here are writers, that is, they have not hired writers themselves… they have just written for others. So, I guess your view is one dimensional. Someone like me who runs an online business which covers more than one niche and some of those niches are covered by other writers whom I hire… have allowed me to see this online freelance writing business from an angle that a writer might not be able to see.

      These things have happened… I always try out new writers for fresh content and ideas, but it also makes me a victim of some of these points. It will all seem pretty bad to you as a writer, but as an employer I have to deal with these.
      – “Fake it ‘til you make it”
      – So your client dared ask for revisions on your written perfection?
      – Beg, borrow and steal

      Uttoran Sen,

      • Carol Tice

        Hi Uttoran —

        Glad to see you’re back and feeling better!

        I liked the contrarian tone of this — and you’ll notice that the controversy around the approach meant it got a lot of attention, comments, and sharing.

        I think it’s important to push the envelope sometimes and write something that’s a bit provoking, and in my view seems like it got the desired result!

        I probably wouldn’t want to take this tone every day, but I think it was a nice change of pace around here. And definitely got people talking.

        • Linda Hamilton

          Actually reading this again now I shook my head and laughed at the tone and the sarcasm. I think it’s great! The last reason, Make Excuses, I found hysterical. Sure, you want to be a writer, but you’re finding it’s harder work than expected and now you have a pity party. I hear it all the time.

          This is a great piece for someone who understands the reality behind freelance writing and the hard work and focus that’s required to make it work. I wouldn’t read this tone every day, but for this piece it’s a great change and makes good points.

          If it’s sparked emotions, perhaps it hit a nerve with people who are guilty of some of these excuses but don’t want to admit it? I know I’m guilty of a couple but this piece strengthens my resolve for change. Just sayin’.

  2. Steve

    Hi, Uttoran!

    Great post, well-written and so to the point.

    I’ve got to admit that I’ve committed some of these “freelance felonies” from time to time!

    The “reverse logic” of the article was quite effective and really hit home. We often hear what we are supposed to do to become successful that we forget the things we do that are counter-productive.

    Again, thanks for the great article. Much needed and appreciated.
    Steve Maurer
    Maurer Copywriting.

  3. stacey

    Can I add one ? ” Show up with your shabby website, istock photos. and stolen samples…then get all ‘salty’ when the client you pitched says ” sorry, but we don’t think you’re a good fit for our business”.

    Whilst this ‘reverse logic’ post may seam a little snarky… I don’t think it’s designed to offend…but rather get you to up your game, and to be honest, it’s welcome change from the list posts that keep most blogs in business!

    I’ve committed a few of these myself, and any freelancer who says they haven’t either has no clients…or is lying.

  4. Laura Spencer

    Uttoran Sen,

    Sorry you’re feeling sick.

    I think this post was very effective. Sometimes a humorous post can make a point where the message of a non-humorous post would have been ignored.

  5. Thomas

    After reading this article, I couldn’t help but think. ‘There’s five minutes of my life I’ll never get back.’

    C’mon Carol, you can find better writers than this to guest post. This article reeked of those pathetic muses on Yahoo.

    • Carol Tice

      Boy, seems like readers are really split on the sarcrastic tone of this post! You either love it or hate it.

      Sorry you found it a disappointment, Thomas. I like to offer a variety of different points of view with my guest posts…seems like some people were rubbed the wrong way by the attitude here, which I find funny because I had a similar “how not to succeed” guest post a while back everybody loved.

      • Anita

        Perhaps it wasn’t the tone but the thin content of the post that prompted the comment. Most of the material you provide on your blog has more depth to it.

        • Carol Tice

          Well, this post has turned into a referendum on how individualized our senses of humor are. I found it amusing and a breezy read, but obviously not everyone did. I liked it precisely because it takes a very different approach than most of my posts. Trying to spice it up a little — but clearly this writer’s style was a little too spicy for quite a few readers.

  6. Linda H

    Have to admit I’m guilty of a couple of these.

    One that makes me laugh is #2. I’d written two business plans for the business, but when it came time to actually start it up I got so excited I neglected to review it. Once I did, things went a lot smoother.

    The other that made me laugh was #9. Can’t tell you how many times I’ve been called a ‘liar’ when I tell someone how much I can make on a gig. Then I give information and hear #23 and just move on.

