Do You Have What It Takes To Be A Freelance Writer?

Do You Have What It Takes To Be A Freelance Writer-

Here’s the thing: As ideal as working from home (for yourself) sounds, it’s not for everyone.

Not everyone thrives with heavy doses of isolation and self-imposed deadlines while spending hours at a computer. It’s that simple. I don’t know that I’ll ever say someone can’t make it as a freelancer-it’s more a matter of determination and hard work-but there are certainly people who freelancing would make miserable.

Plus, there are drawbacks. * collective gasp *

Yes, I said it: There are actually cons to the world’s most romanticized career arrangement.

I’ll give you a few examples from my own experience:

Can You Handle Isolation?

A lack of coworkers not only means there’s little chance for social interaction during my day (at least until the kiddos get home or if I arrange something) but I also miss out on making friends at a place of employment.

If you require social contact within your day you’ll have to make plans in your off hours and keep in contact with your friends. You’re not likely to run into anyone new while hunched over your laptop, spooning leftovers into your mouth during what you will now laughably refer to as your lunch hour.

That’s not to say you can’t schedule lunch dates and network with other professionals-but the ‘ass in seat’ component of writing means a lot of your time will be spent at the keyboard alone-especially in the beginning. I have yet to find a way to make a living writing that doesn’t involve sitting down and actually, well, writing.


Speaking of sitting, you’ll be doing a lot of it. My last 9-to-5 job before going back to writing full-time was at Wal-Mart. (I know-cliche!) But what I did all day was unload trucks, down-stack pallets and haul freight. It was a physically demanding job and not only did I lose a bunch of weight while working there but I soon learned I could eat whatever I wanted and not gain weight. Awesome, right? (It totally was-I made sundaes in the breakroom all the time for dinner.)

Fast forward to the present and I hate to admit that I’ve put on about forty pounds since making the transition to freelancing. I have to make an effort nowadays to include physical activity in my routine. It’s no longer incidental.

To combat the weight gain, I’ve considered offering Wal-Mart a part-time arrangement where I come in for a couple hours in the afternoon to unload the truck in lieu of a gym membership. It’s not that I need the money so much as a way to turn something that would normally be an expense into income. I am self-employed after all. Plus, not only would I be less likely to skip a ‘workout’ if it meant calling off but the ‘unloaders’ are stereotypically smart-asses and I miss the banter.

If you’re considering a career in freelance writing, I suggest you make a plan to exercise. All those hours perched at the computer wreak havoc on your muscles and joints. Granted, I’ve struggled with my weight all my life so you may not have this problem but, regardless of size, getting your blood pumping improves your mood, boosts your immune system, and delivers oxygen and nutrients to the brain. Obvious benefits, even for those who don’t write.

[Today Was] Just A Day Fading Into Another

100 points if you can name that tune. (Hit me up in the comments!)

But seriously, working from home can create severe work/life imbalances. Be mindful of that as you spend more and more time at the computer. One of the great draws of freelancing is to have the freedom to do things you wouldn’t be able to do while tied to a time clock or traditional employer, yet so many freelancers find that working at home can easily become mindlessly staring at your monitor while the days blur together. Sometimes during a big project, under multiple deadlines or in a frenzy to market for work this is unavoidable, but be cautious of it becoming your new normal. Take a shower. (Yes, I have to remind myself sometimes. Don’t judge.) Make plans. Set a work schedule and decide when you’ll punch out. Eat dinner with your family or housemates every night for a break. (Crockpot recipes, anyone?) Get out of the house. Be a complete cliche and take your laptop to a coffee shop or local park. Bonus points will be awarded if you share a photo #typical. 🙂

Determination Is Key To Freelance Writing

I’m going to lump a lot of beneficial personal virtues under this heading because I could write bullet point after bullet point listing the common traits of successful freelance writers. Oh, to hell with it, let’s do it that way but first let me say this: you will only get out of this career what you work to put into it.

Yes, there is good money to be made selling your writing skills to clients online but freelance writing is no get-rich-quick-nonsense. It’s hard work. Despite the fact that it isn’t manual labor, it is mentally demanding, requires a certain level of motivation and the hours are typically long when you’re first starting out.

Your Freelancing Future

Once established with a comfortable roster of clients and projects, many writers choose to take on less work and less hours. Sometimes this doesn’t amount to less writing time at all but more time spent on a personal blog or passion project – but the ability to do this depends a great deal on how successful you are at increasing your rates and landing higher-paying work as you develop your career. Don’t forget that how much you earn and finding/landing work will be your responsibility once you’re self-employed. You’ll have to advocate on your own behalf and use every new assignment to position yourself for the next one. In the beginning, you may not have the luxury (financially or professionally) of being picky about clients but as you grow your resume and hone your skills, you can and should direct your career path with the assignments you pursue.

Reverse-Engineer Your Writing Goals

Define your wildest career dreams and don’t hold back: Who do you write for? What do you write about? Where is your work published? Does your writing make a difference? Have you written a successful book?

