Issa Rae’s “impulsiveness” has landed her in some sticky situations over the years — and, sometimes, it has cost her.
“My impulsivity, the character trait I’ve benefited from and paid dearly for, is both a gift and a curse,” Rae, 40, wrote in her new essay collection, I Should be Smarter by Now, released on Tuesday, August 26. “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.”
She added, “Some creatives can’t get their projects off the ground because they overthink. I’m an underthinker. The best example of this cost me every single dollar I had ever made in my life.”
Rae teamed up with Amazon Original Stories to release six essays on Tuesday, including the essay titled, I Almost Know What I’m Doing.
Rae explained that in 2014, she was already a full-time writer and had “a few web series” under her belt. The Insecure creator was also in the process of “writing a book,” which included a substantial advance payment. (Her memoir The Misadventures of Awkward Black Girl was published in 2015.)
“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.”
The actress’ business manager informed her that “every penny you’ve saved is about to be gone.” Rae then broke down the three major mistakes that landed her nearly broke, which started with her decision to work on three TV pilots simultaneously alongside her producing partner, Deniese Davis.
“We could discover three diverse comedy writers via a call for script submissions through our vetted network,” she explained. “After several planning calls and texts back and forth over the course of a week, Deniese and I started ColorCreative, an independent TV company dedicated to breaking underrepresented writers. Now we just needed the money to fund the pilots.”
Rae’s first mistake came when they “set a schedule and started soliciting scripts and meeting writers without securing the money first.” While both she and Davis were on the hunt for investors, neither were “getting many bites,” Rae wrote.
“I was so excited about our undeniable idea and confident that we eventually would, so we proceeded anyway,” she explained. “We found some really great scripts that, to me, were filling a void in television.”
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Mistake No. 2 came when Rae decided to reach out to her “rich ex” for funding.
“Despite our turbulent history, we stayed in touch, and he was always interested in investing in film and TV,” she explained. “More specifically in Africa, but I told him this model was the gateway to be able to ultimately produce there.”
Rae and Davis kept “pushing this forward” because said ex would front “at least one-third of the money.” Then, Rae “got into a fight with said ex a week before we were scheduled to shoot,” which ended up being her third mistake.
Their argument came “after we had gotten polite passes from most of the studios we had met with,” she recalled.
“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.”
Despite the money issue, all three pilots were shot with Rae as the monetary backer. While the creators never found homes for any of the projects, the situation did allow for future projects with Rae and ColorCreative.