5 Signs it’s Time to Quit Freelancing and get a “Real Job”

freelance_help_wantedBy Daisha Cassel

If you’re doing it right — and making a good living off it — freelance writing is a real job. In fact, most successful freelance writers put in well over 40 hours a week when they are getting their businesses off the ground.

Unfortunately, though, a lot of wannabe writing pros are unprepared when they decide to take the plunge and go freelance. Here, 5 ways to know that it’s time to say sayonara to the Schedule C and start sending out your resume.

1. You’re on the verge of bankruptcy and your basic needs aren’t being met.

You don’t have two nickels to rub together…and you’re in dire straits! But you think freelance writing will net you fast, fast cash.

There’s a reason you’ve never seen a late-night infomercial or a back-pages ad in Popular Mechanics touting this profession as a get-rich-quick scheme. Not only does it take skill and hard work, but it’s one of the worst jobs to have if you’re already living paycheck to paycheck.

Unlike a job with an employer, you can’t count on a weekly or bi-weekly shot in the bank account. (One high-profile newspaper once took seven months to get a check out to me, and many freelancers have horror stories of never getting payment from shuttered mags and deadbeat publishers.)

Let’s not forget that the old adage “It takes money to make money” applies here too. You’re not sitting around in a safari jacket scrawling your next magnum opus with an affordable feather pen, are you? At the very least you need a reliable computer, internet connection, and phone to function as a business. It’s hard to focus on an interview when can’t pay the bill for the cell phone you’re conducting it on.

And “basic needs” are more than food, water, and those two proverbial nickels. Do you have health insurance? Are you contributing to a self-employed retirement plan or IRA? Do you have an emergency fund to cover those times when you, too, might wait seven months for a check to come in?

If your basic needs aren’t being met, you may want to consider seeking out employment until you’re over the hump.

2. When you read the beginning of this post you wondered, “What’s a Schedule C?”

Writing can be a hobby, but freelancing is a business.

When you go into business yourself, you are your own employer. This means things that your boss or the company accountant did on your behalf when you worked a 9-to-5 are now up to you.

It’s a legal requirement that you withhold and pay your own federal, state and local income taxes. (And guess what: since employers chip in to their employees social security and Medicare tax contributions, and you are now your own employer, your bill could be even bigger.)

If you haven’t been sending in tax payments, or even filing taxes on your earnings at all, you’re not just in violation of the law — you also aren’t treating freelancing like a real job.

3. You get nothing but rejections–and that’s on a good day.

“Nice” rejections where editors and clients ask you to stay in touch are one thing. But if you’re pitching plenty and hearing back never, or you only get boilerplate rejections, it may be time to reconsider the source of your future income.

If you don’t know when you’ll land your next article, then you don’t know when you’ll get your next paycheck. That uncertainty leads to desperation — both financial and emotional. It is one thing to be perseverant and another to be a glutton for punishment!

4. You’re amassing clips and experience, but not cash.

You’re writing for pennies a word (or less!), but your big break is right around the corner, right?

Don’t count on it.

Many a fledgling freelance writer has toiled away for far too long in the depths of content mills, (very) small regional magazines, and other no-or-low paying gigs in the name of “getting clips and experience.”

Sure, you need to have clips to show off your mad skills, but editorial standards tend to be as low as the pay in these cases, and no editor will be impressed by a barrage of hyperlinks to penny-a-word articles.

My advice? Completely skip the content mills, and start pitching to the big boys as quickly as you have a good idea. Most editors will be more receptive to a great query supported by a single clip than a mediocre, poorly researched one with lots of mediocre clips.

If you just can’t bring yourself to pitch high-paying markets, it may be time to consider getting a job and relegating freelance writing to “hobby” status.

5. You’re more worried about keeping up appearances than making a living.

A reader recently wrote in to Linda saying that she is on the verge of bankruptcy, and freelancing hasn’t worked out for her after several attempts, but she finds the idea of working in retail or food service “distasteful.”

Personally, I have a greater aversion to not having a paycheck when the mortgage is due and there’s no food on the table.

Maybe you made a big to-do about leaving the rat race behind, and now…it?s not going so well. This is important, people: do what you have to do to make things work for you financially.

