My first full month on Upwork; the triumphs, the confusion, and the outrage!

Is Upwork a good way to start out as a beginner? Is it the enemy of freelancers? Is it evil incarnate? Here’s what I found out

Claire McGregor
6 min readNov 1, 2020


Photo by Per Lööv on Unsplash

If you’re in the freelancing business then you’ll probably have heard of Upwork. There have been lots of articles here on Medium about it and everyone has an opinion. Some think platforms like Upwork are the devil. Others think it’s ok as a way of earning some extra cash if you go into it with your eyes open. This begs the question if there are lots of people writing about it already what’s the point of this article?

It a fair question. I did think it over a lot while deciding if I had anything to add to the discussion. After a bit of navel-gazing, I decided that I did. Many of the existing articles were written by established freelancers. They had/have other options to find work. That’s not where I am. If you’ve been kind enough to read any of my previous pieces, you’ll have noticed I am a beginner. They are amateur pieces of writing which I’m sure I’ll cringe at when I re-read them in a year. Everyone has to start somewhere though.

The purpose they served was getting my feet wet and also deciding if writing is something I enjoy. To my delight, I have discovered it is. Whether I’m writing for my blog, publishing here on Medium, or writing for a client I get so much satisfaction from it.

I am still working full time. I hope with time, perseverance, and a little luck I can make writing my career. I’ve come to see my job as something I want to get through as quickly as possible so I can move on to my real work.

Enter Upwork

That brings us to Upwork. I wanted to make money with my writing. To see if I write well enough to both get paid and have happy clients. I read many of the wonderful articles here about how to start out in freelancing. Many of them despise Upwork and list all the other ways to get clients. Almost all involved networking. I am not good at networking.

I am fine having a chat with people as I’m pretty friendly but when it comes to any kind of selling I freeze. I left a reasonably well-paid job that I’d been in for…



Claire McGregor

I’m a writer taking my time to learn what good writing’s about and get my blog off the ground. I want to connect and learn. My Blog