The Business of Being Me: I Should Be Smarter By Now

I Should Be Smarter By Now #7

by Issa Rae

A funny and inspiring essay about ambition, persistence, self-discovery, and the thrilling—if unpredictable—business of creativity by Issa Rae, one of Hollywood’s most innovative voices.

Even at seven years old, Issa Rae meant business, conducting herself with entrepreneurial authority on a toy phone in her bedroom. Eventually, it was a matter of convincing others that she had a lot to say and getting them to listen. From her first web series, Awkward Black Girl, to network disappointments to HBO triumphs, Issa charts her aspirational journey—self-doubts and all—of being taken seriously, finding her voice, and shaping it into a groundbreaking career.

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.

Genres: Audiobook, Short Stories, Nonfiction, Memoir, Biography, African American

Audible Audio

Published August 26, 2025

About the author

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.

Reviews

[Mai H. · Rating 4 out of 5]

Made better by her own narration, Issa is both funny and relatable. I knew she was a Capricorn before she even said so. That "I Hate LA Dudes" podcast that isn't quite a podcast? I feel that.

🎧 Thank you to NetGalley and Amazon Original Stories

[Keith Book Korner · Rating 3 out of 5]

Great story about how she started in the business
The audio is great because she delivers the story
Which makes the experience better

[MJ · Rating 5 out of 5]

I enjoyed this collection of essays. Issa Rae writes in a way that is entertaining, comedic and informative. I couldn’t relate to the topics at hand, however I still enjoyed what she had to say and the delivery.

[Sihle 🪻🌸🌷🌼🌝 · Rating 5 out of 5]

“All I had to do was want it, work hard on it, and have it.” 🤏🏽🤏🏽period

Insecure is literally my number one favourite show, so I’ve always been fascinated by Issa Rae’s journey. Reading The Business of Being Me gave me even more insight into how much work, resilience, and persistence goes into her success. It’s easy to see her achievements on screen and assume it all came naturally, but this book shows the behind-the-scenes reality, how she navigated setbacks, learned from failures, and kept pushing forward. That combination of hard work and determination is what makes her so inspiring.

I’m not the biggest fan of the covers, but honestly, that doesn’t matter because the content is what counts. Everyone should read this book, it’s motivating, honest, and shows the real grind behind the glamour. Issa’s journey makes you believe that with passion and persistence, you really can carve your own path.

[Shae · Rating 5 out of 5]

Rtc

[Ivoree Malcom · Rating 3 out of 5]

The Business of Being Me by Issa Rae felt more like a resume in memoir form than an engaging narrative. I couldn’t shake the feeling that I had no business reading this—like I was eavesdropping on a journey that, while personal, lacked the emotional or storytelling punch to make it compelling to outsiders.

The storyline moves predictably: a 7-year-old working pretend fast food, then morphing into a high school writer, & eventually becoming a successful adult with a TV pilot under her belt. It’s all neatly laid out, but that’s also the problem—it feels like bullet points instead of moments. While it’s commendable to see someone’s growth documented, the pacing & delivery didn’t offer much to latch onto emotionally or creatively.

There are glimpses of humor & intelligence, which you'd expect from Issa Rae, but they’re too few & far between to carry the book. I kept waiting for a moment that would surprise me, make me feel something, or reveal a deeper layer—and it never quite came.

Maybe it’s just me, but this one didn’t land.

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

#ThankGodForARCs

[Monique B. · Rating 4 out of 5]

I love Issa! I do recommend the audiobook for this since she is the narrator. A quick & short read!

This one focuses on her first steps into the entertainment world & how unpredictable everything was (is). I did learn a few things about her.

[Aisha · Rating 4 out of 5]

The set is such an easy read! I like reading about how she got to where she is and things she does to maintain.

[Shannon · Rating 4 out of 5]

I Should Be Smarter by Now Collection


Source: Kindle Unlimited/Audible
Dates Read: 9/2/25 - 9//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.

[Kim Catanzarite · Rating 5 out of 5]

I'm a fan of Issa Rae, and I watched her Insecure series, which was great, so it was really interesting to see how it came about. Funny how we often don't consider the struggles a creative person goes through before accomplishing their goals and become well-known. She's very candid about how she began her career and how hard it was to get a TV series off the ground. I'll be listening to other parts of this Audible series.

[Bianca | bookd_by_bee · Rating 5 out of 5]

Thank you to NetGalley & Brilliance Publishing for the ALC! All thoughts and opinions are my own.

