Pros and Cons of Upwork 2022: An analysis from a $500k freelancer

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As someone who has earned over $500,000 on the Upwork platform (and is on pace to hit $600,000 in 2022), I’m often asked about the pros and cons of Upwork.

Read Also: Can you make good money on Upwork? How I made $500,000 in 4 years

Upwork, for the uninitiated, is the world’s largest freelancer marketplace. 

On the site, freelancers can browse jobs posted by prospective clients from all over the world. 

Clients love Upwork because it allows them to shop for talent outside of their immediate area, in any niche imaginable. 

Freelancers love it because it takes the dreaded “cold-pitch” out of the equation. Upwork clients are already willing and ready to hire. 

It’s a bit like fishing in a pond where you know the fish are biting.

The platform’s most well-known competitors, who you may already be familiar with, include and Fiverr.

However, as you might imagine, Upwork is far from perfect.

Just like any business, there are pros and cons. 

If you’re wondering whether or not those pros outweigh the cons, you’re in luck. 

Below, I have compiled a list of Upwork’s biggest pros and cons to help you make the decision for yourself on whether or not Upwork is worth the hassle.

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Upwork Pros:

1. It’s easy to find jobs and paying clients

Every new freelancer has asked themselves the same question at some point: Where do I find clients? And it’s probably safe to say that most freelancers have also experienced how difficult finding quality clients can be.

Cold calls and cold emails require a ton of time with little payoff.

The same can be said for social media. 

And it’s next to impossible to score word-of-mouth referrals when your work history is limited.

Finding jobs specifically catered to your specific skillset on Upwork, in most cases, is a breeze. Especially for the following popular freelance fields:

  • Graphic design
  • Machine learning
  • Data analytics
  • Mobile development
  • Video production
  • Search engine optimization (SEO)
  • Web development
  • Writing

Dozens of new jobs are posted to the site every minute of every day by clients who are ready to hire.

You don’t have to convince them that they need the service. They already know they need a skilled professional who can do the job. You just have to convince them that you are that skilled professional.

And while that may sound easier said than done, with a bit of practice and preparation, sending winning proposals and landing jobs can be a breeze.

Read Also: How to write an Upwork proposal: 11 proven tips with samples

It’s a bit like shooting fish in a barrel.

2. Upwork handles the contract, billing, invoicing and mediation

Another problem that frequently plagues the freelance community is the subject of how to handle contracts, billing, invoicing and mediation (in the unfortunate event something goes wrong). 

These tasks can be especially daunting for new freelancers. And expensive.

Using myself as an example, when I am not freelancing on the Upwork platform, I pay Fiverr Workspace $216 per year to handle my invoicing and payments. I pay Rocket Lawyer $399 per year to handle my contracts and I incur fees from payment processors like Paypal and Stripe. Not to mention the fact that there’s still a lot of manual work involved even with the help of these platforms. 

Read Also: Best tools for freelancers 2022: 14 essential resources for your business

And heaven forbid there’s ever a payment or contract dispute. I’d have to file my own claims and hire my own legal counsel. 

It can be a scary world out there when you are on your own.

This is why, in my mind, one of Upwork’s greatest “pros” is the often looked-over fact that they handle all of those backend operations for you.

Your Upwork proposals (as well as messages sent through the Upwork messenger) essentially serve as your contract.

Upwork also helps handle payment collection and bank deposits. 

And should a dispute with your client arise, Upwork customer service is ready to help. They can reach out to the client on your behalf, and even assign a mediation agent if no agreement can be reached.

3. You can make a ton of money on the platform

And of course, the greatest pro is that you can make a lot of money on the Upwork platform. 

I personally pull in about $100,000 per year on the platform and I am on track to cross the $600,000 mark this year.

And I’m not alone.

Freelancer Josh Burns, a SQL Server DBA, has earned over $700,000 on the platform.  

I will openly admit, it can be hard to land those first couple of gigs on Upwork. It took me almost two weeks to get my first little nibble after consistently applying nearly every day.

But after a while, you start to get a feel for exactly what to say and how to pitch yourself to prospective clients. At least I did.

Read Also: How I got my first job on Upwork: Advice from a $500k freelancer

Today, I keep my Upwork profile set to “not available” because I stay so busy I don’t have time for new work.

Speaking of which, I’ve also used Upwork to hire subcontractors as well. Delegation and hiring out for some of the more monotonous tasks have significantly improved my bottom line, helping me make even more money along the way.

It all sounds great so far, right? 

Well, buckle up because now we get to the “cons” portion of the article. 


Upwork Cons:

1. You have to pay to play

In prior years, freelancers could bid on as many jobs as they wanted for free.

