Playing Well with Others

A refreshingly candid essay about artistic integrity, maintaining creative authorship, and being collaborative to the max by Issa Rae, writer, producer, and star of HBO’s award-winning Insecure.

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.

From writer, actress, producer, and New York Times bestselling author Issa Rae comes I Should Be Smarter by Now. In these essays, she shares her journey from internet creative to a multi-hyphenate career in Hollywood. Read or listen to them in a single sitting. Either way, they’re insightful, hilarious, and unapologetically authentic.