Issa Rae Explains How She Almost Went Flat Broke Early On In Her Career

Issa Rae may be known for “Insecure,” but it was her impulsivity that almost landed her in a horrible financial state that could’ve cost her every single penny she’d ever made. And now, she’s opening up about it.

The revelation is just one of many that’s shared in her newly published collection of short stories entitled “I Should Be Smarter By Now.” In the essay entitled “I Almost Know What I’m Doing,” Rae recalled the time in 2014 where she made a series of unfortunate decisions that led to her almost losing everything she’d worked for up until that point.

She explained how in 2014, she got an alarming call from her business manager who told her that “every penny you’ve saved is about to be gone.” The reason why she was about to see her savings tank was because she decided to work on bringing three different TV pilots to life through her company ColorCreative, her independent TV company dedicated to breaking underrepresented writers that she co-founded with her producing partner Deniese Davis.

Per US Weekly, Rae’s first bad decision came when she started soliciting scripts and meeting with potential writers before she even had the funding secured to help undergird their visions. Though she and Davis went around looking for potential investors, they didn’t get the results that they were looking for.

Rae’s second bad decision came when she decided to reach back out to her “rich ex” to see if he would cut a check for the dream project she was trying to build. Despite their rocky history, they still kept in touch. Knowing that he had aspirations to eventually invest in TV and film projects in Africa, Rae positioned the idea as “the gateway [for him] to be able to ultimately produce there.”

So with a check seemingly secured, she continued on meeting with writers and setting things up.

However, her third bad move happened when she and that same ex got into a major fight just one week before filming for the pilots was set to begin. And the timing couldn’t have been worse because at that point, every studio they reached out to had essentially passed on what they were offering.

Due to everything that transpired, Rae said that she should’ve pulled the plug when she knew she didn’t have the funding as all of the costs would fall back on her. And while she had about $75,000 in her account, going forward with the pilots would drain her of everything and put her over.

“Let me tell you what I didn’t have in my bank account: $150,000,” Rae explained. “I had about half of that because I had received part of the advance for my first book. Most of it was in my savings — it was all the money I had ever made in my life up until that point. Hence, the frantic call from my business manager.”

Thankfully, the story has somewhat of a happy ending. Rae was able to film all the pilots, even though none of the shows got picked up. But the moment was enough for her to reflect on how her impulsive decisions don’t always lead to the best outcomes.

“My impulsivity, the character trait I’ve benefited from and paid dearly for, is both a gift and a curse,” Rae said. “The gift is that I can be fearless in the pursuit of anything I want to achieve. If I want something, I’m going to be active and go after it. The curse is, of course, that I don’t properly think through the consequences of my actions.”