Next, define what would need to be on your resume to position yourself for those assignments and that career. Done? Now go write it down because there’s your new professional to-do list. Half of getting where you want to be is actually defining it and once you know where you want to go, all you need is a map. If you’re dreaming big-and you should be-you might need to take that idealistic resume back a few drafts but you’re in charge of directing your career goals so go for it!

PS: If one of your goals is to write a book…ass-in-seat.

Okay, back to the present and our bullet list of personality traits that go hand-in-hand with freelance writing, but apply to self-employment in general:

Determination: You’re going to have to want it pretty bad to put in all the hours and marketing it will take to build your career. Here’s a statistic for you: 95% of new blogs are abandoned within the first 100 days. Not only should this statement ease your fears of a saturated market, it says something about writing as a whole. To make it into that top 5% all you have to do is keep writing. Most writers that don’t make it professionally either never tried or gave up.

Tenacity: There’s going to be rejection. It’s an occupational hazard. Period. My work still gets rejected and I certainly don’t have a 100% conversion rate on my email marketing. That’s just the nature of it-you’re going to get knocked down. You’re going to be told, “no thank you.” Take a little time to process it if you need to but Don’t Stay Down.

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I once had an email exchange with Carol Tice that put me in bed for two days. It wasn’t that she was mean, she wasn’t. I just had a hard time processing her constructive criticism because of my own fears of professional inadequacy. Plus the woman is HUGE in the professional writing space and I was terrified to have even put myself out there, so it was hard to separate her suggestions from my own professional value. Guess what? I followed her advice and I lived-and I kept writing.

If I can get up, so can you. Send that piece to another publication. Pitch that idea to a different blog. Write something else completely. Send twenty more emails. But for crying out loud, keep working. Chances are, if you’re really dedicated, quitting will hurt more than any rejection or criticism.

Courage: I can pretty much guarantee that at some point in your writing career you’re going to feel insecure or afraid-probably both. It’s a common obstacle shared by artists and the self-employed. It’s normal-another occupational hazard. The important thing is that you don’t let those fears stop you. Courage is taking action in the face of fear. You’re going to do things that scare you. If you don’t, chances are you’ll stay right where you are because change itself initiates fear. But that feeling in your gut is a close relative of excitement. Change how you approach occupational fear and you might start to associate that knot-in-the-stomach with opportunity.

Accountability: I reported to managers of all kinds throughout my years of traditional 9-5 employment. Some I loved, some I couldn’t stand-but by far, my favorite manager of all time is me. I am understanding of my needs. I don’t make myself work when I’m obviously too sick to function. I’m not rigid with scheduling and there are frequent all-nighters followed by mid-morning naps. I give myself plenty of days off and vacation time. I let myself leave work when my kids have a school function or call home sick. I am an incredibly employee-first manager.

That being said, I’m also in charge of making sure I meet my deadlines and have enough work to pay my bills. I have to buckle down when there’s writing to be done. I have to market myself constantly to prospective clients. I send article ideas (also known as query letters) to publications I want to write for-and add to my resume. And I’m also the bookkeeper-slash-budget-committee when it comes to financial records, supplies and service procurement.

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If you’re going to be successfully self-employed, you’ll have to not only motivate yourself but hold yourself accountable for getting things done-otherwise your self-employment will quickly spiral into unemployment.

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Organized: Speaking of bookkeeping as a self-employed writer, organization should be your friend. After all, you don’t have to know where your receipts are at tax time but it sure as hell helps. Your system doesn’t have to be anything fancy or the latest expensive software but you should at least have a specific way to track expenses (physical and digital receipt folders work), queries, income, invoices, occupational marketing efforts and deadlines.

Taxes And The Self-Employed Writer

I won’t go into the details of self-employment taxes here (Freelancer’s Union has life-saving resources on this subject! Scroll down the page for their first-time freelancer filing and tax deduction guides) but working as a freelancer means that you no longer have an employer withholding your social security and tax payments. Since these will be your financial responsibility come filing day, if you’re not expecting a refund your first year of self-employment large enough to cover your tax liability, you’ll need to set aside a portion of your freelance earnings (15.3%) to cover this debt. I also suggest using a trained tax professional your first year filing as a freelancer. If you choose to use software after that, so be it, but an adviser will be able to answer your questions and explain the tax responsibilities related to self-employment. To get the most out of your first year, make sure to save any and all business-related receipts. These deductions will help offset the taxes you’ll owe.

Internet + Computer + PayPal

Since we’re getting into the nitty-gritty of what you’ll need to start freelancing, I want to say now that these three things (internet, computer and PayPal) are the bare minimum. I’m not going to try to cover your website or clips or blog in this (already long) post. We’ll get to those as we work forward, I promise, but here I’m only going to touch on these requirements, and one other that we’ll discuss in a minute. Obviously these assets are self-explainitary. You have to have the necessary equipment and reliable access to work online. As for PayPal, you’ll only need an account if you value being paid-and might I recommend their Business Debit Mastercard, if only to avoid the 5-day-delay-headache of transferring money to your bank account.

Skilleezz That Pay The Billeezz

Double the E, Double the Z, Double the Flava.

Another 100 bonus points if you know the movie! (Cause I’m a big dork and don’t mind it showing!)