    Like the sarcasm… it fits. Great post… makes you stop and think about where you’re at and what might need to change. And I agree with Stacey, every freelancer has committed some of these.

    • Carol Tice

      I get the ‘you’re a liar’ thing all the time. “You made $2000 on an article? That doesn’t happen…”

      If you can’t believe good pay exists, you’ll never earn it.

      I think the sarcasm in this post partly makes you think about your freelance services from the client’s point of view instead of your own, which is a good thing to stop and do now and then.

      • Linda H

        I’ve learned that marketing is key to getting great paying gigs, and yes, they are there. I’ve gotten a couple that are fabulous and my business is growing. But it’s work and requires discipline and good time management, which I’m relearning..

        When I think back, my dad was self-employed for 47 years, and my grandpa for 40 years before that. They had to do marketing all the time too… only it was called advertising for their brick and mortar store. No matter what you do, if you work for yourself you market. And, as your craft improves you can command higher salary/work rates because you earn the readership and following for the client. Eventually you earn that branding — “Ooooo, an article by Carol Tice; gotta read it I know she’s fabulous!” That’s when it truly pays.

  7. Nida Sea

    These are freakin’ great! I’m guilty of some of these, I’ll admit to it. After freelance writing for four years and making these mistakes, I had to learn them the hard way. But, it pays off when you understand them before making a fool of yourself. Great post!

  8. CJ McKinney

    Well then. Snark is good (my default mode I admit) but really, shouldn’t we be above blaming the victim? Numbers 1 and 9 fall flat in the face of the marketplace. It would be wonderful if everyone could find those lucrative clients and get what they’re worth and all that good stuff. But sometimes, folks, it just ain’t there. Is someone selling herself short because she takes a low paying gig that pays her car insurance? Not devaluing the central point, but every so often pragmatism has to creep in.

    • Carol Tice

      I don’t know…I find the marketplace is usually great for writers who are aggressively marketing their business. For those who rely on Craigslist ads, bid sites and content mills, it isn’t.

      I can’t agree that good pay “just ain’t there,” since I’m watching so many writers in Freelance Writers Den get out and start marketing, and land great pay, sometimes without any clips even.

      Of course, sometimes we all end up taking less than ideal jobs sometimes just for the money…but if you’re never earning what you want, I’d submit that you’re not being victimized by the market. There’s a lot of good-wage work out there for freelancers. Downsizing has only created more opportunity for us.

  9. Mary Sutton

    I only skimmed the bold points. I guess I’ve had my fill of the snarky “Do this” (no I really mean don’t do this)” kind of posts. Seen them all over the place.

  10. Madeleine Kolb


    I liked the post, starting with the attention-grabbing title. It gives a strong hint of what to expect, and providing 23 ways (not 10 or 20) is a bit quirky and interesting.

    Best of all was discovering your travel blog. It looks terrific, and I’ve made a note to go back and check it out more thoroughly.

    Well done!

  11. J. Delancy

    Guilty of 1, 2 and 9. Snark is overdone, but I liked this post because it was actually well-written and funny.

  12. Lisa P

    Without actual examples of what the writer is criticizing, the sarcasm just comes across as generic unfunny ranting. 1. Don’t be a jerk 2. Don’t be stupid……great, thanks.
    It could have been funny with examples drawn from the writer’s experience, observation, or a realistic simulation of bad writing.

  13. Kristi Hines

    These are all so true points. The snark and sarcasm actually make it a refreshing read from the other stuffy posts out there. 🙂

    • Carol Tice

      Well, that’s how it struck me, Kristi — but apparently not everybody!

  14. Ken

    I find the article cool. I also visited Uttoran’s blogs and I found his writings very entertaining. I also admire Carol for not being sorry and standing on her decision to post this article although it might turn off some of her readers. We have different tastes, perspective, and sometimes sense of humor.

    • Carol Tice

      I’m definitely not sorry, Ken — look at the interesting conversation we’ve had about blog tone out of this!

  15. Neil

    I can’t believe you allowed this piece to be posted. It diminishes writers everywhere. The sarcasm flies into the face of seeking to establish oneself. Don’t we feel bad enough without this…this…diatribe into what makes us come across as less professional? Do we have to be reminded that we destroy our own freelance careers by the stupid and lazy mistakes we all make?

