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.
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!
Stuart Danker 
I’d love to hear your thoughts!