There is a saying regarding the fine arts that suggests art often imitates life. And if anyone ever took this phrase seriously, it is our favorite self-proclaimed awkward Black girl, Issa Rae.

As the creator of the YouTube series “The Misadventures of an Awkward Black Girl” and the cult-classic “Insecure,” Rae has been given the world a loosely based look into her life. Her characters are relatable and accurately depict the cohort of millennials she represents. What’s more, they bring the very much-needed comedic relief necessary for surviving adulthood.

With an array of awards and honors under her belt, it is safe to say that Issa Rae is that girl!

But before the fame and the large platform, one of the most relatable qualities about Rae was that she worked hard and got it out the mud like many future, current, and aspiring creatives. So much so that when she once lived in Harlem, New York, she went six months without paying rent and was in for the surprise of her life when the building’s newest landlord came collecting the check.

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Looking To Get Rich

Issa Rae appeared on the debut episode of Direct Deposit, a podcast hosted by Morehouse College graduate and author Chad Sanders.

The podcast is centered around the dynamic of Black people finding their way in the world, searching for financial stability, and balancing wealth while continuing to negotiate what it means to be Black in America.

An Interesting Welcome To New York

On this episode, Sanders asked the creator of “Rap Sh!t,” as means of inspiration, to introduce the audience to broke Issa. At that moment, she noted that it wasn’t until she got to Harlem that she finally realized how broke she was initially.

“I was in Harlem, and I had just graduated and gotten a stipend to move to New York. And I thought I was balling. It was a $6,000 stipend, and I was living in a slum. I didn’t know I was,” Rae described on the podcast. “This random, like, Jewish dude who must’ve been like 24 had shown me this apartment, and I was tasked with finding it for another girl I knew at Stanford, a Black girl.”

A Scavenger Hunt Of Sorts

With the task at hand, she went to Harlem to find this apartment listed on Craigslist, and upon arrival, she found out it was undergoing renovations. Excited about the alleged remodel, Rae and her friend went on to live there for about six months. However, those first six months were unintentionally rent-free.

“We never paid rent for six months cause nobody asked us for it cause I guess nobody owned the building. And, so, we were just like, I guess we’re just living here. And then, of course, six months in, they were like, ‘Oh, we’re the new building owners. You gotta pay up now,” Rae explained during the episode.

Turning Ls Into Lessons

Issa Rae admitted that because they were such “goodie two shoes,” they did not abandon the responsibility. They paid the back rent.

Rae chops this up as a learning lesson, having not known much about money at the time. She also revealed she was working three jobs with a mound of credit card debt.

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It's Been Up Ever Since

However, none of this stopped her dreams. With aspirations to write and create short films, she continued to pursue her passions, which definitely paid off.

Today, Rae owns her own production company, has successful television shows, and films, and stars in top movies.