But this caused issues for the platform. 

Namely, jobs were being flooded with too many, often underqualified, candidates. 

Believe it or not, many Upwork freelancers indiscriminately apply for jobs without even reading the job post or taking the time to consider whether or not the job is even right for them. 

And so, in May 2019, Upwork introduced something called “Connects”. 

Upwork Connects essentially act as a digital internal currency or credit.

Today, freelancers have to spend 1-6 Connects for each proposal they send (depending on the size of the job). 

This encourages freelancers to be a bit more discerning when applying for jobs.

At the time of this writing, Upwork Connects cost $0.15 each and are sold in bundles of 10, 20, 40, 60 and 80 (for those interested in a bulk discount).

While Upwork gives all new users 40 free Connects to start, most new Upworkers tend to blow through that first allotment pretty quickly and will end up purchasing more.

Now, there is some good news here – you don’t have to spend any Connects to apply for jobs to which you were invited. And most senior freelancers on the platform end up (mostly) only replying to invites over time and ignore the job feed altogether. 

And the longer you’re on the platform, the more invites you’ll start to receive. I personally haven’t used or purchased any Connects in years.

Plus, you receive free Connects every time you win an interview. The more interviews you win, the more Connects you begin to rack up.

In summary, the bulk of this expense will occur during your early days on the platform … when you aren’t winning interviews as often and aren’t receiving invitations to apply.

It’s one of those things that gets easier with time.

2. Upwork charges a commission

And this is everyone’s number one complaint about the platform – Upwork’s commission fee.

At the end of the day, Upwork is still a business. They have business expenses, employees to pay and investors to make happy.

They have to make money.

And the bulk of that money is made through their commission fee. 

The fee breaks down, per client spend, like this:

  • Less than $500: 20% fee
  • $500-$10,000: 10% fee*
  • Over $10,000: 5% fee
  • Clients you bring to the platform: 0% fee

*Enterprise clients remain at 10% even after you hit the $10,000 mark.

While 20% may seem steep, do keep in mind that’s only on the first $500 per client (essentially $100 per client). After that, the fee immediately begins to drop. 

Read Also: How to avoid Upwork fees: Ways to reduce fees from a $500k freelancer

This is why I always recommend Upworkers try to focus on longer-term contracts – fewer fees and more predictable, steady income.

In fact, most of my contracts are now at the 5% mark.

And again, the thing that keeps me using Upwork is that I personally feel like 5% is a good deal given the other services they offer in exchange for that fee (see “pro” number two above).

Lastly, I offer this food for thought … one has to keep in mind that Upwork is not entirely different from a recruiting agency. And the average recruiting agency fee is closer to 30% and doesn’t reduce that percentage over time. 

I tend to argue the 20% isn’t really that high, at least when compared to industry-standard commissions.

3. You have to keep the client on the platform for two years

Want to get out of paying that Upwork fee altogether? No problem, after two years you’re allowed to take your client off the platform and work with them directly. 

However, taking your client off-platform early without paying the conversion fee (an estimated 12% of the freelancer’s estimated annual earnings on Upwork) can result in a permanent suspension of your account. 

While this may seem unfair, I always advise not to bite the hand that feeds. Two years will come and go before you know it.

There you have it, the three biggest pros and cons about the Upwork platform – at least in my opinion. 

For me, the cons have never outweighed the pros.

Upwork gave me the lift I needed to break free from a job I rage-quit back in 2017.

Sure, it was hard to get started. Sure, I’ve paid a lot of fees to the platform. But it’s also been an amazing tool in my freelance arsenal that I wouldn’t exchange for the world.

But I am curious, what do you think? Do the pros outweigh the cons? Let me know in the comments below. And don’t forget to connect with me on social media – I’d love to hear from you!

2 thoughts on “Pros and Cons of Upwork 2022: An analysis from a $500k freelancer”

  1. What always slightly annoys me about Upwork is that while yes, it’s nice that they handle contracts, billing, etc — use of the platform comes with a whole extra set of Upwork-specific mental overhead that you need to think about (what will this action do to my JSS? how should I budget my connects?). And the skills and knowledge you acquire over time to deal with these things are obviously very platform-specific, and often not intuitive to new users. So users end up locking themselves into the Upwork platform, when they’d be better served by using multiple channels.

    (Obviously that’s fine if you’re happy working on Upwork exclusively, but I always advise people to diversify! Avoid single points of failure, etc.)

    Perhaps one for your cons column? 🙂

  2. Oh! I love this one! It’s so very true. Even at my level, I tend to stress out about hounding my clients for positive feedback at the end of an engagement. The pressure to maintain a perfect record on Upwork is unreal!

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