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.
On Tuesday, Aug. 26, the 40-year-old writer and producer released “I Should Be Smarter By Now,” a collection of six essays chronicling her career highs and lows, including how a risky move nearly left her flat broke.
“My impulsivity, the character trait I’ve benefited from and paid dearly for, is both a gift and a curse,” the “Insecure” alum wrote, per US Weekly. “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.”
The best example of how her impulsivity, combined with her being a self-described “underthinker,” has led to learning experiences she could recall almost cost her “every single dollar” she had ever made in her life.
The “Little” star recalled how, in 2014, when she and ColorCreative partner Deniese Davis first launched the company, they did so by attempting to produce three TV pilots without secured funding. Rae reached out to a “rich ex” who initially promised to invest a third of what they needed. However, the two ended up fighting, leading the ex to ultimately leave them high and dry.
“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,” wrote the “Barbie” actress.
She needed $150,000 and had roughly half of that at the time, thanks to her advance for her first book, “Adventures of an Awkward Black Girl.”
She added, “Most of it was in my savings — it was all the money I had ever made in my life up until that point.”
In the end, Rae and Davis managed to shoot all three pilots with Rae as the main financial backer; however, they didn’t find homes for them.
Although the gamble may not have yielded immediate success, it laid the groundwork for ColorCreative to grow and for Rae to refine her business instincts.
Alongside that story, the Emmy nominee delves into topics such as creativity, collaboration, and resilience in essays titled “The Business of Being Me,” “Playing Well with Others,” “The Geography of Creativity,” “I See You Seeing Me,” “The Art of Strategic Procrastination,” and “I Almost Know What I’m Doing.” Rae describes the collection, released in partnership with Amazon Prime and Audible, as a way of sharing the messy, unpolished truth behind her success.
“This collection is part confession, part reflection and part ‘here’s what I wish I’d known,’” Rae told People magazine in June ahead of the release. “But mostly it’s just me being honest about the weird, wonderful journey from having big dreams to making them a reality.”
In a post announcing the release on Instagram, Rae wrote, “My new book, “I Should Be Smarter By Now” is officially out today! If you’re dreaming about OR in the midst of building something — I wrote these stories for you.”
She also announced that she will embark on a six-city book tour, starting Sept. 8 in Philadelphia and stopping in Atlanta, Washington, D.C., Dallas, Chicago, and Detroit.
