I Should Be Smarter by Now

In this comically insightful collection, Issa Rae charts her journey from digital storyteller to cultural force, redefining modern success. Through refreshingly candid essays, she takes readers behind the scenes of building her creative empire, sharing hard-won wisdom about staying true to your vision while navigating Hollywood’s ups and downs. It’s a master class in turning authenticity into achievement.

The Business of Being Me

In this funny and inspiring essay about ambition, persistence, self-discovery, and the thrilling—if unpredictable—business of creativity, Issa Rae charts her aspirational journey of finding her voice and shaping it into a groundbreaking career.

Playing Well with Others

Independent spirit Issa Rae explores the superpower of collaboration while remaining unapologetically herself in this refreshingly candid essay about artistic integrity and maintaining creative authorship.

The Geography of Creativity

In this reflective essay, New York Times bestselling author Issa Rae chronicles her journey as a West Coast girl with an East Coast vibe, exploring creative inspiration from Potomac to Harlem before discovering that her true artistic voice and vibrant community were waiting in her sun-soaked Los Angeles roots all along.

I See You Seeing Me

From mortifying teenage moments to Hollywood stardom, award-winning creator Issa Rae pens a witty essay on identity, fame, and unwavering authenticity in a world that’s always watching.

The Art of Strategic Procrastination

With her trademark humor and unflinching honesty, Issa Rae delivers an insightful essay on finding balance in Hollywood’s high-stakes hustle culture, exploring everything from “workations” to the surprising benefits of her own creative delays.

I Almost Know What I’m Doing

Issa Rae pulls back the curtain on the ultimate Hollywood gamble—betting on yourself—as she reflects on her evolution from struggling writer to media mogul, revealing how trusting her own vision became her best investment.