The Pros and Cons of Upwork Freelancing

Woman sitting at table and typing on laptop.
Photo by Amelia Bartlett on Unsplash

Last year, I decided to try my hand at a little freelance work. The idea was to make a few extra bucks on the side doing what I love to do — writing. And with coronavirus in full swing, I had lots of extra time at home after work to focus on a side hustle.

Upwork is one of the most well-known freelance platforms out there, so I chose to join. It has been a little over six months since my little experiment, and here are the pros and cons I have discovered.

The Pros of Upwork Freelancing

There Is Lots of Work Available

If you have marketable skills and can deliver a quality product to clients, you can find jobs on Upwork and get hired.

I admit that, at first, I was dubious about my ability to land an opportunity. But I was pleasantly surprised when a client first responded to me.

My particular skill set is in copywriting, and it took me about a month of submitting proposals (a LOT of them) to land my first gig. I completed my first job expertly, delivered the final product earlier than the client expected, and was rewarded with prompt payment and a glowing review.

That was the springboard I needed to land several more gigs, and I also now have two return clients who have since hired me for additional work.

It took about six months to land eight paying gigs and get enough positive reviews on my profile to make me look like a rockstar writer. I have also earned a 100% Job Success badge, which lends me extra credibility.

And now, I am starting to get the added benefit of receiving invitations to apply for job listings. Clients find me when searching for freelancers, review my profile, and, if interested, reach out to see if I would like to collaborate with them.

Upwork Makes Getting Paid Easy and Reliable

On Upwork, a client will either set up their project with a fixed price or set an hourly rate.Most of my projects have been at a fixed price where I have been paid an agreed-upon cost at completion.

You can also choose to break up a project into milestones and get paid in increments as you go along. My projects have been small so far, so I have not selected to go that route. But milestones make perfect sense for large projects.

I completed one project at an hourly rate. Upwork will automatically track your time via a desktop app that you download to your computer. You open the app, log in to the contract, and begin working.

On the client’s side, they see the time you have spent on their project, can view your work diary and screenshots of your work progress.

Payment Protection

Upwork’s Payment Protection gives me peace of mind.

When I enter a contract for a fixed-price project, for example, the client deposits money into an escrow account where the funds are held until the project is complete. This allows me to work without wondering if the money will be there when I finish a project.

For hourly contracts, clients are invoiced based on the hours I log in to Upwork. It is kind of like getting a paycheck from an employer. Upwork has payment protection for hourly contracts in place that will protect me if I run into an issue getting paid.

Upwork Clients Tend To Move Fast

Upwork clients have a job to do, and they don’t mess around. I have found that once I begin a conversation with a client if they are interested, they hire me immediately. The next thing I know, I have a contract, and away I go.

I love it because I am not wasting time going back and forth with someone who may or may not end up being a client. A decision is made, I receive a contract, and I am working.

The Cons of Upwork Freelancing


Some clients are great at communicating with you. Some are not, and you will need to keep prodding them.

It can be frustrating. However, I remind myself that clients can be very busy. I practice patience and make sure that I keep up my end of the bargain by communicating regularly.

Low Paying Jobs That Aren’t Worth Your Time

Every freelance writing platform has low-ball listings such as $5 for a 2,000-word blog article.

I beg you — please do NOT stoop to that level, no matter how badly you want to freelance or how long it may take to find something that pays decent money. Do not sell yourself short.

The Scammers

Scammers are EVERYWHERE online, and it is challenging to escape their presence. Your best defense is to use your common sense and look for red flags.

I have been approached by a few scammers on Upwork and so far have been able to steer clear of getting involved with them. I know what doesn’t seem right, and I am diligent in reporting to Upwork anything fishy I might run across.

In case you are wondering, here are some of the more common Upwork scams:

Ask freelancers to provide a free ‘sample’ for evaluation.

There is no evaluation. The scammer is trying to get you to do free work for them. Once you hand your work over to them, you will never hear from them again.

I have had a few of these requests come my way, and as soon as I say I need to get paid for the sample, I am ghosted.

However, one reputable client paid me my full rate to write a sample blog post, and I was happy to oblige.

Try to get you to conduct business outside of the Upwork platform.

Going outside of the platform is a big no-no on Upwork — it is actually against their Terms of Service.

Recently, I was invited to interview for a job that was right up my alley and sounded legitimate. But as soon as I responded to the invite, I was asked to download a Telegram instant messaging app, and the interview would continue there. Of course, I immediately knew this was a scam. I declined the job right away and then reported the situation to Upwork.

Ask you to share your account information.

The ploy they are trying to sell you on is that the two of you can work together, and your earnings will increase.

This attempt, of course, has the word scam written all over it. The scammer wants access to your Upwork account so they can get at the financial information you have stored there. And believe me, they will lock you out once they get in.

For in-depth tips on avoiding scams on Upwork, read this article by fellow Medium writer Cat Webling: Don’t Scam and Don’t Get Scammed on Upwork

Upwork Fees

Some people hate Upwork’s 20% fee, and I agree it can seem high. But I consider their cut the cost of doing business.

Upwork saves me from having to deal with the hassle of handling my contracts and payments. I don’t have to worry about billing clients or trying to collect money owed to me. All of that is taken care of seamlessly on the Upwork platform.

It is also important to note that there are discounted fees for working with a client long term, or on a large project:

  • Once you reach a lifetime $500 threshold with a client, the fee is 10%.
  • If you are fortunate enough to reach a lifetime threshold of over $10,000 with a single client, the fee is 5%.

Now I do pay a subscription as well — $14.99 monthly for the Freelancer Plus plan. The additional expense is optional, but I choose to pay it every month because of the perks I get:

  • Competitor bid ranges — high bids, average bids, low bids. This is very helpful for determining how much I should bid on a project.
  • A bulk amount of ‘Connects,’ which are like tokens you use to submit proposals to jobs. I receive 80 Connects each month, and it takes 2–6 of them to submit a proposal, depending on the listing.
  • My earnings are kept confidential, which can be helpful if I decide to raise my hourly rate.
  • I can take a break from Upwork, and my profile will remain active, and prospects will still be able to find and contact me.
  • custom URL, which I use to promote my freelance business name, Blue Blossom Writing.

Of note: I do a separate little side hustle, UX Testing, to cover the $14.99 monthly subscription cost, and that has been working out quite well.


I am happy with Upwork because it makes it easy to do a few gigs here and there to supplement my regular income. As a side hustle, it is a great platform — I enjoy working with a variety of clients, and I love how easy it is to get paid. (Of note, because I do have a day job, I do not accept any assignments that might be a conflict of interest.)

I am not relying on my Upwork income to pay bills or keep a roof over my head, so I cannot comment on using the platform as a sole income source. I am sure it can be done, and I have read plenty of articles about Upwork superstars who do just that. For me, at this point in my life, it is simply a way to earn a little extra money for doing something I love to do.

As with any platform, there are scams to watch out for. As long as you keep your wits about you while navigating Upwork, you will be fine. Their platform is designed to protect you as well, so if you do end up running into a problem, there is a way to resolve it.

Landing your first job on Upwork might take a little while. Do not get discouraged. Just keep submitting those proposals. And don’t be tempted by the extremely low-paying listings. It is a waste of your time — there are clients on Upwork who will pay a market rate.

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