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I Should Be Smarter By Now #3

The Geography of Creativity

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What’s a West Coast girl with an East Coast vibe to do? In this reflective essay, New York Times bestselling author Issa Rae explores the universal search for a place to make her creative spirit come to life.

Issa Rae was born in Los Angeles but never felt she was quite the city’s type. Though each inspiration destination—from Potomac to Harlem—left its mark, Issa chases her dreams back to her sun-soaked roots. It’s there that Issa finally finds her voice, her wings, and the vibrant heartbeat of a creative community. Issa’s true muse had been waiting all along for her to come home.

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.

18 pages, Kindle Edition

Published August 26, 2025

126 people are currently reading
207 people want to read

About the author

Issa Rae

10 books1,155 followers
With her own unique flare and infectious sense of humor, Issa Rae’s content has garnered over 20 million views and close to 160,000 subscribers on YouTube. In addition to making the Forbes 30 Under 30 list twice and winning the 2012 Shorty Award for Best Web Show for her hit series “The Misadventures of Awkward Black Girl,” Issa Rae has worked on web content for Pharrell Williams, Tracey Edmonds and numerous others. She developed a TV series with Shonda Rhimes for ABC and is currently developing a half-hour comedy for HBO with Larry Wilmore. Rae is also slated to release a book of essays with Simon & Schuster in 2015.

Issa Rae is signed with UTA and 3 Arts Entertainment.

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5 stars
289 (49%)
4 stars
197 (33%)
3 stars
82 (14%)
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12 (2%)
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Displaying 1 - 30 of 49 reviews
Profile Image for Mai H..
1,362 reviews806 followers
September 2, 2025
It took me some time to love LA, but I do now. Issa is a LA native, but also spent time in her father's native Senegal. I greatly enjoy her episode on Antoni Porowski's show NO TASTE LIKE HOME. In fact, the entire series is great, but I digress.

Issa thought she had to move to NY to be a creative, but there are many creatives here. I love that she reads these. Her voice has the perfect cadence. Earth signs, you know.

🎧 Thank you to NetGalley and Amazon Original Stories
Profile Image for Keith Book Korner.
197 reviews33 followers
September 10, 2025
The story if if her life and her start in Hollywood.. Her narrating the audio just makes the book better to me..
Profile Image for The Bibliophile Doctor.
833 reviews285 followers
November 13, 2025
Book rating : 2 stars
Audiobook rating : 2.5 stars

The narration by Issa Rae herself was good. I have always found that narration by the author themselves is always better and spot on as they themselves know what thoughts they wanted to convey. This was better experience than reading the book.

First of all , I didn't know who Issa Rae is so I went in blindly in the book. As I got deeper into the book I had understanding who she is. I stay away from celebrity memoir for few reasons, mostly first is that I do not find their lives interesting. Second Almost everyone's struggles sound same. And third, they sound mostly self centred or self praising atleast.

Now I should be smarter by now wasn't exactly all that I mentioned but yet I didn't find it interesting. I was bored and wasn't interested what is happening. So I wasn't the right audience for this book. But then again I have read born a crime and enjoyed it thoroughly.

I requested it as it was amazon original and although writing is good, I didn't find the content funny or captivating.

Thank you netgalley and amazon original stories for the ARC in exchange of an honest review.
Profile Image for Shannon .
2,387 reviews160 followers
September 24, 2025
I Should Be Smarter by Now Collection


Source: Kindle Unlimited/Audible
Dates Read: 9/2/25 - 9/3/25
Average Stars: 4 Stars


The Business of Being Me - Issa Rae - 4 Stars - I did not know that Issa worked with Shonda Rhimes and Betsey Beers on a pilot, it actually sounded like a good show. I’m glad she said this lesson on conviction in your own talent.

Playing Well with Others - Issa Rae - 4 Stars - I love how she insists on running her writer’s rooms and set with respect. Not everyone will agree but no need to make anyone feel bad about it.

The Geography of Creativity - Issa Rae- 4 Stars - The “where” can be very important in creativity.

I See You Seeing Me - Issa Rae - 4 Stars - Embarrassment helps shape us.

The Art of Strategic Procrastination - Issa Rae - 4 Stars - I think I got the most out of this essay. Scheduling time to procrastinate when you know you are going to is illuminating. I realized I’ve been doing this for years as I regularly get up 20-30 minutes before I actually need to get up as I need that long to become human.

I Almost Know What I’m Doing - Issa Rae- 4 Stars - This title! Part reflection, part looking forward to the future. An admirable ending to the series.
Profile Image for Monique B..
189 reviews11 followers
October 6, 2025
This focuses on the importance of finding your "home" or place for growth & creativity.

