DC Freelancers & Unemployment: One Freelancer’s Familiar Story of Frustration

On September 16, 2020, three DC-based freelancers testified in front of the DC City Council’s Committee on Labor and Workforce Development about how freelancers experienced the economic pains of COVID-19 uniquely, and how the unemployment system used by the Department of Employment Services (DOES) is not set up for how we as self-employed professionals work.

In this three-part series, you’ll hear from each of the freelancers who spoke to make the case for an inclusive unemployment system for ALL workers, including those working for themselves. Next up is me, Rachel Maisler, an unabashed policy wonk and Founder & CEO of, fittingly, Wonk Policy & Communications, Inc.

 For the first five months of the pandemic, I was one of the lucky ones – especially as an independent contractor. When the world shut down because of COVID-19 in March, my client made a commitment to keep our entire team – employees, temps and contractors alike – on board as long as they could. Every single day, I counted my blessings. 

Fast forward to August 31. I receive THE email: 

Subject: Termination of contract 


[CLIENT] thanks you for your service on the 2020 Decennial Program. At this time, due to COVID-19 constraints on in-person work, and the changing requirements of the program, in general, we are not renewing/extending your contract. Your last day is effective August 31st. We want to thank you for your extraordinary services throughout the program and want to express how much we appreciated your dedication and commitment to the program.

We wish you luck in your future endeavors! 

It was inevitable. My time had come and I would need to file for Pandemic Unemployment. Again, I considered myself to be one of the lucky ones. Early on, my freelancer peers had successfully advocated for independent contractors like myself to be included in the eligibility ranks for this special type of unemployment. 

I knew the unemployment claims system had experienced a myriad of issues early on, from technology to volume and everything in between. I figured though, it had been five and a half months since the pandemic began so surely the issues had been ironed out. How wrong I was. 

On August 31, I went to the Department of Employment Services (DOES) website to begin my claim process. Thanks to intel from fellow freelancers, I knew I’d have to file for regular unemployment insurance, and then follow up with the pandemic unemployment application. 

File for regular unemployment, get rejected, file for PUA. The only reason I have any inkling of the process is because of the Freelance DC Facebook Group

‘Ok,’ I thought to myself, ‘I can handle this. It’s been five months since this all began so it should be smooth sailing.’ 

Little did I know, the process for filing for pandemic unemployment was one of the most confusing I’d encounter in my time as a DC resident. 

The day my contract was terminated, I signed onto the unemployment website. I read the FAQs, skimmed the conversations on the Facebook group, gathered the documentation I thought I’d need. 

I logged onto the site and experienced full on confusion. It was like I entered a time machine that took me back to 2009 when I was laid off from a previous position. The website hadn’t changed, but my circumstances had. I was asked for quarterly income – which thankfully I had from my invoices… hours worked… other things that may have made sense if I was a W2 employee who lost their job, but not as a freelancer/sole proprietor LLC whose primary contract dried up as a result of the public health emergency. 

I filled out the online forms online to the best of my ability… 

Employer: Self 

Reason for leaving: Ummmm, well, I still have my LLC, but I don’t have any contracts right now so I am filing for PUA… is that a box I can check? 

The Sunday following my initial claim, which I should add was followed by a PUA confirmation email, I logged in to do my weekly claim. 


Um, what? I thought we freelancers were supposed to be included. Why am I ineligible? 

I called DOES and spoke with whomever picked up the phone (thankfully it wasn’t a long wait time). They confirmed my application had been received but were unable to give me any other information. 

At this point, I’m so confused, I reached out to Councilmember Silverman. She said the process for PUA usually takes three weeks, and if I don’t hear anything by then to circle back. (Thankfully this hearing is scheduled within that 3-week period!) 

I get it, these things take time, especially when the system has been taxed like never before. 

But here’s my bottom line: The process is so confusing that I don’t even know how it’s supposed to work without the help of a councilmember! (Compared to my experience in 2009 which was pretty straight forward). 

As a freelancer filing for pandemic unemployment, I feel like a square peg in a circular hole. I know I qualify because of the work of this committee, but the forms just don’t make any sense. At one point, I even received a separation agreement from… myself? I don’t even know how to respond to that. 

But I digress. Today is September 16. That’s sixteen days since my contract ended, fifteen days since I filed my initial claim. And what do I have to show? Two weeks of being deemed “monetarily ineligible,” one hopeful email reply from Councilmember Silverman, and oh, I paid my federal and DC estimated taxes yesterday. 

So now, I wait. 

Rachel Maisler

Rachel Maisler

Rachel Maisler is Founder & CEO of Wonk Policy & Communications, LLC, a boutique consultancy offering a wide range of services to help organizations navigate the health, education, and transportation policy landscapes. Learn more at www.wonkpolicy.com.