Issa Rae Explains
Issa Rae has built her reputation on sharp instincts and a knack for turning awkward truths into comedy gold. But away from the cameras, one of her boldest leaps nearly dismantled everything she had worked for. Long before Insecure turned her into a household name, a series of hasty choices left her teetering on the edge of financial collapse.
That story, both sobering and self-deprecating, is one of many Rae unpacks in her new essay collection, I Should Be Smarter By Now. In one of the standout pieces, fittingly titled I Almost Know What I’m Doing, she revisits a period in 2014 when ambition and impulsivity collided in ways that nearly emptied her bank account.
At the time, Rae was riding the momentum of her viral success with Awkward Black Girl and trying to translate internet fame into mainstream opportunity. Hungry to create space for marginalized voices in television, she poured her energy into ColorCreative, the company she co-founded with longtime collaborator Deniese Davis. The mission was noble, but the execution would prove to be financially reckless.
She recalls the moment her business manager delivered the kind of call no artist ever wants to receive: “Every penny you’ve saved is about to disappear.” The warning hit like a punch to the chest. Years of hustling, saving, and building her brand were suddenly at risk of vanishing.
The trouble had begun months earlier when Rae started meeting with writers and soliciting new ideas without securing the funds to actually produce them. She envisioned three pilots that could showcase overlooked talent and help push the industry forward. What she didn’t envision was just how expensive those dreams would be.
With no studio backing, she and Davis went knocking on doors, pitching to investors, hoping someone would believe in their vision. The rejections piled up, leaving them with little more than passion and a growing list of financial obligations. Still, Rae pressed forward, convinced that persistence alone could make up for capital.
Her second gamble was even riskier. She decided to call on an old flame — a wealthy ex-boyfriend who, she knew, harbored aspirations of producing projects in Africa. Rae framed her pilots as the stepping stone to his bigger goals, the gateway to building the legacy he claimed to want. To her relief, he agreed to fund the venture.
That commitment gave her a false sense of security. Believing the money was locked in, she kept momentum going: scheduling shoots, meeting with creatives, putting down deposits. The train was speeding ahead, and she didn’t hit the brakes.
Then came the third and most devastating misstep. Just one week before cameras were set to roll, she and her ex got into a heated argument. The fallout was messy, personal, and, most importantly, financial. The check she was counting on never arrived. Suddenly, she was left holding the bag for every single expense.
By then, every major studio they had approached had already declined to partner on the projects. With nowhere else to turn, Rae faced an excruciating choice: shut everything down and cut her losses, or take on the burden herself.
She admits she should have walked away. She didn’t. At that point, her account held roughly $75,000 — money that represented her entire career savings, plus part of the advance for her first book. The costs to finish the pilots, however, would balloon to double that. “What I didn’t have,” she remembers, “was $150,000.”
The realization that she was effectively gambling her entire livelihood was what prompted her manager’s frantic phone call. Years of discipline, every paycheck earned, every speaking gig, every royalty — all of it was about to go into a project with no guarantee of return.
In hindsight, she laughs at the audacity of it all. “I should have stopped,” she admits in the essay. “But I kept going.” To her, abandoning the dream would have felt like admitting defeat, like conceding that her belief in underrepresented stories wasn’t worth the risk.
Against all logic, she completed the shoots. The pilots were filmed, packaged, and polished, ready for the world to see. Yet, in the end, not one of them was picked up. The industry wasn’t ready to invest in what she was offering.
Still, the experience didn’t sink her. If anything, it became a formative lesson in the double-edged nature of her personality. Rae has always been candid about her tendency to leap before she looks. That recklessness has brought her both her biggest breaks and her scariest setbacks.
“My impulsivity is a gift and a curse,” she reflects. “It makes me fearless enough to chase what I want, but it also blinds me to the consequences.” The balance between those extremes continues to shape her career.
Looking back now, the story reads almost like a cautionary tale wrapped inside a comedy of errors — the kind of thing only Rae could narrate with humor and humility. But at the time, it was no laughing matter. It was survival.
The irony, of course, is that her near-collapse came just before her career skyrocketed. Within a few years, Insecure would premiere on HBO, launching her into a new stratosphere of influence and stability. That contrast makes her 2014 gamble all the more striking: she almost lost it all right before she gained everything.
Today, Rae is not only a star but a mogul — a writer, actress, producer, and entrepreneur who continues to open doors for others. Yet she carries with her the memory of nearly losing every cent she had. It’s the kind of scar that humbles even the boldest creator.
And while she can laugh about it now, she hopes readers take something more away from her essay than just amusement. The story isn’t about failure, but about the messy, often expensive process of chasing a dream. It’s about risk, resilience, and the lessons you only learn when you’ve been dangerously close to falling apart.
