I Should Be Smarter By Now

Even at seven years old, Issa Rae meant business, conducting herself with entrepreneurial authority on a toy phone in her bedroom. Eventually, it was a matter of convincing others that she had a lot to say and getting them to listen. From her first web series, Awkward Black Girl, to network disappointments to HBO triumphs, Issa charts her aspirational journey—self-doubts and all—of being taken seriously, finding her voice, and shaping it into a groundbreaking career.

Issa Rae preferred working alone. She was particular that way. But as her career grew, she understood that sharing control didn’t necessarily mean losing it—or her vision. And that sometimes, carefully chosen Hollywood allies could actually enhance it. From rom-coms to blockbusters, from writers’ rooms to film sets—including Barbie—the former independent spirit discovers the superpower of collaboration while remaining unapologetically herself.

Issa Rae was born in Los Angeles but never felt she was quite the city’s type. Though each inspiration destination—from Potomac to Harlem—left its mark, Issa chases her dreams back to her sun-soaked roots. It’s there that Issa finally finds her voice, her wings, and the vibrant heartbeat of a creative community. Issa’s true muse had been waiting all along for her to come home.

Remember a mortifying moment that made you self-aware? Honestly, Issa Rae remembers a few. In this illuminating essay, Issa follows her shoulda/coulda/woulda journey from awkward schoolgirl to a Hollywood life under the spotlight. Along the way she offers unfiltered insights into unwittingly courting controversy, curating a cautious but always authentic identity, and navigating the gap between private truth and public perception.

From the imagination stage to actually making the magic happen, writer-producer-actress Issa Rae is a multitasking phenomenon. She’s also an inveterate procrastinator. But even that’s part of her creative strategy. Blending personal anecdotes with practical insights, Issa explores the challenges of having to constantly deliver, the importance of “workations,” and the value of embracing a unique creative rhythm in an increasingly demanding world.

It’s a gamble to bet on yourself in Hollywood. But Issa Rae placed it. Charting her evolution from struggling writer to media mogul, she pulls back the curtain on her ever-evolving career in an always-changing industry and reveals that the best investment she made was her belief in herself. As she reflects on weathering storms and lessons learned, Issa moves forward with renewed purpose.