Why You Shouldn’t Hesitate to Claim Unemployment Benefits After Losing Your Job

At my latest networking “meeting” with my bro Alex — also known as a free lunch with a marketing executive who still has a job and a corporate card — we talked about freelance opportunities that might be coming up. We discussed who was hiring, who claimed they were hiring, and which companies were pretending that “lean teams” were somehow a point of pride instead of a warning sign.

As we were wrapping up, Alex asked about my runway. “How much longer do you have on unemployment?” he asked, while signing the check. “I never filed for unemployment,” I said. Alex looked at me the way people look at you when you say you’re Team Aubrey. “What do you mean you never filed?”

I tried to explain it, but halfway through talking, I realized how ridiculous I sounded. I had somehow turned unemployment into this mythical government charity dungeon in my mind. In my head, getting unemployment meant going to someplace with flickering fluorescent lights where desperate people sat in molded plastic chairs waiting for a number to be called. It felt like something other people did. Not me.

When I first wrote publicly about losing my job, I joked about “funemployment.” At the time, I still had severance money coming in, savings, and enough confidence to believe another role would appear quickly. And as we now know… you could end up dealing with the five stages of grief every time you see an e-mail that starts with: “Thank you for taking the time…”

I am drained and have been for quite some time. The idea of applying for… money with no attachment except that I’m entitled to it just didn’t connect. The truth is, I didn’t understand unemployment at all.

Common Misconceptions About Unemployment Benefits

• Does severance disqualify you? No, it does not.
• Are high earners eligible? Yes, they can be.
• Do freelancers qualify? Yes, but they are often treated differently.

Most embarrassingly, I didn’t understand that unemployment insurance isn’t charity. I knew, in theory but not in practice. Since my very first job as a teenager, employers have been paying into unemployment insurance systems tied to my labor. Decade after decade. Every paycheck. Every W-2. Every promotion. Every “exciting opportunity.” Every year-end review where someone called me “valuable to the organization” right before letting me go.

“You’ve probably generated like $30K into unemployment systems over your career,” Alex said. “Why are you acting like you’re asking somebody for a favor?”

That was the part that snapped something into place for me. Because I realized my resistance wasn’t financial. It was psychological. I had attached filing for unemployment to failure. I thought filing meant I had somehow crossed into another category of person. The kind of person waiting for help instead of being the one taking the lunch meetings and giving career advice.

But unemployment isn’t a character judgment. It’s literally insurance. Your labor helps fund a system that exists for