I Almost Know What I'm Doing

I Should Be Smarter By Now

By: Issa Rae

Narrated by: Issa Rae

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.

©2025 by Issa Rae. (P)2025 Brilliance Publishing, Inc., all rights reserved.

The brilliance of being me..

I loved that she was so transparent about her journey. She’s such a great creative and Insecure will always be a favorite of mine.

Love the honesty

This speaks to me… so glad she put this out. Easy to listen to and to the point. Narrative, necessary for listen ability and kept short and sweet.

Issa's humor and transparency

I love that it was straight forward and informative. She was honest and took accountability for her mistakes & losses.