If you love writing and feel like you just need a little more momentum, then keep it up as a second job while you take on something that pays the bills. Once it really does pick up, then you can slide back into a life of writing full time and kick that other job to the curb.

In the meantime, there is honor in doing what it takes to support yourself and your family. Think about it: would you rather say out loud that you are taking a new job in addition to your writing so you can pad your bank account, or that you don’t have enough money to feel your family and keep the lights on?

Bottom line: freelance writing can be a satisfying and lucrative work, but it takes a greater commitment to be your own employer than it does to be an employee. Do you have any other tips for fellow freelancers about self-employment? Share them in the comments below.

Daisha Cassel is a freelance writer who keeps four nickels in her pocket at all times just in case she ever wants to experience the luxury of rubbing two nickels together in stereo.

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58 comments… add one
  • LOVE this post Daisha! You’re really getting the skeletons out of the closet there.

    Writers don’t want to look in the mirror and ask these questions…but they should.

    • Daisha

      Thanks, Carol!

  • Matt

    Well said!

    I especially like the part about pitching to the big boys as soon as you have a good idea. There’s always the most competition for the lowest rungs of the ladder.

    All the best!

    • Daisha

      “There’s always the most competition for the lowest rungs of the ladder.”

      Exactly! I hate to see writers who think they have to fight for scraps in order to pay some sort of mythical dues. Thanks for reading, Matt.

  • Filing this one away, yet hoping I won’t need it. Harsh and necessary.

    • Daisha

      Kelly, you’re in a good place if you can read this as a gut check rather than a wake-up call!

  • Cheryl Rhodes

    Sorry I didn’t like this post at all. Especially the headline and this quote: “Personally, I have a greater aversion to not having a paycheck when the mortgage is due and there’s no food on the table.

    There are many people who may or may not be writers who are unemployed, under employed, or hours have been cut, who don’t have a paycheck and are freaking out because the mortgage is due and going hungry. Telling them to go out and get a job when they’ve likely been desperately searching for work for some time is insulting.

    Whether or not a person can find freelance writing opportunities easier than finding a real job is hard to say but might have been a more interesting read.

    • Daisha

      Wow, Cheryl, you must have really hated those two lines… it seems like they stopped you from reading the rest of the post! The specific example which you noted is of someone choosing to not go out and find other work when she acknowledges her freelance career isn’t cutting it financially–not a desperate unemployed person. I agree that it would be insulting to tell people who have been searching for employment to “get a job.” That was not one of the messages of this post. This is a writing-specific blog, and the advice presented is specifically intended for freelance writers. The “real job” referenced in the title (with tongue firmly in cheek) is an alternative for a self-employed person who would be better served by traditional, employer-based work.

      What I’m troubled by is that some of the content in your response indicates that you think a freelance writing career is a stopgap for someone who is already in a desperate financial situation. That’s not the case, and if anyone is coming to The Renegade Writer with that idea in mind, they would be served well by reading this advice. It’s important for all fledgling writers to know the realities of the market and the job.

      • I find this response to Cheryl to be quite condescending. She knows this is writing specific. I, too, have found rates in the past five years to be dropping or subsistence, and many new editors coming on the scene are inexperienced in communicating and it’s like pushing a string to book a job–the conversation in email folds back on itself. Do you want to assign it? What does it pay? Could you actually pay X? This is not the business it was–and I am not talking about the schlock shops, either–I am talking about pubs like the Costco magazine, Washington Post, Medical Economics, and others.

        • Star, I don’t want to be rude, but all you seem to do on this blog — for the last several years — is complain about the writing industry. Daisha makes a good living writing — I know because we talk often. While my career has shifted between different types of writing depending on the industry and my mood (right now it’s content writing with a little mag writing thrown in), I haven’t even seen a dip in income or opportunities since I started in 1997. And I know dozens and dozens of people making a good living as writers, possibly because they see the positive and know how to roll with the changes in the industry.

          • Star

            I haven’t posted here in a year, probably. And won’t again. Your guest was saying the same thing I was, by the way–that you have mhave to augmnent with a “real job.” My friends and I also talk–and our experience is different.

