🎬 Book Review: Playing Well with Others by Issa Rae (Kindle Edition, I Should Be Smarter By Now Series)
A candid, funny, and insightful essay on collaboration, creative control, and the art of working with others—Issa Rae reflects on her evolution from solo creator to Hollywood multi-hyphenate with grace and grit.
🧠 Overview
Published as Book 2 in the I Should Be Smarter By Now series, Playing Well with Others is a 22-page Kindle Original by Issa Rae, the Emmy-nominated creator of Insecure and bestselling author of The Misadventures of Awkward Black Girl. In this essay, Rae explores her journey from fiercely independent content creator to someone who’s learned to embrace collaboration—without compromising her vision.
From writers’ rooms to blockbuster film sets (including Barbie), Rae shares how she navigated the tension between maintaining creative authorship and trusting others to elevate her work.
✨ Key Themes & Highlights
- 🎭 Creative control vs. collaboration: Rae discusses how letting go of full control doesn’t mean losing your voice—it can amplify it
- 💼 Hollywood dynamics: Offers behind-the-scenes glimpses into how projects get made, and how personalities shape outcomes
- 🧠 Personal growth: Rae reflects on her early resistance to teamwork and how she learned to build trust with carefully chosen allies
- 💬 Signature wit: The essay is packed with Rae’s trademark humor, sharp observations, and unapologetic authenticity
“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.” — Goodreads summary
💬 Reader Reception
- ⭐ Goodreads rating: 4.54/5 from early reviews
- 📖 Readers praise the essay’s honesty, humor, and relatable insights into creative life
- 🧾 Many found it empowering, especially for women navigating leadership roles in collaborative environments
- 💬 “A refreshingly candid essay about artistic integrity and being collaborative to the max.” — Goodreads reviewer
⚠️ Considerations
- 📄 Short format: At 22 pages, it’s a quick read—best enjoyed as a thoughtful vignette rather than a deep dive
- 📚 Part of a series: Works well as a standalone, but even better when read alongside other essays in I Should Be Smarter By Now
- 🧾 Best for creatives: Especially resonant for writers, producers, and anyone balancing vision with teamwork
🏁 Final Verdict
Playing Well with Others is a smart, funny, and empowering essay that captures Issa Rae’s evolution as a creator and collaborator. It’s a must-read for anyone navigating the creative industries—or simply learning how to work well with others while staying true to themselves.