As a huge fan of her show “Insecure” on HBO, I was so excited to be given the opportunity to review Issa Rae’s newest essay series “I Should Be Smarter by Now” for Amazon.

This is the first in a series of 6 parts and details her early endeavors in breaking into the entertainment space out in Hollywood. I enjoyed listening to Issa describe her journey and how she put her unique spin on her experiences. She uses humor and insight to discuss how the path to success isn’t linear and that every closed door can also be turned into a lesson. By staying true to herself, and being open to collaboration and new experiences, she was able to successfully pitch her pilot which would ultimately become the smash hit “Insecure” (which still remains my emotional support show).

This is my first experience listening to a series in this format and I have to say I really enjoyed it. With the shortening attention spans of everyone in our society, I found it easy to listen to this essay as I was multitasking in the background and not getting distracted. I’m excited to listen to the entire series and look forward to hearing more about her inspiring journey in entertainment.

[BookBabe · Rating 4 out of 5]

I felt like the essay was an honest glimpse into the less glamorous aspects of the creative journey.

“It was my first painful lesson that in this business, work ethic alone isn’t currency—you have to be savvy with where and how you spend your efforts.” - Issa Rae

[Jennifer · Rating 4 out of 5]

Issa is one of my favorite creatures and exciting to learn more about her process. Very interesting read .

[Coleen · Rating 4 out of 5]

I love when successful people share insights into how they got where they are. Issa Rae is a true Capricorn.

[Charell · Rating 5 out of 5]

Audiobook Review: The Business of Being Me
by Issa Rae | Narrated by Issa Rae

Issa Rae is hilarious and refreshingly authentic in this essay. I love how she shares her journey in a way that feels both inspiring and down-to-earth, reminding creatives like me to show up fully as ourselves. Her reflections on persistence and navigating feedback (“notes”) were especially encouraging—sometimes a “no” isn’t the end, and our ideas are still worth exploring.

This essay left me motivated to take more chances with my own creativity, and I’m excited to dive into the next one. Hearing it in Issa’s own voice made it even better—like getting advice from a witty, wise friend.

⭐️⭐️⭐️⭐️⭐️

Thank you to NetGalley and the publisher for the advanced listener copy in exchange for my honest review.

[Mahoghani 23 · Rating 4 out of 5]

Heartfelt

An intimate glimpse into the author's journey, revealing the raw challenges of navigating the competitive television pilot landscape. Her candid narrative exposes personal vulnerabilities while highlighting remarkable resilience, demonstrating how self-reflection and determination can transform setbacks into stepping stones toward creative success.

[Reader · Rating 4 out of 5]

I thoroughly enjoyed The Business of Being Me by Issa Rae. As a longtime fan, I loved gaining insight into the inner workings of her creativity and brilliance. What made it even more inspiring was seeing how she uncovered things about herself and her journey that she hadn’t even fully realized while navigating the business world. It felt honest, refreshing, and motivating—like getting a front-row seat to both her wins and her lessons.

[Bre · Rating 4 out of 5]

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!

[Adrienne Adrimano · Rating 3 out of 5]

Good insight into the screenwriting process and industry in the USA and how Awkward Black Girl (web series) and Insecure (HBO series) came to be

[M.C. Walker · Rating 5 out of 5]

Lesson learned

I enjoyed learning about Issa's road to success! This was the creative inspiration I needed to keep going in life

[Mae B · Rating 5 out of 5]

Always love every thing Issa Rae. This was a nice summary of her journey and the BTS of the entertainment industry. Never really understood how much they go through to get shows green lit.

[Veronika]

Ran to Goodreads when I saw that Issa Rae pulled a Beyoncé and is surprise dropping a new book and just announced an upcoming book tour. Wow, I’m excited for this book/book series. I hope it doesn’t stay a Kindle exclusive though.

[January · Rating 4 out of 5]

The Business of Being Me by Issa Rae (2025)
I Should Be Smarter By Now #1
22-page Kindle Ebook story pages 5-21

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

Featuring: Childhood Memories, Business Sense, Dramatic Play, School, Television Shows, Perseverance

Rating as a movie: PG-15/R for adult themes

Books and Authors mentioned: The Misadventures of Awkward Black Girl by Issa Rae

My rating: ⭐️⭐️⭐️⭐️💼

My thoughts: This was very insightful, it is certainly more memoir than business or self help.

Recommend to others: Yes, this was insightful and shorter than expected.