I saved this requirement for last because a lot of would-be freelancers don’t like hearing this little tidbit. Since you’ve made it through this monster piece of content, I assume you’re serious and deserve to hear the truth, no matter how unpopular.

So here it is: If you plan to sell your writing skills to clients online, you have to have writing skills to offer.

I know. Mind-blowing. Now, you don’t have to be the reincarnation of Allen Ginsberg (or any other iconic author) to make a living from your writing, but you do have to have a reasonable amount of skill. If you’re expecting clients to pay for your services you have to be able to deliver. It’s that simple.

Here’s the good news: You don’t have to be a skilled writer right this second to succeed at freelance writing. I’ve said skill now like ten times-and skills can be developed. And if you used to write but haven’t in a while, chances are you’re just rusty. The fact of the matter is that if you don’t currently have marketable skills, you should get to practicing.

It’s a great excuse to start a blog or submit some on-spec assignments, where you submit a completed article to a publication instead of relying on a query and your qualifications. Lots of websites accept on-spec submissions and they’re a great way to get your first clips. I’m currently curating a list of links to these markets for you and will add it here once it’s available. If you don’t want to have to check back, you can subscribe to the weekly newsletter below and I’ll give you a shout as soon as it’s available.

The point is, if you’re not writing already-you need to be. Practice! Build your writing skills so you have something valuable to offer. Eventually clients will be lining up to book your services.

Also, experiment with different types, tones and formats of writing. There are TONS of writing opportunities out there if you’re willing to try something outside of the traditional article. I list almost twenty-three pages of them in my free ebook, 50+ Writing Markets and Resources to Get More Clients and Increase Your Income, and you can get your copy through that link.

I can’t stress this enough to new freelancers. While it can be a lucrative market (and one hell of a portfolio-booster), there is so much more to freelancing than magazine features, though this seems to be what many aspiring writers are focused on. If your writing goals include glossies (major magazines) that’s wonderful but don’t discount other avenues of income.

Professional Development

I’m going to wrap this up with the three best pieces of advice I have for new writers:

#1 Study Writing And Content

Plan on writing digital content and blog posts? You should be reading up on ways to boost your assignment’s SEO, studying content marketing, examining the different elements of digital content (links, marketing outreach, affiliates, format, etc., etc.), and researching blogs BEFORE you pitch or apply to them. I have a pre-pitch checklist over on BeAFreelanceBlogger that will guide you through what to look for and can easily double as a study guide.

If you’re dreaming of the lucrative copywriting market, look for examples of sales letters online-and in your mailbox. Study landing page design and sales funnels and automated email marketing. Google websites dedicated to copywriting and search for self-imposed sales-copy assignments.

No matter what type of writing you plan to pursue in your career, look for examples. Study them. Find people who specialize in it and follow them on social media. Search for websites that talk about it in-depth and read to your heart’s content.

This career-centered study that benefits your writing career is called professional development, and it should be constant throughout your entire writing career.

#2 Write, Write And Write Some More

If you’re serious about your career-level writing goals, you have to write. I know it seems logical, right? But you’d be amazed at the number of people I talk to who haven’t written anything other than a check since high-school but ask me for advice on breaking into freelance writing so they can quit their jobs and stay home.


Sadly, that’s not usually the answer they want to hear.

#3 Put Yourself Out There

It’s a common pitfall of new freelance writers-you spend so much time reading and studying the industry that you fail to ever get started taking on work. Yes, it’s scary. Yes, it’s overwhelming. Do it anyway.

Check out what’s posted on the job boards (these ones are worth bookmarking) and send out a few emails. I highly recommend having experience, clips and clients BEFORE you make the leap to full-time so you’ll have to start some time. Have a unique experience, story or information to share? Write up a query email and submit the piece to a publication that would be interested. (Again, scope out the publication first to see if your article will ‘fit’ or you’ll risk looking like an ass.) Brainstorm ideas for publication-specific on-spec articles…then write and submit them!

Building a freelance writing career is by no means impossible, though it can be overwhelming when you’re just starting out. Thankfully you now know what to expect but there’s still so much to tell you! That’s why I developed this series for aspiring freelancers, so you have all the information and guidance necessary for success.

I’ll be adding content to this series as it becomes available-and updating the links below. If you want to avoid checking back here, which just sounds like a pain, subscribing to the newsletter is the best way to get real-time updates about what’s new on Paid Write, though I share fresh content on the PW Facebook page, too!



And don’t forget about those bonus points! I can’t wait to see your answers. 🙂

Other Posts In The ‘Get Started Freelance Writing’ Series:

  • Use Your Clips to Land Work
  • Land Your First Clips
  • What Will You Write About?
  • Your Niche Is More Than A Topic
  • Build Your Professional Website
  • How A Blog Can Help Your Writing Career
  • Should You Blog?
  • 6 Ways To Land Work As A Freelance Writer


I spent years working low-paying jobs. I’ve been a cashier. A line cook. I unloaded trucks. These days I support myself and my children with my writing. It’s a new and exciting life – and I want the same for you!

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