How to Become a Successful Freelancer on Upwork

Purchase can be hard to find, especially on the Upwork platform. Here’s my tips on how to become a successful freelancer on Upwork.

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Upwork is a contentious subject among freelancers. For every proponent of the platform, there’s three freelancers who think it’s an absolute blight. Nevertheless, I’ve earned good money as a freelance content writer on Upwork. If you’re one of the many people wondering how to become a successful freelancer on Upwork, I’d like to share some of what I’ve learned so far.

Right For Me, But Is Upwork Right For You?

Before continuing, I want to be clear about a few things. I’m not here to sell you some course on how to make money on Upwork (mostly because I don’t think you need a course for that). I’m not affiliated with Upwork in any way, other than the fact that I’m a freelancer and client who works and hires on the platform. Which is all to say that if you never touch the platform, or hate it with a passion, no worries.

This post probably isn’t for you.

Since I first joined Upwork around 2016, I’ve earned nearly $150,000 on the platform, with $65,000+ of it coming during the past 12 months. I have a 100% Job Success Score across 284 completed jobs, which has helped me achieve Top Rated Plus status. Here’s what my Upwork profile looks like:

If you're wondering how to become a successful freelancer on Upwork, start with your profile. Here's a screenshot of my Upwork profile, which indicates my Job Success Score, earnings, feedback and more.
Here’s what my Upwork profile looks like as of May 2022

7 Things I Wish I Knew When I First Started On Upwork

In short, I’ve spent a lot of time making all kinds of mistakes on Upwork. An iterative process, to say the least. If you’re just starting out, or thinking about it, here’s seven things to keep in mind, straight from my own hard-earned experience. Hopefully these insights will help you get to value faster than I did.

1. It Probably Won’t Be a Quick Buck

What in life is? There aren’t any shortcuts to ramping up a viable income stream for your freelance business, on Upwork or otherwise. It takes time to set up a complete and engaging profile. You’ll soon find that proposals play a central role in your ability to win work, as does client communication. And because Job Success Score (JSS) is a rolling composite based on a lot of different variables, you’ll need to sustain progress in order to move that particular needle.

While there’s no short cuts, you do want to take the shortest path to your first objectives. Those should be:

  1. Establish your profile
  2. Win your first contract
  3. Complete your first job successfully
  4. Get your first five-star review on your profile
  5. Earn Rising Talent status, the first of four Upwork Talent Badges

That’s not the path for everyone, but it seems to be most common. In all likelihood, you’ll spend a lot of your initial time sending out dozens upon dozens of proposals with a very low response rate. I churned through hundreds of Connects (which are required to submit proposals) before I received my first response. From there began a weeks-long schlep through a veritable shit-ton of low-end, low-pay jobs.

2. Upwork Takes a Significant Cut

Some people are unequivocally not okay with this fee. Fair enough! I can see why some people balk at paying a 20% fee when you can win clients on your own and take 100%. Hard to argue against that. I liken it to a usage tax for having access to so many job listings. And some of us need access to the job listings—we need a place to gain footing.

I certainly did when I first started on Upwork. At that time, freelancing was a side hustle. I was willing to pay the fee for such quick and expansive access to jobs on a daily basis. Plus, Upwork reduces the percentage it takes based on how much you earn with a given client. Here’s the breakdown of Upwork Freelancer Service Fees:

Earnings (per client)Fee
First 0-$50020% fee on earnings
$500.01-$10,00010% fee on earnings
$10,000+5% fee on earnings
A breakdown of the Service Fees for that you’ll have to pay as a freelancer on Upwork

To give you an idea of what this looks like in practice, let’s take one of my oldest clients on the platform. In the past three years (May 2019–May 2022), I’ve paid $3,389.01 in fees against $58,374 in earnings. Here’s what that looks like on my Upwork dashboard:

An example of Upwork Fees that I paid for one of my long-term clients
An example of Upwork Fees that I paid for one of my long-term clients

3. There’s Bad Listings, Flaky People, and Scams

Yes, there are plenty of ill-defined, low-paying jobs to wade through. There are plenty of flaky, oddball, cheap-o clients, too. Get a load of this “Additional Message from Client” that I received in response to one of my proposals:

Example of an actual rejection I received in response to one of my Upwork proposals
Example of an actual rejection I received on one of my proposals. Guess I’m not a good writer!

