Issa Rae is providing examples of how her impulsive streak led to significant financial risks early in her ascent up the Hollywood ranks.
In her new essay collection, I Should Be Smarter by Now, released Aug. 26, Rae reflects on how her impulsive nature shaped both her successes and financial struggles early in her career. Among the six essays available on Amazon Original Stories, I Almost Know What I’m Doing details how her impulsiveness nearly left her bankrupt.
“My impulsivity, the character trait I’ve benefited from and paid dearly for, is both a gift and a curse,” Rae wrote, as captured by Us Weekly. “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.”
“Some creatives can’t get their projects off the ground because they overthink,” she added. “I’m an underthinker. The best example of this cost me every single dollar I had ever made in my life.”
In 2014, Rae was working full-time as a writer and had “a few web series” under her belt, she recalled. The Insecure creator was also in the process of writing a book, likely her 2015 memoir “The Misadventures of Awkward Black Girl,” which came with a substantial advance. It was at this time that a call from her business manager would shake her world thoroughly.
“I decided to be responsible and pay off all my debt,” Rae explained. “I was on the set of an independently produced comedy pilot called Words with Girls from a new writer I loved and believed in, when I got the call from my business manager.”
According to her manager, “every penny you’ve saved is about to be gone,” and Rae cites three major mistakes she made that almost led to her going broke.
Rae, along with her producing partner Deniese Davis, launched the independent production company ColorCreative. However, before securing any investor funding, they had already set a schedule, solicited scripts, and met with writers. While searching for investors, neither Rae nor Davis was “getting many bites,” she wrote.
“I was so excited about our undeniable idea and confident that we eventually would, so we proceeded anyway,” Rae explained. “We found some really great scripts that, to me, were filling a void in television.”
Mistake No. 2 came when Rae reached out to a “rich ex” for funding, and the third occurred when she “got into a fight with said ex a week before we were scheduled to shoot,” she wrote.
“The real mistake was not pulling the plug when I knew I didn’t have the money and that all of the costs would be falling on me. Let me
tell you what I didn’t have in my bank account: $150,000,” Rae added. “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.”RELATED CONTENT: Elevating Your Excellence: Damola Adamolekun: The Nigerian King Of Red Lobster