What is the Most Challenging Part of Running a Freelance Writing Business?

We all know that there are a lot of great things about freelancing — like flexible schedules and the stereotypical fuzzy slippers while working (yeah, I wear 'em). But there are also plenty of challenges.

So out of curiosity, what has proven to be the most challenging part of being a freelance writer for you so far?

I think the most challenging part for me was earlier in my career when I didn't have a solid support network. My friends didn't quite "get" what I did. And my immediate family didn't seem to take it seriously. For quite some time, my mother kept giving me job ads from the Sunday paper with the unspoken "get a real job" hanging in the air. Fortunately I overcame that challenge (funny what a wad of cash can do, eh?). But I'm sure I'll have others.

What challenges have you faced, or are you facing now? With a bit of luck, maybe other AFW members have been in those shoes and they'll be able to offer a bit of inspiration.


Profile image for Jennifer Mattern

Jennifer Mattern is a professional blogger, freelance business writer, consultant, and indie author. She runs numerous websites & blogs including All Freelance Writing, Freelance Writing Pros, NakedPR, and Kiss My Biz.

Jenn has 25 years' experience as a professional writer and editor and over 20 years' experience in marketing and PR (working heavily in digital PR, online marketing, social media, SEO, new media, and thought leadership publication). She also has 19 years' professional blogging and web publishing experience (including web development) and around 18 years of experience as an indie author / publisher.

Jenn also writes fiction under multiple pen names and is an Active member of the Horror Writers Association.

Subscribe to the All Freelance Writing newsletter to get freelance writing updates from Jenn in your inbox.

11 thoughts on “What is the Most Challenging Part of Running a Freelance Writing Business?”

  1. Marketing, marketing, marketing.

    I’ve dabbled in freelance over the years, always while keeping a steady job… many of them! It’s always been the marketing end that has held me back.

    I’ve started a Facebook Profile and a Page for my writing and editing business, but… I don’t know where to go from here.

    I’m a hopeless old Hippie. You know, money is the root of all evil, watch out for the Man, man. Yeah, I did the commune thing, lived in a teepee, grew my own granola, hugged trees till they squeeked.

    Now my pony tail is gray, my teepee quietly moulders in a barn in eastern Wyoming and I get my first Social Security check in September. I’d feel bad about growing old if it weren’t for the alternative.

    So I need to learn about marketing and making money. I hope someone here can lead me in a direction, right of otherwise.


  2. Hi there Michael,

    Marketing is actually one of my favorite parts of freelancing. Then again, I’m probably biased as I come from a marketing and PR background.

    Don’t stress too much over the marketing side. A lot of writers are turned off by the “gimme gimme” aspect of hard-sell marketing and sales. Fortunately there are other ways to go about it such as networking to build referrals and building a platform to help clients find you instead of you always seeking and pitching them. That’’s actually the topic of a book I drafted last year (currently in the first major round of edits) called The Query-Free Freelancer. You can also find information about query-free freelancing on our blog.

    The idea is simple. You build visibility through your network and platform. Most of the great freelance writing gigs aren’t publicly advertised (so don’t let low-balled offers on freelance marketplaces deter you in any way). They’re landed via referrals and things like search engine rankings as clients search for the specific writers they want rather than hoping to find them from a pool of applicants.

    Building a professional website and optimizing it (in a non-spammy SEO sense of course) is a good first step. If you have one, you can then link to it in blog comments or in forum signatures here and elsewhere. That’s one way to build visibility. I highly suggest launching your own blog if you dont have one. Readers and search engines both love them because they’re more frequently updated than static websites.

    Hope that gives you a starting point!


  3. the most challenging aspect for me is the uncertainty, in terms of work and pay for the work. i’ve been doing freelance writing and editing full time for more than two years. some months are better than others but that’s ok it’s part of the gig. what i’ve noticed to my distress is that when i don’t have a big editing project in hand for instance, i have to write much more for much less pay than when i started because the clients who pay well are cutting back and pay scales as a whole are under increasing pressure. that squeeze makes it tough, interesting and oddly satisfying when i get through another month with the bills paid and some food in the larder.

  4. I haven’t found that higher paying markets overall are cutting back. In fact, new ones spring up every day. But they don’t often advertise, so the key is to tap your network and build your visibility. You see, in addition to new markets, new freelancers are also jumping in (recent graduates, people who were laid off, those simply looking for a change, etc.). So when a client advertises offering a good rate, they can be completely bombarded by applications — often from people who don’t meet their requirements, but who apply solely because the client is paying more than most other advertised jobs.

    A lot of buyers don’t have the time to sort through that kind of mess, so they stop advertising altogether. Instead they ask people they trust for referrals (why it’s vital to build your network) and they search for writers themselves (why you want to appear high in search engines and build visibility through social media).