I didn't realize Issa has lived on both the east & west coasts! Sometimes creativity is right where you are. Sometimes you have to journey to find where you are inspired the most

I loved hearing about all the ways Issa has given back to the place that inspired her the most - LA. This one was a more serious vibe than the previous 2.
Profile Image for Arianne.
112 reviews1 follower
September 11, 2025
This essay sprouted the thought for me of how representation matters, exposure matters. How much more likely people from someplace like LA or NY are to even conjure the idea of dreaming of being a creator because they are exposed to creators in their regular life. It’s a normalized idea, vs in a rural community such as my small town. When you ask kids what they want to do when they grow up and the answers are overwhelmingly teacher, nurse, police officer, etc things they are exposed to. If we’re never exposed to various topics and areas of study, how do we ever conjure the idea to dream about doing it? Finding and nurturing our talents? Just another example why museums, books, art, theater, etc are so vitally important to our society.
Profile Image for LaShanda Chamberlain.
613 reviews34 followers
August 25, 2025
I absolutely adore Issa Rae! From the moment I picked up The Misadventures of Awkward Black Girl, I was hooked by her humor, honesty, and unapologetic awkwardness that felt so real and relatable. In her latest collection, I Should Be Smarter By Now, Issa shares intimate insights into her journey to success—the denials, the challenges, and her creative process. Reading her words felt like sitting down with a close friend who’s not afraid to be vulnerable while inspiring you to keep pushing forward. Whether through writing, acting, or producing, Issa Rae’s work continues to celebrate culture, complexity, and connection, and this collection is no exception. I’m such a fan and will always show up for anything she creates! If you’re looking for an honest, uplifting read that blends humor with heartfelt wisdom, I highly recommend I Should Be Smarter By Now.

Thanks to NetGalley, the author & the publisher for the opportunity to read this advanced copy.
Profile Image for Adrienne Adrimano.
333 reviews5 followers
September 14, 2025
Notes about the places that inspire our creativity and finding a creative home, amidst a brief retelling of her cross-national temporary and permanent creative homes and people there
Profile Image for Ashley Jones.
29 reviews
December 30, 2025
Love & Basketball, at 16 had Issa transfixed as she watched Monica and Quincy fall in love around her neighborhood. Inspired, she wanted to create something that made others feel like that. Notable directors like Spike Lee and John Singleton inspired young filmmakers & storytellers. In 1994 when Issa was in the 4th grade, she finally had her own room and she discovered Notepad on the family computer that was kept in her room. She could write her own creations and print them! In 5th grade Issa casted her first role in a school play, although she was cast as a boy. She later joined a summer camp called Amazing Grace Conservatory, an acting program specifically for black kids run by Wendy Raquel Robinson who later was asked to play Issa Dee's mom on Insecure. At first Issa didn't feel a creative connection to LA and wanted to start her creative career in NY which lasted two years before she decided to move back home at 24. At this stage her creative collaborators were her high school friends and she began creating web series based around the talent of her friends. On January 26,2020 the day that Kobe & Gianna Bryant died from the helicopter crash, Issa was landing at the Los Angeles airport and heard for the first time her cheery voice over the intercom, "Welcome to Los Angeles....." as other passengers gathered around the TV to hear the news about Kobe. It was a bittersweet moment. "It was incredible to witness a city bonded by the loss of a figure they were so proud to have represent them." Issa became reminiscent of how LA had shaped her. "In that moment, I knew I wanted to make Los Angeles and the community that embraced my authentic self as proud of me as I was to call it home."
This entire review has been hidden because of spoilers.
Profile Image for Ivoree Malcom.
241 reviews2 followers
August 19, 2025
Sis had me at Love & Basketball!

Like Issa, I watched that film over & over again—memorizing lines, studying the emotion, feeling something awaken. That’s the thing about Issa Rae: she doesn’t just tell stories, she taps into the creative heartbeat we often forget to listen to. In The Geography of Creativity. Issa invites readers into her personal journey of discovering her own creative "home"—a space not just physical, but emotional & psychological, where ideas come easier, feel truer, & breathe more freely.

The book isn’t a rigid how-to guide. It’s more like a well-lit path through her own experiences, peppered with vulnerability & reflection. She shares what it looked like for her to find her creative habitat, & how that environment—be it a place, a mindset, or a community—became a catalyst for her authentic voice.

But here’s where the title really lingers: What if someone NEVER finds their creative home?

That question stays with you. Issa doesn’t claim to have all the answers, but her story gives hope that maybe “home” isn’t a fixed location or even a single identity—it’s a feeling, a rhythm, a resonance. Maybe it evolves as we do. Maybe it’s about listening to that inner spark & going wherever it leads, over & over again.

