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Issa Rae Gets Candid on Mistakes, Money, and Staying True in New Essay Collection

The 'Barbie' star reflects on near financial ruin, her childhood dreams, and the power of staying unapologetically authentic.

Issa Rae is spilling gems in her new book, revealing the one trait she had to shed in order to keep from going broke.

The “Insecure” star just released her latest book, “I Should Be Smarter Now” a six-essay collection that unpacks the setbacks, high-stakes risks, and hard-won successes that shaped Rae into the powerhouse we know and love today.

In one of the essays, Rae admits her impulsiveness in the past almost cost her financially while trying to fund three television pilots with her ColorCreative partner Deniese Davis, VIBE reported

“My impulsivity, the character trait I’ve benefited from and paid dearly for, is both a gift and a curse,” she wrote in the essay. 

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She then lets readers know about a promise her wealthy ex made to fund her projects and help her with her vision, only for a fallout between the two to occur, leaving “The Photograph” star to deal with the costs. 

“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,” she said. 

She pulled from her savings and from her first advance for her first book, “The Misadventures of an Awkward Black Girl,” producing all three pilots, with none of them getting picked up. 

The book also features the “Barbie” star reflecting on her childhood and her discovery of what she calls her “superpower of collaboration,” while staying unapologetically herself. Fans can read these stories in the essays “The Business of Being Me” and “Playing Well with Others,” respectively.

In June, while exclusively announcing the book to People, the entrepreneur shared that the essays are “part confession, part reflection, and part ‘here’s what I wish I’d known.’”

“From dreaming of briefcases as a child to running her own media empire, Issa's creative evolution is both hilarious and inspiring,” publisher Julia Sommerfeld said. 

“These essays capture her remarkable journey with the wit, wisdom and real talk that has made millions of people feel seen."

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