The Struggle is Real

By Kindsey Young

Everyone started somewhere. Check out some of the odd jobs the crew of Insecure had before working on television sets.


What’s Issa’s actual passion? Becoming more and more fed up with her financial situation this season, Issa starts to really think about her career. She’s been juggling multiple jobs — working at We Got Y’all and driving Lyft — and she just inquired about a property manager position. It doesn’t all seem to track. A lot of people have had a journey similar to Issa’s, and this episode made me think of all the things people do to get to where they want to be. With this in mind, I spoke with some of the Insecure crew and asked them to share some jobs they had before getting their “dream job.”

Here are some of the ones I heard:

My first job was as a cashier at Target. I was 17. Then I worked at TGI Fridays — it was my summer job for a couple of years. After college, I somehow ended up working at a salad place for three weeks because I thought if I didn’t have a job (any job) right away, then I was a failure. I guess 21-year-old me thought salad equated to success. And after that, I got my first “real” job at Gallaudet University, which is a prestigious university for the deaf in D.C. (Yes, I know sign language. #FunFact.) I worked in video production there for five whole years before landing my first industry opportunity in Los Angeles.

The truth is, sometimes, the struggle is real. Not many people get their dream job right out of the gate, or even know what their dream job is. But like Issa, while you’re trying to figure out what that passion is, you still have to make ends meet. They key is to keep your eye on the prize. Chances are, anything you’re doing is helping prepare for the future — maybe in ways you won’t even realize until later. Does We Got Y’all really have Issa? Is driving Lyft taking her down the right road? Could managing property play a role in Issa learning to manage her priorities? Probably not. But still, it sounded clever and my point remains. Alexa, play “Everyday I’m Hustlin’’’ by Rick Ross.

Check out new episodes of Insecure every Sunday at 10:30 pm, and head to the Blogger-Like page for updates all season long.