There’s all kinds of clients on Upwork and they’re not all reliable. For example, I’ve had multiple clients go radio-silent after I delivered my first draft. No feedback. No formal close to the contract. Just gone without recompense. Since then, I’ve learned to never proceed with work unless I receive not only a job offer, but a funded and active milestone. That way, I’m covered under the Upwork Payment Protection guidelines and will likely be paid even if a client ghosts me.

Warning signs of a bad Upwork client

  • Job listing/invitation includes typos
  • Asks to communicate via text/WhatsApp/Skype/Telegram
  • Doesn’t have a profile photo or work history
  • Has poor ratings from other freelancers
  • Asks for free work in exchange for exposure
  • Asks for free “trial” work
  • Asks you to buy a product in order to do the job
  • Wants something unethical (writing another student’s paper for them, for example)
  • Hunting for a bargain
  • Acts like a jackass

One more thing. I see a lot of people on forums, communities, and social media screenshotting all of the laughably bad jobs they come across on Upwork. That’s their prerogative. All I can say is it takes far less time to ignore a post, or decline a job invite, and move on to the next opportunity.

4. Confident Communication and Pricing Will Reduce Problems

You’ll mostly interact with clients through the built-in messaging feature, which now includes the ability to conduct calls and video chats, or record Loom videos. Take it from me: you can avoid so many problems if you communicate and price your projects with confidence.

Think about it: a lot of clients have never hired on Upwork, hired for your specific services, or both. Beyond your actual skill (writing, graphic design, etc.), learn how to guide prospective clients through a project. What steps will you take? What will the project timeline look like? And what is your fee? Have your answers ready, because they’ll come up during your initial communications.

The quality of your answers might win you the job.

This means asking the right questions of the client, too. 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.

Lastly, a note on pricing. I always bid on Upwork projects based on my rates, no matter what the client lists as their project price. If they want to pay my rate, wonderful—we’ll be on the same page and I’ll be fairly compensated for all the “stuff” that goes into that website copy, blog post, or case study. If not, I consider it a bullet dodged, politely decline, and move on.

5. Your Upwork Profile is Very Important

I’m active on the Upwork Professional Group on LinkedIn. Almost daily, someone asks why they’re not seeing any traction. The first thing I do is look at their profile. Nearly 100% of the time, those struggling freelancers have incomplete, poorly written, or thin Upwork profiles.

Similar to LinkedIn, Upwork runs on an algorithm. That algorithm figures out how to rank freelancers’ profiles and job listings for the many people searching Upwork every day. As a freelancer, much of your algorithmic juice comes from your profile. And you want a lot of algorithmic juice, because it’s crowded out there! Here’s what it looks like on my end when I search Upwork for a freelancer:

A screenshot of an example freelancer search that I conducted using my Upwork Client profile
A screenshot of an example freelancer search that I conducted using my Upwork Client profile

This is just one of many different ways that Upwork displays and ranks profiles across the platform. If you want to get hired, your profile needs to start ranking for these searches. So, first and foremost, make sure your Upwork profile settings are as complete as possible, including:

  • Profile picture
  • Name, location, time zone, availability
  • Visibility
  • Custom profile URL (if available)
  • Project preference
  • Earnings privacy
  • Experience level
  • Categories
  • Specialized profiles
  • Linked accounts

Then there’s some of the other options that comprise the actual meat and potatoes of your profile.

  • A strong title
  • Rate
  • Video overview
  • Written overview
  • Work history
  • Hours per week
  • Language(s)
  • Education
  • Verifications
  • Portfolio
  • Skills
  • Project catalog
  • Testimonials
  • Certifications
  • Employment history
  • Other experiences

It’s a lot, I know. But do yourself a favor and devote time to each and every one of these items. This is the #1 mistake I see from new freelancers on the platform. Oh, and I have an extra little secret tip for you: as you accumulate completed jobs, you can link portfolio items to those completed jobs. Then when a client is looking at your work history for a particular job, they’ll also see the work you delivered.