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

Memorable Quotes: While the other endeavors lasted a year or less, writing for the newspaper stuck. In addition to writing traditionally “serious” articles for our publication, I started my own column called How ’Bout You Don’t, where I was critical of the habits, culture, and fashion of our student body and faculty. How ’bout you don’t keep volunteering to read out loud when you know you can’t read? My raw candor made me an occasional target of hallway stares and almost got me beat up a few times, but generally people valued and saw the humor in what I wrote. Writing was my new outlet—a way of convincing others that I had something to say.

From imaginary hamburger orders to ABC disappointments to HBO triumphs, each experience taught me something critical about the business of creativity. What began as a childhood understanding of “serious business” evolved into something much more nuanced: the knowledge that success in creative industries requires more than just hard work. It demands resilience after rejection, the confidence to preserve your voice amid conflicting feedback, and the wisdom to distinguish between being a team player and being the captain of your own creative ship. Most importantly, I learned that making writing my business meant treating it as such—being strategic about opportunities, valuing my contributions appropriately, and ultimately believing that my perspective was worth putting in that briefcase I’d wanted since I was seven years old.

[The Bibliophile Doctor · Rating 2 out of 5]

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.

[Shoni Renee · Rating 4 out of 5]

This first installment in Issa Rae’s essay series takes you back to her early days in Los Angeles, before the hit shows, before the red carpets. She unpacks what it meant to chase her vision in an industry that wasn’t exactly waiting to welcome her in.

Issa doesn’t sugarcoat the grind. Through wit and honesty, she paints a clear picture of what it took to make her voice heard. She talks about failure, doubt, and how she kept moving anyway. Every misstep became part of the plan. Her perspective is smart, funny, and all her own.

As someone who’s always admired her work, especially Insecure, this audiobook pulled back the curtain on what it took to get there. Her storytelling is personal without being overly polished. You hear the hustle. You feel the lessons. And because Issa narrates it herself, it’s like getting the inside scoop from a close friend who made it and still remembers exactly how it felt to be on the outside.

Big thanks to NetGalley and Brilliant Audio for the advanced listening copy.

[Talia Smith · Rating 5 out of 5]

Issa Rae Shows That Authenticity Is Still Her Superpower


Issa Rae’s The Business of Being Me is more than a comedy special — it’s an honest reflection on identity, ambition, and authenticity. Issa blends humor with hard truths, exploring what it means to be a Black woman navigating success in Hollywood without losing herself in the process.

What stands out most is her vulnerability. She doesn’t hide behind her usual awkward charm; instead, she uses it to open doors to deeper conversations about self-worth, imposter syndrome, and the cost of “making it.” It’s smart, relatable, and deeply human.

The writing is sharp and self-aware, filled with moments that make you laugh and then pause. By the end, The Business of Being Me feels less like a performance and more like a mirror — a reminder that being yourself is both the hardest and most powerful business decision you can make.

[Megan Collins · Rating 2 out of 5]

Personal essays are always hard to rate. Issa Rae describes her career in Hollywood as a writer, actress, producer, and author. I don’t personally relate to those professions and so the inspiration to maintain towards her goals feels flat. She narrates it herself which is always a plus, There are rare moments of wider self-reflection regarding self-doubt, finding your own voice, and accepting a future different from your imaginings but only in a glancing acknowledgement.
* * * * * * * * * * * * * *
Childhood dreams of attaché briefcases and big business shifted over time to visions of self-expression. It then looks at her first web Series, Awkward Black Girl, and how she was still undervaluing herself. Then she chronicles the failure of securing her first television pilot and how things went differently with HBO’s Insecure.

[LaShanda Chamberlain · Rating 5 out of 5]

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.

[Miss Kitten’s Corner · Rating 4 out of 5]

Thank you soooo much to Amazon Original Stories Publishing and Netgalley for providing me an advanced audiobook copy of this book.

I loved how Issa narrated her own book. This was short and sweet and it gave me insight on her life about how she never gave up and didn't stop being herself.

She gave her raw feelings of how she was feeling stuck and envied her new found friend and partner of a project they were suppose to do together. They were moving on to bigger and better things while nothing was happening with her life.

A beautiful beginning to a new chapter in her life that everyone should take the time out to read this in their life.

[Turesa Lewis · Rating 4 out of 5]

Great Story

I liked that she shared her story and how it all happened. The inside information of the writing process is exhilarating yet gruesome. I am glad to learn the process. I also liked that she shared where her ideas came from. Now I understand the episodes of the show. I also appreciate her writing style which is to the point. Breaking this up into six pieces makes it an easy quick read. This book isn't just about being in business; it's about how conduct business. As a business owner you are expected to write a business plan which provides the blueprint for the business. This explains the inside of the business and how to get it moving.