How to Win Your First Contracts on Upwork

Purchase can be hard to find, especially on the Upwork platform. Here’s how to navigate those early choppy waters and begin winning business as a copywriter.

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Upwork is a contentious subject among freelancers. Some argue that Upwork is a good side hustle; others think it is a cancer to freelancing as we know it. Still, I’ve managed to earn good money for writing jobs on Upwork, despite some of the curmudgeonly commentary I’ve read to the contrary.

I’d like to share what I’ve learned so far.

Know it won’t be a quick buck

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.

Be prepared for Upwork to take a cut

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. Plus, Upwork reduces the percentage it takes based on how much you earn with a given client. For the first $500: 20% for the first $500. For anything between $500 and $10,000: 10%. Anything over $10,000, and that percentage goes down to 5%.

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, cheap-o 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, it’s not ideal, and it’s the freelancer that is ultimately penalized, even when it’s the client that skips town.

There are scammers and lemons, too

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 can be 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 Upworkers

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. 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 will come in time

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.

Hustle, because it’s ultimately up to you

Not terribly different from the real world. How to make money on Upwork is how to make money as a freelancer, certain caveats notwithstanding.

  • 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 have a start right and proper.

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