Issa Rae Reveals How She Almost Lost ‘Every Single Dollar’ She Ever Made

Issa Rae Reveals Character Trait Of Hers That Could Have Left Her Broke

In Issa Rae's new six-essay book 'I Should Be Smarter by Now,' she got candid about a moment in life where she could have lost it all with one thing.

Issa Rae Explains How She Almost Went Flat Broke Early On In Her Career

In her new, book Issa Rae reveals the series of unfortunate decisions that led to her almost losing everything she'd worked for up until that point.Read more...

Issa Rae Reveals How She Almost Lost ‘Every Single Dollar’ She Ever Made

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 a…

Issa Rae Says ‘Impulsivity’ Almost Cost Her All Her Savings After Proceeding With A Project That Lacked Full Investor Buy-In

Her personality trait attributed to her by Issa Rae, which may have caused her own grief

Issa Rae, an Emmy-nominated producer and actress, has turned her life's work into a career-changing book, I Should Be Smarter By Now, which...

BLK ALERTS - Issa Rae recalls an early mistake that nearly cost her every cent she’d made

Issa Rae attends the 2025 Met Gala Celebrating “Superfine: Tailoring Black Style” at Metropolitan Museum of Art on May 05, 2025 in New York City. (Photo by Savion Washington/Getty Images) Writer and producer Issa Rae releases new essay collection “I Should Be Smarter By Now” in partnership with Amazon and Audible. Issa Rae is back with a new book that gives a candid look at some of the lessons she’s learned thus far in her career in Hollywood. O…