  • This is excellent, very precise advice. I have never been brave/foolhardy enough to go freelance full time. Very few people in my region–a midsize city in upstate N.Y.–can earn a living exclusively by writing freelance. Most writers I know have several gigs, including teaching at local colleges. And these are writers with decades of experience (and often master’s degrees, which qualify them to teach at the college level).

    • Thanks, Reid! I’m not sure Daisha is saying it’s impossible to make a living exclusively through freelance. LOTS of people do it, and from all regions. With the Internet, you’re not bound by your region…you can freelance from anywhere for markets all over the globe. Don’t forget Bamidele Onibalusi, the blogger who writes from Nigeria and seems to be doing pretty well with it!

      • But don’t you have other gigs–yoga teaching at one point?

        • No. I burned out 2 years ago and became a personal trainer for a few months, but I got my writing mojo back quickly and returned in full force. All I do is write, and teach writing.

  • As always, good information. With a full time job and a blog that is quickly becoming all-consuming, it can be difficult to figure it all out. Yes, the blog isn’t paying me (do comped ballet tickets, the chance to interview the dancers, and review a ballet count?), but I do feel it is “right around the corner.”

    I have interviews for my blog site with several known and professional dancers. I was approached by an English dancer asking to be interviewed and by a US ballet company that wants me to choose dancers to highlight. My goal? To turn the shorter blog stories into full-fledged magazine articles. Kind of the girl-next-door can get the story that your dancer-next-door readers really want to know.

    It’s nice (and scary) to hear it in “real talk” that you don’t get paid every two weeks with mileage and vacation days. Yet, you motivate me to push harder to get where I want to be. Keep up all the fabulous posts. It’s what fuels my writing fire! Mwua to you!

    • Thanks Kristin! I’m glad this motivated you…the goal of this post was to motivate those who are in it to win it! (How’s that for a clich?”)

      • Star

        I choose it to lose it, I guess. Well, I know my thoughts from 35 yrs as a full-time freelancer are not wanted.

  • Trish

    This is a very important post and makes solid points. I’d like to add that first off, anyone who thinks that seeing their name in print is more important than telling a good, strong, alive story, well, you deserve the content mills and small potato magazines. . .and the zero money that comes from putting narcissistic byline bliss above the integrity of the journalism trade. Making it as a freelance writer is a hard road …it is hard the way art is hard. The people that are able to make a living are those who understand that their role is to let the story be the star and not themselves. My dad was a daily metro newspaper vp and he told me that if someone writes a fascinating query that has a voice, whether or not that writer has clips, he would assign that story. Some pro writers get lazy and develop a sense of entitlement, some people want to see their name in print and pitch vague junk, and other writers are passionate, hungry and do their homework. There is always room for the latter and these are the ones who will get in. Being a successful freelance depends on snagging a few bread and butter clients; then you can do a story here and there to up the ante and network yourself. It’s a lot of work. Sometimes I am filing a story at 3am and wonder what the hell am I doing in this business. But then I get a nice check, read my story, get another assignment and I know this is what I was meant to do.

    • Daisha

      Trish, I think you are absolutely right that the gears of content mills are often turned by writer ego. Linda has said before that she often asks students if they want to get paid, or see their name in lights. It’s easy to “get your name out there,” and much harder to make a solid living with the pieces that follow the bylines. I’m glad to hear that doing the hard work brings you so much satisfaction!

      • Trish and Daisha, I love both of these comments. I don’t think you can go into writing without a little bit of, “I want to see my name on that great story,” but obviously the story needs to be the focus. If it isn’t? Well, you name won’t get the notice. When I blogged and wrote before, I didn’t find my voice or a direction. I had a newspaper column that was my view of the world (so to speak) and that is when I found the tone with which I wanted to write. I write very much like I speak. It works for me.

        Now that I found my focus (ballet writing/reviewing,) my blog is doing wonderfully, and I’m getting amazing writing opportunities (including comped tickets, dance clothes, etc). But, still not making money, which is why I am keeping my day job, for now.

        Last week, an opportunity came around to pitch to a business owner who is a photographer. Now I’m finding “her” voice and will be writing much more professionally because that is what she wants.