Whether you're in the middle of a creative breakthrough or stuck staring at the wall waiting for inspiration to strike, The Geography of Creativity might just be the nudge you need—or the mirror that reflects what’s already inside you.

*I received an advance review copy for free & I am leaving this review voluntarily.*

#ThankGodForARCs
Profile Image for Shoni Renee.
71 reviews1 follower
September 17, 2025
Issa Rae doesn’t just talk about creativity. She lives it. In this short but thoughtful essay, she reflects on what it means to find your creative “home” not a literal place, but a state of being where ideas feel natural, safe, and fully alive.

She walks you through her own journey of finding that space. For her, it wasn’t about chasing trends or following a formula. It was about paying attention to where her voice felt strongest and where her stories could breathe.

This isn’t a how to or a list of creative hacks. It’s a personal reflection. Issa shares memories, emotions, and setbacks. She opens the door to her process and gives you a chance to rethink your own.

One part stuck with me. She asks, what if someone never finds their creative home? It’s an honest question. And her answer doesn’t promise certainty. Instead, she reminds us that “home” might not be fixed. It might shift. It might follow you. It might be you.

And for the record, I don’t consider myself a creative person. Still, I found value here. Whether you’re full of ideas or feel completely blocked, this essay nudges you to pay attention to the spark inside. It encourages you to explore what places, people, or habits pull the best out of you.

The narration is excellent. Issa Rae brings warmth, humor, and a steady voice. Like the rest of her series, this was a quick listen that made me pause and think.

Rating: 4 stars

🎧 Thank you to NetGalley and Audible Studios for the advance listening copy.
1,203 reviews8 followers
October 8, 2025
This chapter of the essay is very much just a memoir of her personal journey. She reminds creatives that your mindset, community, and influences ground your projects. It’s important to find a place that feels safe and supportive. To honor them is to be authentic to yourself, but these evolve over time. It’s true and fine, but variable for everyone.
* * * * * * * * * * * * * *
Issa Rae was born in LA but didn’t feel tethered to the Hollywood scene. Yet struggled after moving to New York and surrounding herself with East Coast creators. She even questioned if her small budget could be put to better use in a place like Senegal. Rae found her creative process wasn’t about chasing trends or adhering to formulas. When she returned home and accepted that each of these places—Harlem, Palo Alto, Potomac—had influenced her dreams and style, things become easier. Her creative home wasn’t a physical location. Now she strives for authenticity and supportive efforts for those that aided her and those that will follow.
This entire review has been hidden because of spoilers.
Profile Image for January.
2,884 reviews126 followers
August 28, 2025
The Geography of Creativity by Issa Rae (2025)
I Should Be Smarter By Now #3
18-page Kindle Ebook story pages 5-17

Genre: Nonfiction, Memoir, Essays, Short Stories, Business

Featuring: Amazon Originals, Los Angeles, California; Maryland, Senegal, New York City, New York; Acting, Childhood Dreams

Rating as a movie: PG-13

Songs for the soundtrack: IGOR by Tyler, the Creator, Nipsey Hussle

Books and Authors mentioned: Love & Basketball by Gina Prince-Bythewood, Boyz in the Hood by John Singleton, Do the Right Thing by Spike Lee, Midsummer Night's Dream by William Shakespeare

My rating: ⭐️⭐️⭐️½🎭🎬🎥

My thoughts: This was a nice story.

Recommend to others: Yes.

I Should Be Smarter By Now
1. The Business of Being Me
2. Playing Well with Others
3. The Geography of Creativity
4. I See You Seeing Me
5. The Art of Strategic Procrastination
6. I Almost Know What I'm Doing
Profile Image for Rae Quigley.
368 reviews18 followers
August 27, 2025
I’ve been a fan of Issa Rae for several years, and she definitely shines in her writing. Listening to this as an audiobook felt like being on a phone call with a friend. She tells her stories in ways that feel relatable, and prove to be authentic.

This one in particular really resonated with me. I have always been a creative person, and always wanted to work in entertainment. I moved from city to city chasing creativity and the freedom I thought I would get in each place, so sure that the location would end up being the key.

These are super quick reads, and the entire collection as a whole is enjoyable. Issa does a fantastic job as a narrator, and the stories have humor while maintaining a strong lesson.

Thank you NetGalley, Brilliance Publishing and Amazon Original Stories for sending this audiobook for review consideration. All opinions are my own.
Profile Image for Miss Kitten’s Corner.
291 reviews16 followers
August 24, 2025
Thank you so much to Amazon Original Stories and Netgalley for providing me an advanced audiobook copy of this book.

In this one Issa talks about how she was trying to find the perfect town to settle into that will help her craft and inspire her work, but at the end she learns that it's not just the place, it's the people around you that actually helps and lift you into your craft.

