I Almost Know What I'm Doing

A fearlessly authentic essay about the entertainment industry—the setbacks, high-stakes risks, and hard-won successes—by Issa Rae, named one of Time magazine’s most influential people in the 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.

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.