        Ballet is my voice, photographer is hers, only with my words. I feel that if you get one foot in the door and crank out what the client wants and needs in a timely and professional manner, it still won’t be easy, but you can begin to journey to the land of no more “real” job.

        Thanks, Renegade Writers! You inspire me!

  • There are some interesting emotions going on in the comments here, Daisha. Yikes!

    This advice works for any type of business, and not just writing. I hate the ‘just keep going’ advice – it takes a mature outlook to decide to take a job to keep the life basics going – and then come back to the business.

    There is dignity in looking after yourself – the struggle isn’t glamorous. Once the basics are taken care of, the mind is clear to focus on the reason why the business didn’t work and take a second stab at it.

    • Daisha

      Thanks Razwana, I’m glad you appreciated the spirit of my message, which was that self-employed business people can’t treat their careers the same as they would a hobby. You’re right: there is dignity in looking after yourself! Perfectly stated.

  • This post affirms that the decision I recently made to look for traditional employment to secure my finances. Thank you Daisha! I was starting to feel like a failure about it – until I read this post. My plan is get a day job and work part time as a freelance writer so I can build my business the right way. I’ve been freelancing for 2 years, but never made any real money from it. I was stuck in content mills, had a sub-par writer website, and wasn’t marketing myself. My lack of success was due to lack of knowledge (and quite a bit of fear.) I’ve only recently begun learning what it REALLY takes to be a successful freelance writer. With great resources (such as this blog and Make a Living Writing) and my family’s support, I believe I will find success.

    After reading this post, I’m inspired, and no longer feel the shame of going out to get a job. The way I see it, it’s better to start your journey over to find a well that’s full versus tapping against the same barren well hoping water will magically appear (while you slowly die of thirst in the process.)

    • Good for you, Shawanda! I know it feels like giving up, but really you’re giving yourself a better chance at freelancing success by making sure you’re well takjen care of before you jump into this tough career. Let us know how it goes!

      • Nancy

        Hi Linda,
        And other advice from books I have bought state that you can’t have two “masters” – if you are doing freelance writing in your spare time, it is much harder to break into it as a full time job. So what is correct?

        I teach English full time, and by the time I get home at night, I am burnt. I don’t want to sit and write at all. And the books I have bought, and the websites I read and have joined, including the Writer’s Den, I just don’t know that I am getting advice that I can really use. I am just getting more confused.

        • Hi, Nancy! If you’re working a 9-5, you HAVE TO write in your spare time…many writers do that before they make the leap. You won’t likely replace your entire income, but you want to have at least some cushion and a few clients you can rely on before you quit your job.

          But all the advice you’re gleaning from these sites and books is useless if you simply don’t have the energy or motivation to write.

          Email me and I’ll send you a free copy of my new e-book Write Your Way Out of the Rat Race…And Step Into a Career You Love. It has some info on finding the time, energy, and motivation to build your freelance career even if you have a job and a family.

    • Daisha

      Yup, nothing shameful about taking care of yourself! And keep in mind that once you have the stability of another income, you can send out pitches for higher paying publications that you might have psyched yourself out of before when you just needed *any* writing assignment.

  • Candice Lombardi

    Good morning – this is just what I needed to read this morning. This is me. It is so sad to be in this situation because I put my heart and soul into trying to make the freelance switch. Perhaps others can relate. I have gotten gigs and assignments, but they are either short-term or do not pay well for the time it takes to write. How can a writer tell if they are choosing the wrong industries or markets to target? If it’s possible to be very successful in the freelance world, and one gives it 200%, any suggestions on how writers can pick the industry that will ultimately afford them to write full-time? Thank you so much in advance for your advice! 🙂

    (p.s. My full-time salaried background is in grant writing, IT research writing, and newspapers. I have lots of writing experience but it hasn’t translated for freelancing. Yet, I’m burned out of the 9 to 5.)