This is my least favorite because it's the shortest one of the bunch so I think there could have been more to tell here. But it was still inspiring all the same.

And as always Issa did an amazing job narrating her own book. I love how she delivers her message and lines. Highly recommend!
Profile Image for Mahoghani 23.
1,338 reviews
October 8, 2025
Inspiring

A poignant narrative exploring the resilience of the human spirit, this memoir delves into the transformative journey of a passionate individual navigating life's challenges. Through a blend of humor and raw emotion, the story illuminates the power of friendship, unwavering determination, and personal growth in the face of seemingly insurmountable obstacles. Each setback becomes a stepping stone, revealing profound insights and the extraordinary strength that emerges when one refuses to surrender to adversity.
Profile Image for Donttouchmypoodle✨.
127 reviews2 followers
October 31, 2025
Huge Issa fan, so when I saw these 6 short stories were available, I jumped on them! I listened to the audiobooks and loved that they were narrated by Issa herself. I’ve read her first memoir, The Misadventures of Awkward Black Girl, so I knew I’d get that same personality and humor while reading/listening to The Business of Me collection. Every book was an easy 5 star read for me. My only disappointment was the use of AI generated cover art 🫠 It seemed a jarring choice considering Issa’s reputation as a creative and advocate for the arts.
39 reviews
November 21, 2025
I grew up watching and learning from Issa Rae. This collection of essays adds history and context to the many successful projects I have enjoyed from her over the years. I really liked the way she infused humor into each essay and concluded them with a thought-provoking statement that can apply to the life of anyone, not just a creative. From the importance of work ethic and how to use it to how she turned her mistakes into success, there is something in here for anyone looking for motivation and inspiration. Thank you to NetGalley and Amazon Original Stories for a copy of this collection!
656 reviews
October 9, 2025
Each of these "books" is actually just an essay. I wish I could rate them and record having read them as one, but this will have to do. I was not familiar with this actress/showrunner/writer prior to reading these, so some may be lost in translation. I do want to go back and check out her first book though, as these were light, easy essays with some humor and good storytelling. They just were short essays, so couldn't really go in depth into any one thing.
Profile Image for Rachel.
55 reviews1 follower
October 12, 2025
This book is part of a 6-themed series where Issa Rae peels back the curtain to her creative process and the lessons she's learned over her 20 years making TV/film. It is a rare glimpse from a Black POV. If you're doing a MFA (Masters in Fine Arts) or if you are self-taught via Youtube University, this is a must-read for any aspiring creative. Especially POC. I listened to the audiobook, which Issa Rae narrates herself. Bonus: she pronounces French words correctly!

[Thanks to NetGalley for the Advanced Reader Copy]
Profile Image for Bre.
80 reviews1 follower
August 22, 2025
I've been a fan of Issa Rae for years, my first introduction to her was the show Insecure and she carries that same comedic upbeat energy into this collection of essays. Her reflections are inspiring.

Listening to the audiobook (narrated by Issa herself) felt like yapping with a friend—funny, thoughtful, and candid.

Huge thanks to NetGalley, Brilliance Audio, and Issa Rae for the ALC!
Profile Image for Tiffany.
42 reviews1 follower
September 3, 2025
I loved this collection of stories so much! If you loved the show Insecure, then you will love these stories.

Thank you to NetGalley for allowing me to read this book in exchange for my honest review.
Profile Image for Tanesha Abernathy.
520 reviews1 follower
September 9, 2025
I am enjoying this series…being as though I’m reading out of order. It’s good to hear other perspectives of how they view themselves, their surroundings and how it affects their creativity.

I can agree with a lot said in this series.
Profile Image for Bruce Dinsman.
1,554 reviews3 followers
September 10, 2025
Immersed!

Wow, I got so into the where, who, and what that this little essay didn’t make it through my fist cup of coffee. Thanks for a good look at your world Issa. I hear that, shows involving Las Vegas never get it right. Sorry, but once again a one-star ding for language
3 reviews
September 15, 2025
Finding Home

I love the pride she has for LA and how connected she has always felt even with each move she has made in her life from childhood to adulthood. A relatable writer for sure.
Profile Image for ChloeShondra Robertson.
173 reviews3 followers
November 25, 2025
Issa speaks on wanted to be an actress at a young age. She attended a School ran by Wendy Raquel Robinson which later cast her as her mother in her show Insecure. Mainly she speak on how she started in Hollywood.
2 reviews
December 2, 2025
Finding Your Creative Home

Issa Rae invites me to review my creative journey so far and the nomadic nature of my own inspiration. Where do I feel most home creatively? Which setting, place, and people helped me to blossom creatively?
Displaying 1 - 30 of 49 reviews

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