    I am sorry carol, but this is totally…right on target. Yes we do need reminders sometimes. if it can be done in a comedic tone, then more the benefit. (see I can get snarky too) 🙂

    Quick question on the tax thing. As freelancers, how often do you file and the best approach to doing it? I worked all my work years where taxes were held out. Now it is my responsibility and need the best advice.

    Thanks again for the great post.


    • Carol Tice

      Ha — you got me there! I was all worried for a minute. Nice job.

      On the tax thing…Your first freelance year, you’ll probably just file at year-end. You can’t really estimate your taxes through the year because you don’t know what you’ll make.

      After that, you’ll be smart to make quarterly tax payments — the next deadline for that is coming up 9/17 (assuming you’ve got a real income coming in).

      I highly recommend working with a tax pro for at least one year to make sure you understand how much you should be sending in quarterly. This will avoid the nightmare where you hit April and suddenly find out you owe $10K or something all in a lump, with penalties for not being a quarterly filer and delaying remitting that money to the IRS. You want to spread the pain through the year.

      On the state level, you can be an annual filer likely until you pass six figures — I just recently switched to filing quarterly with my state as well. Or that’s how it worked in my state. We don’t have state income tax here — so like I say, I recommend working with a business-tax pro at least for a consult to get you set up right.

  16. Garry Stewart

    Your points are utterly true. The impression you create when you start the freelance writing career will determine its future, it’s better to set the pace write at the beginning.

  17. Kata

    You have made such a great summery of the most common blogging mistakes, but it could be interpreted as a great collection of useful tips for beginner bloggers! Thanks for sharing the helpful advices!

  18. Mike

    Honestly, I got a lot of laughs out of this. I am kinda new at the freelancing and learning a lot about my own writing (honestly I suck and feel like it’s still crap work, but everyone has to start somewhere) and realized that there have been a lot of times that I have done one or more of these.

  19. Abby Hayes

    I’ll be one of the writers who loves the sarcasm! But I have to say that #1 isn’t exactly right. I can actually make “decent” money writing for mills because I can write very quickly and often would take on repetitive jobs that involved little to no research.

    But making money from the mills is more dangerous than not making any. It’s hard to break out of something when it really does bring in enough to pay the bills. (Even though it makes you want to gag yourself with a spoon on a daily basis…)

    • Carol Tice

      I totally agree with you, Abby — I’m always saying I’d rather see writers do free samples for quality clients than do mill work…because with pro bono work you never get confused that what you’re doing could be a sustainable living. You know it’s a stepping stone to getting good pay, and you don’t want to do free work very long — you’re motivated to move on and get quality clients.

      When you say you’re able to make ‘decent’ money I’m assuming you barely make your bills…and how long can you write those robot articles about skin diseases or whatever? The problem is, it takes so much time to make that ‘decent’ money the mill way that you never have time to do any other marketing and find better clients.

  20. Kate

    Well, I agree with most of the writer’s points except with #1. We writers do need to get paid and especially if you’re just starting out, it’ll be so awesome just to get paid for writing, no matter how low it is. And it may have a snowball effect too. I’m just starting out but I have both unpaid and paid writing work – the unpaid work is fulfilling and certainly bulks up my portfolio and the paid work pays for the food on the table –literally. #1 – Sell yourself short and often go hungry: ….NOT! A writer’s gotta eat and pay internet bills. By the way Carol, I love your podcast from Blogcast FM – Journey from Blog to Book Deal 🙂

    • Carol Tice

      Thanks Kate! I love blogcast.fm – great podcast if anyone doesn’t know Srini Rao and that great team.

  21. Kevin Casey

    Hi Carol –

    The ‘don’t sell yourself short’ one is huge. There IS good-paying work out there for people who know how to look for it, and expend the energy to go after it. Last week, for example, I wrote 10 blog posts (at $500 a post) for a client I reached out to on LinkedIn months ago (steady, long-term clients are the best!).

    Regarding the ‘tone’ of this post (and the reactions to it), I think the title of this piece may have set up expectations for ‘meaty advice’ that hasn’t been met – hence some readers’ disappointment.

    Keep up the good work!

    Kevin Casey

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