The Dangers of Freelance Marketplaces (like Upwork) No One Talks About

Upwork and other freelance marketplaces exploit writers
Photo by Vlada Karpovich from Pexels

While AK’s anniversary isn’t until April, February marks another milestone – one I haven’t discussed in the past. Namely, the moment I decided to pursue my long-time (life-long) dream of writing. I started sitting down with books on freelance writing, researching sole proprietorships, and looking into freelance marketplaces. Why? Well, because everyone suggested the virtual job boards as the best place to kick off a freelance career. And one that kept showing up? Upwork.

I celebrate the anniversary as the day I scored my first contract. But Antihero Kreative entered the Upwork job boards in March – sealing an uncertain fate I haven’t disclosed here. Until now.

Freelance Marketplaces

If you’re not yet a freelancer, you may only recognize the names of the freelance marketplaces drifting around the internet these days:

  • 99designs
  • Fiverr
  • FlexJobs
  • Freelancer
  • Guru
  • People Per Hour
  • Toptal
  • Upwork

(No, I’m NOT going to link out to these cesspools. Besides, tech-savvy individuals can find them without my assistance)

Freelance marketplaces are a combination of a job board and a cattle auction. Scope one out, and you WILL find advertisements by clients for everything from graphic design to writers to website design (and anything else you can think of). Filters allow you to search through subject matter – and you’ll find something there for everyone, too – project type, deadline, and budget. It SOUNDS like Shangri-la for the freelancer. And when you’re contemplating breaking free from the bounds of a traditional 9-5 job, it’s difficult to resist. (Or, you know, supplementing your current income)

However, EVERYONE registered on the marketplace gets access to the boards. And those clients? They range from “average” people up to legitimate companies. This is where the cattle auction comes in – in REVERSE.

And that’s the part NO ONE talks about when they encourage you to sign up with one of these sites.

So let’s start.

Upwork: The Dark Side

You’ve probably already guessed where the slippery slope of Upwork, Fiverr, and the rest lead. But personal anecdotes resonate best. So allow me to conduct you through my experience. (And you can judge for yourself whether you feel that registration is worth it)

I hit those job boards with a heaping mountain of innocence and naivete. Armed with my research and reading, I held quality and writing talent as KING. After all, why would anyone in their right mind pay a registration fee to advertise on Upwork if they weren’t looking for THE BEST writing?


Clients, having spent those fees, DON’T want to spend any more. So quality doesn’t matter. They’re looking for the freelance writer with the LOWEST bid, willing to deliver the FASTEST. Period.

The time I spent writing individual pitches? My careful hours drafting dummy blog posts to have writing samples? Wasted.

As Carol Tice at the Freelance Writers Den puts it (so eloquently), these content mills center around “Race to the bottom” pricing. (Hence my reverse auction analogy) You can have stellar writing skills, meet deadlines every time, and have the most pleasant working nature. But if you dare to set a project bid too high, no one’s going to touch you.

The client’s king at Upwork – not the writer. And they KNOW it. This leads to other misbehavior:

  • Late payments
  • Abusive dialogue
  • Employee mentality (you are NOT a partner!)

Hitting You Where it Hurts

Then there’s the ultimate sneak attack that somehow slips the mind of all those Upwork “Gurus” preaching its wonders: the FEES.

Clients pay to post their ads. They also lose a percentage of each project (another reason they turn stingy) to Upwork.

And the same applies to YOU!

Every pitch costs you “tokens.” Free accounts only receive a handful a month – enough to pitch a handful of times. (It depends on the client. Some set their cost low, others high) You can pay a monthly subscription to gain more, of course – filling the marketplace’s coffers. I’m here to tell you NOT to do that (and I’ll explain why in a minute)

But the fund hemorrhage doesn’t stop there. Upwork skims a percentage from EVERY SINGLE PAYCHECK YOU COLLECT. The longer you work for a client, the lower the percent drops, but it won’t disappear. And if your client’s a newbie to the site and sends a new project? Your percentage starts over. (Surprise!)