    • Daisha

      Hi Candice, I’m not sure what you mean about picking the best industry… are you talking about finding a niche, or are you interested in business writing and targeting specific industries (i.e. tech writing)”

      • Candice

        Hi Daisha,

        Thank you; that is a great question. I have asked myself that since I commented yesterday. I’ll say that I continue to have a lot of clients for business writing and IT research–both previous and new clients. I have regular, monthly work from at least four clients. Today, I did two things in response to your article: I booked two tutoring gigs with Calculus students for increased revenue, and I studied new markets for pitching articles (Entrepreneur magazine is one–I also own an e-commerce store and can think of a number of articles to pitch.) So your blog spurred me to keep find additional revenue and assess what my niche is. Needless to say, you helped me answer this question!

        • Daisha

          That’s great, Candice! Looking around at your own life is often a good way to identify your niche–as you’ve done by noting e-commerce as a possibility to write about. You may have read in some of Linda’s posts that her husband Eric writes almost exclusively about board games. That’s one of my favorite examples of a niche that many would think is too narrow, but he’s making a living writing about (and editing content about) something he really loves.

  • I’ve thought about freelancing, but I wouldn’t quit my teaching job at the college.

    • I totally understand! One of the writers I interviewed for Write Your Way Out of the Rat Race…And Step Into a Career You Love actually has a great, high-level job that she loves, and freelances on the side.

  • Great post Daisha!

    Indeed, I think a lot of people struggling because they fail to treat freelancing like a business. A business means you pay your taxes, it means that you probably won’t make much money for the first few months as you build connections, and it means that you definitely have to be committed!

    My tip is – develop a solid plan and be in it for the long haul. It might take a month or two, but your business will gain from making a serious upfront investment.

    • Daisha

      Good tip, Daryl! I’ve definitely noticed that many people see “freelancer” and “business owner” as two totally separate things. I think that people who aren’t in the thick of it themselves often think freelancers don’t deal with their own taxes or marketing and the assignments come to us as fully imagined ideas that just need to be put into flowery words… I wish!

  • Thanks for the “inconvenient truth.” Freelance writing is just like any other career. Not everyone’s cut out for the work, and that’s perfectly okay. It’s no different from an architect who realizes she’s not in the right career, or an engineer who realizes she’s better suited for other type of work. It’s not always a reflection on the industry if some people aren’t successful. We have to find the career that’s a right fit for us.

    • Daisha

      That’s right, Sarah! Add in the fact that some people just aren’t cut out to be self-employed, and freelance writing can really be double trouble. In fact, I think most people who end up burning out in this job are good writers, they just aren’t used to juggling all the tasks that comprise the business side.

  • Dear Daisha,

    I am professional writer and looking for freelance work so may i know that where i can get freelance content writing or freelance article writing jobs ?
    Please update ASAP.

  • Hello Linda:

    I’m writing to say that I have read all three of your books, and they were great! I started with the Renegade Writer, and just finished your most recent Kindle book, Write Your Way out of the Rat Race.

    I’ve been writing as a freelancer for quite a while, and have to say that these are probably some of the best books for beginners (to experienced) that I have come across. I got quite a few ideas myself.

    Thanks to Linda for all great advice in the books. You really should be charging quite a bit more!!

    Thanks much,

    PS: I’m not quitting freelancing to find a real job. I just wanted to leave a post! 🙂

    • Wow, you’re a fast reader! Thanks for reading my books, and for your kind note!

      • I got it and read it… now, I will tweet it for the sweet price you were offering! Thanks again. -Adam

        PS: Don’t wait around for this book to go up in price!!

  • Nancy

    I don’t like this post either. As a person who is new to freelance writing, I have received rejections or not heard back from most of my queries. I guess I should quit and leave the writing to the real writers? Like you?

    That is the tone I am getting from this post. Now perhaps you didn’t mean to create that tone, but as one who makes a living from words, you might have been more sensitive to how discouraging and negative you sound.

    As for me, I will keep pitching and see where they chips end up falling –

  • It simply takes hard work, and plenty of it! If you are making a few dollars here and there and still living at home by the age of 27, then I’m sorry. You need to get a real-world career going so you can support yourself and you have to work twice as hard at your craft when you are not working at your primary job in order to chase your dream of freelancing.

    I am amazed at how many people think they can keep mooching off their parents until they are well into their thirties because they can’t get their life together.

    Hard work = success in the end, every single time!