    In my experience, the bigger your platform (the bigger the audience you have on a regular basis) and the bigger your network of trusted colleagues and past clients, the more stable freelancing becomes. While I’ve had the occasional project cancelled at the last minute or postponed, I can always reach out to my network now and fill that time quickly. So there hasn’t been a true “feast or famine” cycle in a very long time.

    So maybe the trick is to try something new with your marketing. I’m not sure what you’ve done up until now, so I can’t give you more specific suggestions. But if you check out the link in my previous post in this thread (about 30 ways to build your writer platform), you might find a few ideas you haven’t tried yet. 🙂

    Best of luck in overcoming that challenge!


  5. Jenn, I think the challenging part is training ourselves to shift gears (and marketing methods) when things aren’t going as we’d planned. I look at how my own career has morphed – in early 2010 I was the Blog Queen, writing seven blogs a week. Later that year, I was Referral Queen, having gotten most of my work through referrals. The beginning of this year, I was Whine Queen (the work had dissipated). LOL Actually, I transitioned into magazine writing again, which has sustained me until recently, when I transitioned again into blog, resume, and client project work.

    Being able to shift gears like that is essential. It also means we need to change up our marketing plans to try capturing untapped areas. I don’t see too many writers making that a successful transition.

  6. Sometimes for me the biggest challenge is interruptions from neighbors who see that I’m home and forget the “work” part of the whole work-from-home equation. There’s one person in particular. For the longest time if I didn’t answer her call or return a call immediately, she’d walk up to my house and start pounding on the door. (I do have a doorbell, but apparently it’s not as dramatic as pounding on the door.) I think I’ve finally gotten through to her.

    Other than that my real challenge is maintaining a steady cash flow. I can have thousands of dollars worth of invoices out there and ready to be paid, but now and then a slow payer will mess everything up. Luckily I have a handful of long-time clients who have very regular payment schedules, which helps off-set the slow payers. Yes, I am persistent in demanding that the slow-payers pay. I always remain polite and direct, but each subsequent communication becomes increasingly terse.

  7. Lori — That’s very true. As much as there’s a certain amount of stability in our diversity of work and clients, things do happen that force us to change course. But hey, staying on our toes is partly what keeps this work interesting. Smile

    Paula — Oh wow. I think a neighbor like that would drive me insane.

    As for the slow payers, are you in a situation where you could tell them if they pay late again your payment policies with will have to change — up front payments required — for subsequent work? I charge almost all clients that way. They don’t complain, they pay before they get my time, and I don’t have to chase things down. Unless we’re talking about print publications or some other market with antiquated systems where they think the customer gets to set the payment terms, you might be able to try that. And if you already have a solid history of delivering on time on your end, they really don’t have a good excuse to refuse unless the late payments are intentional. If that’s the case I’d just keep putting feelers out and replace them once new clients come along with a bit more respect for you and the services you provide.


  8. I would never recommend putting off your professional website. Not only do you want your website indexed as soon as possible so prospects can find you, but your website is a portfolio piece. It gives you something to direct people to if you pitch them, it lets others easily refer prospects to something to gauge your ability, and it lets prospects find you via search.

    If you have no experience at all yet, I also suggest starting your own blog (given that you want to focus on content writing as opposed to other freelance writing specialties). Again, it’s a living portfolio piece even before you have client work to show off. There just isn’t a good reason not to do these things. If prospects don’t feel like you’re putting 100% into your own business, they have no reason to assume you’ll put 100% into theirs.

    If you absolutely insist on taking the opposite approach, your primary tactic is direct pitching. That means picking up the phone for cold calling or sending direct email pitches (but understand that both are numbers games — you’ll get a lot of “no thanks” responses for each “yes”). There’s nothing wrong with this. But again, I wouldn’t wait on a website. What if they ask for a link to your site to see your style? In this day and age, and for someone wanting to focus in this specialty area, not having a website just doesn’t make sense.

    My $.02.


  9. My most challenging thing is working smarter. I have personal, family commitments (like us all, I’m sure) that take me away from my work – unlike when I was living alone in San Diego. I’m always looking for ways to be as productive as I can be when I’m working and to be smarter about the projects I take on.

  10. I have to agree with you Cathy. Working smarter is often a challenge. I tell writers to focus on that concept all the time, and I often get one or two who contact me with the “you make it sound so easy, but I can’t really do this” lines. They can. It just takes a lot of work. I know how important it is, and I struggle with it at times too. The move. Holidays. My endless train of technical disasters last year. Things always come up, whether at work or in our personal lives. It comes down to being as productive as we can when we can, and then getting back into the swing of things as quickly as possible when distractions do happen.

    If you have any tips on working smarter, please share them (maybe start a new thread). I don’t know about others here, but I’m always looking for little ways to tweak my days to be more productive.


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