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

Man working on laptop

Photo: Austin Distel

Freelance writing is the dream, isn’t it?

If you’re anything like me, you’ve probably fantasised about combining your wordsmithery with the nomad lifestyle. What an image that’d be, occasionally taking your eyes off the mountainous horizon of Costa Rica to reply to a work e-mail, one that’d celebrate your great work and promise your payment before the day’s end.

Of course, some of you would know that nothing could be further from the truth. In fact, you’d consider yourself lucky to even hear the word ‘payment’ mentioned more than once throughout your relationship with a client.

Still, it does well to dream, and there are people enjoying the freelance writing life. It’s just that getting there isn’t as fun as it seems.

So, what challenges lie between you and a freelance-writing life? Join me as we explore the less-savoury flavours you’ll find in that box of chocolates.

Negoti-hate

As a writer, you probably have a tendency to want to be alone. A blanket statement, I know, but there must be a reason why you burying your nose in a book, am I right?

So if you’d rather have your KPI measured by work output instead of how popular you are, then you’ll probably balk at one of the most important skills to have in your freelance-writing venture, and that’s negotiation.

Contrary to popular belief, you won’t get clients knocking on your door and offering you work at the standard market rate. I’ve been writing for a living for nine years, and I still don’t get the twelve-cents-per-word (Malaysian rates) during first contact.

This is because the craft itself is seldom appreciated, especially if your prospective boss doesn’t have a finger on that pulse.

To them, it’s all the same as long as there are words on the screen. You’d think they’re shopping for cleaning products instead of a creative service, judging by the way they approach hiring.

The onus is on you, then, to justify your worth. Are you going to do that through pure negotiating grit? Or would it be through your kick-ass portfolio?

Either way, you’re the one who’s going to have to command decent terms for yourself, especially when it comes to securing advance payment and the like. And speaking of that…

New phone who dis

The golden standard of advance payment is to receive 50% upfront and the rest when you’re done. Or you could operate by trust of the invoice and risk doing months of work, only to have your clients come up with another excuse to why your payment is late, or why it isn’t there at all.

Weirdly enough, it’s the larger companies that take their time paying up. Oh yeah, and if you’ve tried hassling your clients to pay up when COVID first hit, then you know just how nerve-wracking it can be to have to beg for what’s yours in the first place.

Still, the most frustrating thing is when your clients ghost you so quick you’d think you were on a Tinder date. And don’t think that it’s the just first-time clients who’d do this to you either.

I think we’ve established that us writers hate dealing with people. So you want to be a freelance writer? You might end up hating people even more.

Woman hiding behind leaves

I SEE YOU DAMMIT NOW WHERE’S MY MONEY! Photo: Sharon Mccutcheon

Lifelong learning

I bet you’ve heard this more than a million times before, but learning doesn’t stop at high school. In fact, some might argue that life offers far more valuable lessons than the average academic institution.

Sure, lifelong learning is necessary, and sometimes easy, but that’s only if you enjoy the topic at hand.

For instance, I can read books I hate just for the sake of learning, and I can spend hours doing nothing but writing drills. But sit me down in a social-media ads seminar and you’ll see my eyes glaze over. If you look carefully, you might even see my soul bouncing off the walls as it tries to leave the building.

But that’s the reality of the job. It’s not enough to just be a writer anymore. You’ll need to learn about everything else that you didn’t sign up for, such as SEO, marketing, and even—gasp—networking.

“What?” you might be asking. “I need to learn to network as a writer?”

Well yes, my internet friend. And that brings me to my final point.

Hello, is it me you’re looking for?

This is perhaps the worst part of freelance writing—at least to me—as it involves scrounging for writing opportunities while trying to stay off sites like Fiverr and Upwork.

The good news is that most writers tend to get jobs through word of mouth, so internet browsing can be kept to a minimum.

The bad news? You’ll have to learn how to schmooze, to put yourself out there, so that when a friend of a friend needs a writer for their website revamp, they’ll know who to recommend.

Not a fun prospect for us writers—okay maybe I’m projecting my own insecurities at this rate—seeing as to how we’d rather not deal with people, but anecdotal data has proven that some of my biggest gigs have indeed come from referrals.