    • Thank you, Andrea! I’m with you. It’s a hard truth, but that’s the way it is.

    • KLG

      You’re kind of condescending. Telling people to stop mooching and get a real job is basically saying you have no clue what the economy is like. I graduated a month ago and in this time, I’ve only found admin assistant positions that have not gotten back with me. Why would that be? Overqualifications, too many applicants, etc. Within this month, I’ve been pushed harder than I thought I would ever be just to stay alive. And no, I don’t want to stay and “mooch” off my folks, believe me, they’re crazy, but you are incredibly insulting. You are insulting my and other unemployed young adults’ dignities as people by implying we are CHOOSING to stay out of work.

      I am not an idiot. I know what the real world is like. I have severe anxiety and probably depression too, and have been tempted several times to slit my wrists because yes, that is how bad it is out there. I’m probably going to end up teaching and, or, returning to grad school. But don’t look down upon us just because we’re still living at home as we sort things out. Right now, I am freelancing in addition to jobsearching because I want to show I’ve done something during my job search and to stave off the depression that stabs me constantly.

      Sorry if I came off as harsh, but you really depressed me.

      • Hi KLG,

        I just wanted to write to you to say how sad I am for how you feel; I can’t imagine what it must be like to have those worries. Not responding to the other comment about mooching but rather the article, I think it is aimed more at a mid-career person (who probably built up a resume prior to the recession and then left to become a full-time freelancer). I am one of those people. I am not sure if this will be of any encouragement but I struggled to find more than a minimum wage job after college for a year in 2003, and also lived with my parents during that year. Even after landing an administrative assistant position in 2004, it took two more years before I could get into the field as a temp editorial assistant, which led to assistant editor in 2007, grant writer by 2009, development manager by 2011, and now freelance with a full-time consultant contract. I know I got a leg up in a better economy, but still I lived at home for a year after a successful college career, only to work at a convenience store for six months. I just hope and pray that you can keep the faith and trust that you are doing all you can and deserve respect and credit for all of your hard work and efforts. I respect you and hope for good things to come your way. All the best, Candice

  • Lorianne

    I also take issue with some of the content of this blog post and especially the smug, condescending nature of some of the comments. A LOT of people are freelancers, contractors, temps, etc. because employers refuse to hire anyone for full-time work anymore. That’s an exaggeration of course, but the reality is that so-called “real” jobs are hard to come by and have been for years. I personally try to get by as a contract worker because I’m 55, over-educated and cannot even get responses to my resumes and job applications, much less interviews. I have to deal with the probability that I will never find a “real” job. And don’t tell me to apply to Starbucks, etc. as a survival job because I have. I’m counting the days until I turn 62 and can start collecting Social Security — that is, if Social Security still exists by then.

    P.S. Content mills pay for crap but their appeal is that they do offer at least the illusion of regular, dependable pay. It’s also all well and good to tell people to build up an emergency fund. I used to have one. But guess what, after months and years of no work, emergency funds tend to be depleted. And telling someone to hold out for better freelance pay weeks or months down the road does no good when there’s no food in the house and by the way, you have to pay rent TOMORROW or you’re out on the street.

  • Bethany

    Thanks for this awesome article! I relocated with my husband who has a good full time wage (I am incredibly lucky to have him in ALL the ways) straight after I graduated with a science degree. There’s only part-time retail up here, none of the opportunities or connections like at home. I’m quitting my job and trying freelance writing for two years max – if I don’t match my part time retail income in that time, I’m going back to ‘real’ work.

    I’ve been reading entrepreneurship books and articles for months now, and will shortly register as self-employed. I’m also well versed in branding and marketing – writers cannot live by the strength of their words anymore, you’ve got to sell yourself! I’m also building my knowledge of HTML, CSS and Wordpress so A. I don’t have to hire a designer and B. to help my CV if I need to job search again. Personally, I can’t wait to find out how I do. Here goes!

    • Yes, marketing is such an important skill! Most writers don’t know that they’re also marketers — at least if they want to earn from it. 🙂 Good luck on your new journey!

  • A

    The fact is NOT everyone is cut out to make a living as a freelance writer.

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