Issa Rae Shares Hard-Won Hollywood Wisdom in Upcoming Book 'I Should Be Smarter Now'
Issa Rae Shares Hard-Won Hollywood Wisdom in Upcoming Book 'I Should Be Smarter Now'

Published: June 6, 2025

Get ready for a dose of Hollywood wisdom from Issa Rae, as she releases her second essay collection, 'I Should Be Smarter Now', on August 26. The book is a follow-up to her first essay collection, 'The Misadventures of Awkward Black Girl', and is published under Amazon Original Stories. Rae, 40, will delve into the behind-the-scenes of building her creative empire, staying true to her vision while navigating Hollywood's ups and downs.

"This collection is part confession, part reflection, and part 'here's what I wish I'd known'," Rae exclusively tells PEOPLE. "But mostly it's just me being honest about the weird, wonderful journey from having big dreams to making them a reality."

The collection includes six individually published essays on a range of topics, including "The Business of Being Me", "Playing Well with Others", "The Geography of Creativity", "I See You Seeing Me", "The Art of Strategic Procrastination", and "I Almost Know What I'm Doing".

In the essays, Rae reflects on her childhood, her hometown of Los Angeles, and her gradual realization that it was her true muse. She also shares her journey from being an awkward schoolgirl to a Hollywood life under the spotlight, and how she has become a multitasking phenomenon in her personal and professional life.

The collection concludes with an aptly titled essay, "I Almost Know What I'm Doing", where Rae reveals that the best investment she made was her belief in herself.

'I Should Be Smarter Now' is available for preorder now and will be released on August 26.

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