All my jobs over USD 1,000 were recommended through friends or old bosses, because let’s face it, nobody’s going to throw that kind of money on just another random freelance writer. So yes, while your skills do matter, knowing the right people does does matter too, sometimes even more.

Are you going to take the leap?

No matter what I say, some of you might still be holding onto your aspirations of being a freelance writer. And for those of you who are unsure if you can realise those dreams, I’m here to tell you that you can.

Why? Because I had six years worth of hairdressing experience (read: nothing relevant) before I started writing for a living. Also, I’m from Malaysia, where the chances of selling words for a living are even lower than in developed nations. Heck, I didn’t even finish high school. And if someone like me can do it, so can you.

Need more practical advice? Then start with a full-time writing job. Be a content writer, a junior copywriter, or even a social media admin.

I myself started off in a publishing house that produced pullouts for the national newspapers. While the exposure was good, the contacts I’d made proved to be even more important, as I’d get all my subsequent opportunities through these contacts in one way or the other.

It’s never too late to do it too. I was almost thirty when I took up that entry-level post. And now that I’m here, I’ll never hesitate to start over in a different field if that’s where my calling lies.

Because no matter what we think of our circumstances, we do live in a time where it’s possible to pursue our dreams thanks to the power of the internet. And that, ladies and gentlemen, is the true dream.


I made an Instagram post that builds on this story, so if you liked what you read, do make sure to check it out!

64 thoughts on “Do You Have What It Takes To Be A Freelance Writer?

  1. Great post and so true. I’ve worked with many sites and magazines over the years with experiences allover the spectrum. It’s funny because I just wrote a post talking about promoting freelance work. Keep up the great work!

    • Lol what a coincidence. Yeah, the experiences really do differ, and it’s sad that the best clients don’t usually offer a steady stream of jobs, because that’d be the dream. Thanks so much for stopping by, Brad!

  2. Negoti-hate might be my new favorite word.
    I really needed to read your last two paragraphs. I’m tired of working in my industry, but loathe the idea of being an entry-level beginner in something else in my mid-thirties. But maybe that is just what I need to do.

    • Entry-level is my jam, as I’ve been doing it numerous times (am actually going through another one right now as I explore teaching), and I can safely say that it’s really not as bad as most people think it is.

      Like, you don’t lose your ‘upgrades’ per se, and have much more to offer than the standard writer, thanks to your previous experience. Wishing you the best!

      • That’s so funny. I’m eager to leave teaching after 17 years and would love to write/copyedit. I’ve taken steps to learn the ins and outs of copyediting, but all the ick-tastic things you mentioned for freelance writers pretty much apply to freelance copyeditors, as far as I can tell.

  3. I earned a certificate in copywriting but did nothing with it (another one of my famous wastes of money). I didn’t see any jobs that didn’t require years of experience and a fat portfolio. Plus I am afraid of talking to people. So there went that plan.

    • You don’t need a real portfolio to get started though. You can just write a few pieces that emulate the format of your favourite publications, and that’s usually enough for an employer to judge if they’d like to work with you or not. Don’t disqualify yourself before others do! You’re way more talented that most of the ‘real’ writers I see out there. Hope you pursue it if your interest is still there.

  4. Having been a full-time freelance writer for just two years, I can reliably say that ghosting HURTS! You pour your energy and talent on a long article only for the client to stop emailing you. What’s worse is that they will contact you again months later offering something new as if no payment is pending! The NERVE!

    So, wanted to thank you for this piece that allowed me to vent. Just a little. Keep up the great output. :)

    • Lol oh yeah. Also on that list are fussy clients who seem to hate your every work, but then end up calling you up for another job. It’s a weird world, really. Thanks so much for sharing your experience, Cecilia!

  5. Pingback: Do You Have What It Takes To Be A Freelance Writer? – Kreativ Solo

    • Constant anxiety every time it’s my turn and a customer walks in (especially if they look like they’d fuss over every strand). Other than that, I’d like to think that my charms have gotten me through what would be a very ‘frontliner’ kinda job.

      That’s a great question. Thanks so much for asking it!

      • That’s hilarious. As an introvert, I always dread going to the hairdresser. It’s just chat, chat, chat for 45 minutes. As a hater of small talk, it was pretty much torture. Thankfully, since the pandemic hit, I’ve been having my totally unqualified husband cut my (medium length, curly) hair. I’m sure a true professional would balk at the results, but I’m ok with it and I don’t have to make small talk!

