Issa Rae on the “Gift and Curse” of Impulsivity: How Early Setbacks Paved the Way for Stardom
Issa Rae, the visionary force behind hits like Insecure and a prominent figure in Hollywood, is opening up about the formative — and financially harrowing — experiences that shaped her path to stardom. In her recently released essay collection, I Should Be Smarter Now, the 40-year-old “Barbie” star candidly reflects on the double-edged sword of her impulsivity, a trait she credits for both her ambitious pursuits and her most costly mistakes.
The Double-Edged Sword of Ambition
“My impulsivity, the character trait I’ve benefited from and paid dearly for, is both a gift and a curse,” Rae writes in the collection, as reported by Us Weekly. She elaborates, “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.” However, this drive often came with a steep price: “The curse is, of course, that I don’t properly think through the consequences of my actions.” This self-assessment is particularly poignant when she adds, “The best example of this cost me every single dollar I had ever made in my life.”
The $150,000 Gamble: A Lesson in “Underthinking”
The most vivid illustration of this “underthinking,” as Rae calls it, harks back to 2014. At a pivotal point in her career, having gained recognition for earlier web series but still striving for a breakthrough, Rae and her producing partner, Deniese Davis, embarked on an ambitious venture through their company, ColorCreative. Their plan: to simultaneously launch three television pilots. Despite not having secured any financial backing and receiving “polite passes from most of the studios,” Rae’s fervent belief in their scripts, which she felt were “filling a void in television,” propelled them forward. They began soliciting scripts and meeting with writers, operating on sheer optimism that funding would eventually materialize.
As the production deadlines loomed, the critical need for investment became undeniable. Rae turned to a personal connection, a “rich ex” who had previously expressed interest in investing in film and television projects. He reportedly pledged to cover “at least one-third of the money” needed, offering a glimmer of hope. Buoyed by this promise, Rae and Davis pressed on, committing to the costly productions.
However, this fragile financial lifeline snapped just a week before shooting was scheduled to commence. A fight with the former partner led to his sudden withdrawal of financial support, leaving Rae and Davis in a critical bind. The full weight of the production costs, estimated at $150,000, now rested squarely on Rae’s shoulders.
Rae vividly recounts the financial shock, admitting, “Let me tell you what I didn’t have in my bank account: $150,000.” She revealed that she possessed only about half of that amount, roughly $75,000, which comprised her entire life’s savings up to that point, supplemented by an advance from her first book. The gravity of the situation became terrifyingly real when her business manager delivered the stark news: “every penny” she had ever “saved” was “about to be gone” to fund these three pilots. It was a moment of profound vulnerability, where ambition clashed with financial reality, forcing her to deplete her personal reserves entirely.
From Financial Ruin to Insecure: The Road to Resilience
While none of the three pilots ultimately found a network home, the experience, though financially devastating at the time, was not in vain. This intense period of trial by fire fueled Rae and Davis’s resolve to continue building ColorCreative. The lessons learned, the resilience forged, and the network of talent cultivated during this period became instrumental in their subsequent efforts. This foundation eventually led to Rae’s breakout success with Insecure, an HBO series that garnered widespread critical acclaim and solidified her status as a major creative voice in Hollywood.
I Should Be Smarter Now, offering these and other hard-won wisdoms, is now available for purchase, providing a candid look into the triumphs and tribulations behind one of entertainment’s most influential figures.
Issa Rae: Continuing to Inspire and Innovate
