Here’s Why Freelance Platforms Like Upwork Are Broken

Delton Rhodes
The Green Light
Published in
7 min readJul 31, 2019



After graduating from college in 2015, I began building my portfolio in content writing and content marketing. I was fortunate enough to find a few short-term freelance opportunities on freelance sites like Upwork. Slowly, I was able to learn how to write viral content and build an amazing portfolio. I was eventually able to find higher-quality jobs on some of the top online job boards (see my favorites list here). Along the way, I experienced several issues with freelance sites like Upwork, Fivver, and Freelancer. While the quality of user experience (both for freelancers and clients) on these freelance platforms has always had issues, this seems to be more apparent than ever in 2019. Here are the major problems freelancers and clients face today.

Upwork Now Charges Freelancers to Apply

Beginning in May-June 2019, we started to see major changes in the way that Upwork operates. Freelancers first learned about this in April 2019.

Part of an email I received from Upwork on April 2, 2019

Looking at my own profile in early July 2019, I thought that I had 0 available connects when the site implemented these changes. This means that I would have had to buy connects immediately in order to apply for one project. However, looking at my profile on July 30, 2019, I discovered that I actually had 60 connects available. I hadn’t paid for connects, so I guess my previously unused connects rolled over or Upwork granted them to me for whatever reason.

From the perspective of someone posting a job on freelance websites, I understand the need to find candidates who are serious about completing projects. However, many of the projects posted don’t pay nearly enough for freelancers to justify investing not only time to write a tailored cover letter but now funds as well. I know there are many job boards out there (i.e. FlexJobs or The Ladders) that require job seekers to pay money in order to access job listings. Even though I disagree with this model, I at least know that the listings posted on these job boards are higher-quality on average than freelance platforms.