What They Do Not Tell You About Upwork

Alex Koskin
7 min readAug 11, 2020
Do you think you’re the one with the hat?

Bright and shiny image of freelance

the dream has never been closer

I’ve been there. You open a website and there is a bad and lazy article on the first page. Stupid and obvious, watery and empty. What? That guy (or girl) got paid for this crap? Outrageous!

Or you open a magazine and read an interesting and compelling material and think to yourself: hm, I could write something like this. Indeed. And you’re thinking about it more and more. And then you google “freelance writing”. And then you see free-spirited people who live their dream life. While they tackle giant issues of social injustice or moral corruption in the world. And the only thing that separates you from that noble life is a couple of gigs to build your portfolio. Oh, and the best thing: there is a platform on the mission to help people like you find people who need your services. Sign me in, you exclaim.

Unrealistic expectations

the brave new world is already here?

So many websites, have you noticed? New projects and businesses pop up every single day by hundreds of thousands. Verisign reported around 144,000 domain registrations per day in the first quarter of 2018 [1]. Sure, some of those domains will remain empty forever, some of them are placeholders. Some will be a home for annoying ads. Some will become family genealogy memorabilia. Some of them half-angry half-horny teenagers will fill with their crazy thoughts… But at least a big enough number of these websites would need professional writers to bring them to life. To fill them with clear and powerful messages, reason, and pure human thought.

Spreading human thought can be lonely. (Photo by Keegan Houser from Pexels)

The industry needs people who can weld words into sentences. And can smash phrases together to produce emotions. Who possess the rare combination of literacy and a sense of beauty and can use that talent to provoke thought and change lives. At least that’s what some of the promotional materials for creative writing courses tell you. Some of them will put a medium price that blogs, businesses, and outlets will pay you for an article somewhere between $35 and $50. And these are the more modest ones.

The picture is pretty, the bait is shiny and tasty, so hordes of aspiring writers/web designers/software developers/[fill the blank] run to the mill. And the mill eats them all.

Real hourly rates

count everything

People usually overlook “effective hourly rate”. Let’s say I work at a company and my hourly rate is $15/hour. The company doesn’t insist on the overtime, but I’m determined to work harder and longer hours to claim the proverbial ladder. The company compensates me for 40 hours per week, but I’ve worked closer to 60. That means, my effective hourly rate that week is $10/hour. So effective hourly rate can differ from the official hourly rate. It has to do with work or work-related activities that I perform outside negotiated paid time. We can argue that my commute to and from work, lunchtime, morning preparations, and voluntary/mandatory office parties are all influencing my effective hourly rate.

Super fun! See, how much fun they are having? The one on the right is sleeping, btw. (Photo by Fox from Pexels)

The same is true for freelance. Yes, you can make more in an hour than your current job pays. But all the time that you need to actually find a job can lower your effective rates. It’s not like you would spend the same 40 hours per week on actual paid work. Most likely, especially in the early stages, you’ll dedicate most of your time to landing gigs and learning how to do it better.

Time management becomes essential. Nothing fancy, log your activities in any app you like. (I use Toggle.com, the free package contains all that I need). Plan your rates. Adjust them if needed. Collect all the information to make informed decisions. As accountants and managers did at your day job. You’re one-person-business today. Govern yourself accordingly.

By the way, all the spendings (fees, paid materials, internet connection, software, subscriptions, etc.) count too. They are all part of your expenses now. You should take them into account when calculating the rates. Again, not discouraging, just warning.

Add a calculator and you have your own freelance starting kit. (Photo by Black ice from Pexels)

Starting blocks

dos and don’ts of a newborn freelancer

They don’t tell you that to find work on a platform like Upwork without previous experience on the platforms is close to impossible. Remember classic “catch 22” of conventional jobs? “You cannot find a job without experience and you cannot get experience without a job”. It’s like that but multiplied by at least 10. Job-givers do not see you. You do not have the luxury of explaining your position face-to-face. And they have an easier time to reject your application on any arbitrary reason

I call it “the castle syndrome”. When people feel protected, they behave much worse than usual. They can feel protected by a metal jacket of a fast-moving car on the highway. Or by a computer screen, big distance, and technology. Or by something else. Next time you’re in the DMV line try cut someone off and see the reaction. I bet you’ll learn some new cool nicknames and in some cases, you even risk physical confrontation. On the road, it’s a different story because the penalty is what? Some dude yelling at himself in his own car? I can live with that*.

*I do not condole rude driving in any way. The situation was exaggerated for comedic effect and in the educational purposes only.

She knows what I’m talking about. (Photo by Tim Gouw from Pexels)

So people will seem rude ignoring your proposal after the proposal. You won’t even get valuable feedback: what didn’t they like, what should you change next time. It’s like trying to beat a slot machine. When you only know the result if you’ve won. It’s frustrating especially if you have what it takes to do a job. If you have real experience in writing articles for example. That experience is good enough for you to get hundreds and thousands of reads and claps on, say, Medium. But for those kings and queens at Upwork looking to buy a 10,000 words medical research meta-analysis article for $5, no-o-o-o! But I digress.

People exaggerate the amount of available work at Upwork. In the heavenly world of Top Raters or Rising Talents, the work might be abundant and the rates might be ever-growing. But for a newcomer, it can be hard to find work. Especially since you cannot apply for every gig possible. Because of the magical concept of “connects”.

“Connects” are the way for Upwork to make money from the audience they already are making money from. Freelancers. You have only 20 “connects” after registration and you need from 2 to 6 (usually 6) connects to apply for a single gig. Then you can buy more or wait a month. Why not? You’re not here to make money and pay bills or something, right?. Oh, you have a strange strain of kids who have to eat every day? My condolences.

So you buy damn “connects”, committing a cardinal sin according to Upwork’s own Bible (Terms&Conditions): thou shall not pay to get work!

I’ve bought 20 “connects” for $3.6 ($3 + VAT), so 1 “connect” cost my 18 cents. It’s not much, I get it, but it adds up. Especially since Upwork already takes 20% off my paycheck for the gig. So to take money from me before I actually get paid… Controversial.

Big Father is watching you… (Photo by Vladislav Reshetnyak from Pexels)

The realistic approach

we’re not all doomed after all

I don’t want to discourage anyone. I want to warn and help form a healthy realistic approach towards freelance in general and platforms like Upwork in particular.

Take all the expenses into account. Know that you will need a lot of time to find work. Prepare to work for a lot less than you expect at least in the early stages. Time everything — information is power.

I see platforms like Upwork as a stepping stone in a freelance career. Many professionals and coaches agree with me on that. With the help of the platform, you can form a decent portfolio, learn to present yourself, find the best way of working, hone your hard and soft skills. For some people, some fields, or for some situations the platform can become the only source of work and income. But for, I’d say, the majority of freelancers the platform like Upwork in its current state is a crib and a playground.

It is important to keep in mind that Upwork and similar platforms are not the only way to secure gigs and find clients. Growing communities on Facebook, LinkedIn, and Telegram can do the trick. There is cold emailing, though it may sound old-school, it is a proven method to find work and spread the good word about your services. And of course, there are physical local businesses in need of good content, the right marketing, or a nice new website.

So they may tell you a lot of good things, they may paint too pretty of a picture, but hopefully, now you know better.

Wait. Is the message of this long-long read not to believe in marketing promises? Ok. Helpful. Thanks? I guess… Well, no. The message is (if you must insist on filtering the whole entirety of an article down to one sentence) that freelance is a business. Freelancer=enterpreneur. So govern yourself accordingly.

He landed his first gig on Upwork. And you can too. (Photo by Andrea Piacquadio from Pexels)

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