Upwork tends to be a contentious subject among freelancers. Just look at the comments I received on the LinkedIn question I posted. Some argue it’s good on the side; others think it’s a cancer to freelancing as we know it. Still, during my first couple of months as a member, I’ve managed to earn money for copywriting jobs, despite some of the curmudgeonly commentary I’ve read to the contrary.

For the skeptics:

Image of Upwork Job Success Score

Peanuts? Maybe. But I have my purposes and goals that I continue to push toward, income-related and otherwise. Regardless, I’d like to share what I’ve picked up during my first few months using Upwork.

Ransack this list. Steal my ideas if they’ll help you get paid for your writing. Better yet: let the rest of us know what you know—good, bad, or otherwise. The more informed, quality writers winning contracts the better.

It’s not going to be a quick buck

But what in life is? It takes time to set up a viable profile and proposal strategy, earn your first contracts, and get positive client feedback on your profile. I had to take a few lower-end jobs at first to break through, had to fail a handful of times before succeeding. Since then, I’ve steadily won work and managed to raise my rates twice. My advice? Toe the line a bit. You don’t have to work for free, but keep in mind that it takes a while to gain traction.

Upwork takes 20%

And if they find out you’re being paid for Upwork work outside of Upwork, say good bye. That’s a violation of the Terms of Service. As far as the cut goes, well, I suppose it’s the usage tax for having access to so many job listings. Some say it’s a gouge (why take a 20% cut when you can win clients on your own and take 100%?), which is hard to argue against. Still, some of us need access to the job listings—we need a place to gain footing.

Some jobs are crap, some clients are flakes

Yes, there are plenty of ill-defined, low-paying jobs to wade through. And there are plenty of flaky, oddball clients. For example, I’ve had two clients go radio-silent after I delivered my first draft. No feedback. No formal close to the contract. Luckily, the milestones were funded, so I ended up getting paid). Still, not ideal.

Keep an eye out for scammers and lemons

Some warning sings:

  • Sketchy communication
  • No profile photo
  • No work history
  • Requesting free work
  • Requesting communication and payment outside the Upwork platform
  • Asking you to buy a product in order to do the job
  • Unethical projects (writing another student’s paper for them)

Client communication is a moving target

At least good communication is. Much of my interaction with clients has been through the built-in messaging feature (though I have had a few calls), and a lot of it has been quite good. Still, some clients are in different time zones, or have a different first tongue, which can make things difficult. Other times, clients are sloppy, unprofessional, or downright rude. I’ve learned to cut ties with those clients.

But you have to be careful …

Failed contracts can cost you

Your Job Success Score and client approval rating shine big and bright (or dark and ominous) on your Upwork profile. Your profile is how clients decide to hire you (or invite you to interview for a job). Cancelled jobs, negative feedback—these can take time to cycle out, and might be red flags to potential clients.

Be explicit about expectations from the outset

This means asking the right questions. What format is the deliverable? When do you expect to see the next draft? Get all the information you need so that there are no surprises. Gonna miss a deadline? Not good practice, but you need to communicate this to the client.

Establish funded milestones

You must insist on funded milestone so you don’t get burned (that is, to prevent clients from running off without paying you). If you are going to take an hourly contract, check the client’s work history for feedback that might clue you in on a lemon. Luckily, Upwork has some built in protections to prevent this kind of thing, but disputes still happen.

Skim strategy from established tipsterss

Tipsters are writing and promoting their “how I plan to make 100k my first year on Upwork” content all over the web, and some of it is worthwhile (Danny Margulies comes to mind). I borrow many strategies from this kind of content, still do. Keep in mind: some of these folks are funneling you into paid courses that teach you how to make money on Upwork. I’m not going that route, know little about the courses. I followed the freely available tips and it got me on my feet just fine.

Invitations do come

As you build your profile and work history, you’ll begin to show up in search and receive invitations to apply for jobs. This is good—it means a client thinks you might be a good fit for their job, and that you’re getting noticed in search results. In my experience, some job invitations have led to good paying work, while others have been junk, scammy, or unsuitable.

Leverage the community

The Upwork forum is full of seasoned users and moderators asking and answering the same questions you have. Check there first! It’s a living, breathing knowledge base and, chances are, your question has already been asked (and answered).

That goes for proposals and profiles, too

Every blog about making money writing on Upwork has a section on writing winning proposals and killer profiles. There’s also a dedicated thread on the forums for newcomers, which you should probably check out.

Here’s my profile, for reference.

Image of Martin Ceisel Upwork profile

Prone to downtime

Yeah. More than expected. From time to time, parts of the Upwork website will go down completely, preventing users from logging hours or communicating with clients. You can check the status of the website here: https://status.upwork.com/.


@UpworkHelp is the fastest way to receive support from the Upwork team, in my experience (I’ve opened multiple tickets this way). Here is one of my recent interactions, which was followed by an email from the support team.

So, it’s not terribly different from the real world. Don’t be a knucklehead. Communicate well. Be prepared for The Man to skim off the top. Keep multiple irons in the fire. And stand up for yourself. For a some additional tips from both the freelancer and client perspective, check out this Upwork review.

Keep these things in mind and you should be just fine.


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