Here’s an example from my own profile:

A screenshot of completed Upwork jobs for which I linked related portfolio items—a neat little trick to spruce up your profile
A screenshot of completed Upwork jobs for which I linked portfolio items

6. Poor Feedback Will Cost You

JSS is a big deal. As you complete jobs, this score changes based on metrics like client feedback, jobs completed vs. jobs abandoned, etc. The idea is to keep this number above 90%, as it appears prominently on your profile. What’s more, your JSS and client approval rating shine big and bright (or dark and ominous) on your Upwork profile. Clients can filter their searches based on JSS thresholds. Cancelled jobs, negative feedback, poor ratings, or jobs with no ratings can all degrade your JSS.

As you can see, I’m not immune:

An example of a poor job feedback from some the older jobs on my Upwork profile
Bad feedback from some old jobs on my Upwork profile

If you take exception with the way Upwork weighs client feedback, I feel you. The onus falls heavily on the freelancers. For example, I was a Top Rated freelancer with a 94% JSS when my score unexpectedly dipped below 90%. Business flagged and I had trouble winning clients.

My eyelid started twitching.

On face value, my Upwork profile was in order. No bad feedback. Nothing I could point to that created the spike. When I followed up with Upwork support, they threw their hands up. What I later found out is that clients leave both public and private feedback at the close of a job. The client can smile to your face and leave bad private feedback, which ultimately hurts your JSS.

Yes, you can dispute bad jobs. If the dispute is valid, Upwork will review it and in some cases make things right. But they won’t adjust profile ratings and they’ll do little to help freelancers recover from a dip in their JSS. The client, unless Upwork is its only source of freelance work, are none the worse for wear. They can just dip out and find their freelance work elsewhere.

This was probably the closest I came to turning in my card and joining the others howling scam on LinkedIn and Twitter. Instead, I got back on my chestnut and slowly rebuilt my score. I did the very same thing I would do to recover from a bad client experience out in non-Upworklandia.

7. You Can and Should Skim Strategy from Successful Upworkers

Throughout this post, I’ve included screenshots to and links to my actual profile. I’ve shared the exact tips and lessons I learned on my path to Top Rated Plus status. My advice? Emulate all of it. That’s what I did! Am I saying you should copy titles and descriptions? Hell no! I’m saying go take a look at what other successful Upworkers are up to and apply those lessons to your own journey.

You’re going to find a million and one people writing and promoting their gated ebooks and paid courses about “how to write better Upwork proposals” and “how to make a gazillion dollars a month on Upwork.” Some of it’s worthwhile, some of it is not. In my opinion, you don’t need to pay for any kind of course. You just need to learn Upwork best practices, commit time to your profile, and continue iterating on your process.

Valuable Free Upwork Resources for Beginners

Here are some of the free resources that I’ve used to be successful on Upwork:

Finally, just go peruse profiles around Upwork. I promise you’ll learn something from your fellow freelancers.

Bonus! One Underrated Lighthouse, One Practical Shortcut

You don’t need to send fifty proposals a day forever. Once you’re established on Upwork, something brilliant starts happening. Job invitations come to you. Many of these are invite-only, meaning the client isn’t making the job public and inviting dozens of proposals. They’ve already shortlisted you.

When you start to consistently receive quality invitations to apply for jobs, take that as a strong indicator that you’re on the right track. I haven’t searched for a job on Upwork in at least a year—I leave my profile active, let invites come to me, and pick and choose which I’d like to respond to.

That’s the lighthouse. Now for my shortcut, which is pretty simple: connect with people who are already on Upwork. Could be a friend or family member. It might be a fellow freelancer in your social media network. You’re looking for someone who might be willing to hire you for those initial jobs directly.

This is a great way to establish yourself without having to go through the upfront drudgery that crushes to many beginners on Upwork. If you want a better idea of what this looks like, I detailed the entire process in the following blog post:

Closing Thought: Upwork is Just Another Iron in the Fire

Hopefully, my explanation and strategies provide a little more context to the Upwork conversation. If not, that’s okay, too: I will continue using and profiting from the Upwork platform, either way. And you should too, if that’s your prerogative. For me, Upwork was my foot in the door. It was how I found my first paying gigs.

But it’s only one iron in the fire. Beyond Upwork, my business pipeline has expanded to include referrals, leads from social media, and organic website inquiries. As much success as I’ve found on this platform, I wouldn’t recommend relying on Upwork as your sole source of freelance income.

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