And if you try to bid to account for that loss? You got it – odds are you’ll lose the pitch.

Gaming the Upwork System

Did I get my start on freelance marketplaces? Yes. So can I hear you screaming foul from the back row? Of course.

But given a chance to start over, I wouldn’t repeat my mistake.

Unfortunately, Fiverr, Upwork, and the rest of the crew are here to stay. People tout them as the Holy Grail – not the Death Star. And while it makes me twitch when I see those recommendations – and dive in to protest – I recognize I’m fighting Godzilla with a straw.

So I’m going to tell you how to work from inside the system. Until you can get OUT.

(And you need to escape ASAP)

Yes, I built my portfolio in Upwork. I also did so WITHOUT paying for a monthly subscription – within 3 months. No, you can’t get away with a handful of tokens in the beginning. Clients are assholes. They deliberately set the cost of their post to eliminate newbies. And landing those first jobs?

It’s a game of numbers.

So grit your teeth and subscribe – at the LOWEST option. (Trust me on this one)

Commit to as much time scouring the job boards as your schedule will allow. And send out pitches. ANYTHING you feel comfortable handling, send the pitch. DON’T undersell yourself, though. You have talent! You’re a phenomenal writer – price yourself reasonably. (Pricing guides are a Google search away. Or use Writer’s Market like I did) Clients will start to bite. You’ll begin building clips. And within those few months, you’ll get your crucial ranking.

As soon as you have Top Ranking? Cancel your subscription. You won’t need it anymore. (I promise) People parade that stupid status as if it’s difficult to attain. It’s not. Complete projects and satisfy your clients, and you’ll get there.

More importantly, it puts you on Upwork’s internal search engine. So they start coming to YOU with job posts. And responding? FREE. Enough of those, and your token account turns into unused savings. When I deleted my account, I had over 250.

Building a Portfolio Base

Find out where your work’s going. If a client won’t share (happens all. The. Time.), use the Wayback Machine to hunt for your unique phrasing. You can then use Full Page Screenshot to generate a PDF to display in your portfolio.

And don’t let someone bully you. If you don’t sign a non-disclosure agreement (NDA) – something that NEVER happened the entire time I was on Upwork – you ARE entitled to reference your work!

Ghostwriting does NOT mean you have zero rights to the piece! (Clients LOVE to tell you that) All it means is your name doesn’t appear in the byline. There are famous ghostwriters out there. It’s a skill to match someone’s voice, tone, and style. Flaunt it!

At the same time, build your writer’s website. Polish your profile on LinkedIn. And join a REAL writing community. Then you have the tools to break free.

Mission (Not) Impossible

Yes, I took the road NO ONE should travel. Did starting on Upwork ultimately pay off?


And no.

I endured some pretty miserable experiences. Things I don’t wish on anyone who wants to tackle freelance writing (or any freelance job, for that matter). Did I also get to meet and work with fantastic clients? Of course.

But it’s a crapshoot with these marketplaces.

And Gambler’s Ruin predicts you lose more than you win.

Do yourself a favor: stick to writing communities designed to HELP you. Not marketplaces designed to fleece you.

And if you have an experience you want to share with Upwork, Fiverr, or one of the others, leave a comment below!

Author: Andria Kennedy

I speak the thoughts rattling around in my brain, sharing topics I think other people want and should hear (or are afraid to talk about themselves). I bring my personality and quirky state of mind to everything I write; serious topics shouldn't be devoid of humor. That includes my blog and freelance work (part of my charm). I've been writing for as long as I can remember. It's a source of solace and enjoyment for me. I'm lucky enough to call what I love my career - so it's NOT work! I live in Virginia with the Minions (four cats and a Greyhound) and my wonderful husband, who ensures I stay fed - no cereal for dinner - and as close to sane as I can get.

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