Freelance | Career

The Pros and Cons of Upwork Freelancing

You’ll find good work but watch for red flags

Shannon Cheesman
The Startup
Published in
7 min readMar 17, 2021

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Photo by Adeolu Eletu on Unsplash

A while back, 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 at that time coronavirus was in full swing, so 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. Here are the pros and cons I discovered:

What’s Great About Upwork 😃

There‘s 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.

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Shannon Cheesman
The Startup

I’m a marketing copywriter with a background in TV news. I’ve written everything from blogs to breaking news stories (and everything in between) in my career.