      • Lol, I think I picked up on that during my time behind the chair, and as a fellow introvert, I too have appreciated some of my quieter clients who’d enjoy the mutual rest we’d give each other through silence. Thanks for this comment, fellow introvert!

  6. Making the right connections is so important!
    Thanks for this! I’ll keep this for a time when I consider really doing freelance writing.

    I just don’t like dealing with people 😂

  7. Wow this is such an inspiring post! I think a lot of writers have to deal with their own self-doubt and fear of failure.. I know I sure went through that! Thanks for the inspiration!

    • I guess it never goes away for writers, no matter what they achieve in their career. But that’s a good thing maybe, because it helps them strive harder than they usually would. Thanks for taking the time to comment!

  8. Wow, this was so helpful! Thanks for taking your taking your time to write this! I can really tell you care, and want to help others to not only achieve their dreams, but get what they’re putting themselves into! Hope you have an amazing day :3

    • Yeah, I’ve waited for almost a year with two different global companies. The small businesses? They bank in my money once the job’s done. Maybe it’s different for others. Anyway, thanks for stopping by again!

    • I know, right? Even if I were to chase my dreams of being a writer for a game studio (say, for games like Fallout, Cyberpunk, or Baldur’s Gate), I’m sure that there’ll be the undesirables there as well.

      But whatcha gonna do, eh? Part and parcel of life. Thanks for stopping by as usual, Jim!

  9. Yep, writing–freelance or not–is work, and not just with words. It can be really intimidating at times seeing how much interpersonal work is involved in writing. Still, if you also glaze over in social media ads seminars, that give me hope!

    Oh, I also wanted to let you know that I nominated you for a Vincent Ehindero Blog Award. I’m not sure if you do award posts, so no pressure. I just really enjoy your writing and I wanted to show it with a nomination!

    • Am super honoured that you nominated me! I’m always thankful to see your name in the comments section, Ceridwen (I understand this is your pen name).

      Also, regarding interpersonal relationships in writing, I’m going to share Bill Burr’s story when he complained about his mentor about having to learn to schmooze and network as a comedian, and after listening to him, his mentor finally said: “Then get good at schmoozing.” That was it. No sympathies, no further advice, just “Get good at it.”

      I guess that’s what we’re looking at as well, lol. Oh well.

      Anyway, thanks again for your wonderful comment and nomination!

      • I’m glad to have found your blog! I always end up smiling as I read. 😊

        Ha, that is a great story! Honestly, that kind of practical kick is exactly what we need sometimes. I’ve had many times when I wanted sympathy and got something sterner that pushed me to step outside my comfort zone. And I’m thankful, at least in hindsight!

  10. Thank you for sharing your thoughts here. These are good thoughts/reminders for those of us who are sitting here contemplating such. Interesting as I read, I am thinking “yes, I knew that” or “Oh, wow, yeah, good to know.” or “I’d forgotten about that”. Thanks for the introspection – good for the soul.. and pocketbook.

      • I like exercise and eating healthy. I even love talking to folks and making friends. It’s the ‘networking’ for gain, that’s hard in multiple ways.

    • Indeed. We don’t realise just how much time we have, with all the social media browsing we do today, but ever since I committed to writing at least a little bit every day, I’ve begun to realise just how much time we can make for ourselves if we only strive to do so.

      Lately I’ve been helping a company with day-to-evening classes and I’ve found that lunch time is a good time to write. Thanks for stopping by!

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  12. ‘you probably have a tendency to want to be alone’ but you must network to get your best clients. So true. Its your tone of writing and addressing our fears that makes me feel that you understand what I am going through. Sales and self-promotions have to be done till we get out 20 testimonials. Next item to be wary of is ‘where is my money’: as an individual freelancer it may be difficult to follow up and get our due wages. The 3rd point of lifelong learning also resonates with me: but here we must do both learning and writing side by side. Learn-do-teach is the process to follow. Thanks for highlighting these important aspects of freelance writing.

    • You have no idea how happy it makes me feel to have someone tell me that my writing resonates with them, because sometimes, that’s all I ever want to do with my writing, really.

      Thank you for taking the time to read and drop this meaningful comment!

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