🎭 Book Review: I Almost Know What I’m Doing by Issa Rae (Kindle Edition)
A candid, witty, and refreshingly honest essay from one of Hollywood’s most dynamic voices—offering insight into the creative chaos, self-doubt, and triumphs behind the scenes.
🧠 Overview
Published in August 2025 as part of the I Should Be Smarter By Now essay collection, I Almost Know What I’m Doing is a short, unfiltered reflection by Issa Rae, the Emmy-nominated creator of Insecure and founder of HOORAE Media. This installment charts her evolution from internet creative to media mogul, focusing on the uncertainty and improvisation that often define success in Hollywood.
Delivered in Rae’s signature voice—equal parts sharp, self-aware, and hilarious—the essay explores the high-stakes risks, career pivots, and emotional resilience required to thrive in an industry that rarely offers clear direction.
✨ Key Themes
- 🎬 Betting on yourself: Rae reflects on the gamble of trusting her own vision in a system built to doubt it
- 🧠 Imposter syndrome & growth: She shares how self-doubt coexists with ambition, and how she’s learned to navigate both
- 💼 Behind-the-scenes hustle: From awkward meetings to unexpected wins, Rae pulls back the curtain on her creative journey
- 😂 Humor as armor: Her comedic lens makes even the most vulnerable moments feel empowering
This essay is part of a six-piece series, each one offering a different facet of Rae’s personal and professional life, with titles like The Business of Being Me and I See You Seeing Me.
💬 Reader Reception
- ⭐ Amazon and Audible ratings: Highly positive
- 🎧 Available as both a Kindle read and an Audible Original, narrated by Issa Rae herself
- 📖 Readers and listeners praise its authenticity, relatability, and sharp humor
- 🧾 Especially resonant for creatives, entrepreneurs, and anyone navigating uncertain career paths
“It’s a gamble to bet on yourself in Hollywood. But Issa Rae placed it.” — Amazon Original Stories
⚠️ Considerations
- 📄 Short format: At just under 30 minutes in audio, it’s a quick but impactful read
- 📚 Best appreciated in context: Works well as part of the full I Should Be Smarter By Now series
- 🧾 Not a traditional memoir: It’s more of a snapshot than a comprehensive life story
🏁 Final Verdict
I Almost Know What I’m Doing is a funny, fearless, and deeply human essay that captures the messy brilliance of Issa Rae’s creative path. Whether you’re a fan of her work or simply seeking inspiration from someone who’s still figuring it out—while thriving—this Kindle edition is a smart, soulful read.
