Playing Well with Others

I Should Be Smarter By Now

By: Issa Rae

Narrated by: Issa Rae

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.

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

Love Issa

I love listening to Issa's journey to writing. I have so many stories that I want to write but this gives me a guide and confidence to do it.

This one’s pretty funny and a good lesson

I read this in particular because evidently this is something I need to do better. There’s a mix between working to keep your vision and working with people and politics, and Issa goes over her trials and tribulations with it very well.

I love how she tells her stories

I could definitely relate to this book. As I am trying to get it if my shell, stand by my beliefs and work well with others, it was interesting to hear another perspective. I, also, tend to be very particular, but I've learnt to be open minded and learn from others because they might see gaps where I dont

Very insightful

I love this because anyone can gain valuable insights from Issa’s experiences. I highly recommend everyone.