Playing Well with Others

I Should Be Smarter By Now #2

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.

Genres: Audiobook, Short Stories, Nonfiction, Essays, Ebooks

22 pages, Kindle Edition

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 3 out of 5]

From one Earth sign to another, being particular is chef's kiss. Also enjoyed the bits from the BARBIE movie. Iconic.

🎧 Thank you to NetGalley and Amazon Original Stories

[Sihle 🪻🌸🌷🌼🌝 · Rating 5 out of 5]

I fear I’ll be coming back to read these stories every month, they’re just that amazing! Each one feels like a reminder of why passion and purpose matter so much. As someone who usually dreads collaborative work but is still deeply committed to what I do, this piece felt both essential and necessary. It challenged me to see collaboration in a new light, not as something that takes away from individuality, but as something that can strengthen and elevate it.

“Creativity thrives when we lean into our authenticity and share the process with those who enhance our work.” That line really stayed with me, it’s a beautiful reminder that we don’t lose ourselves when we create with others, we actually expand.

[Keith Book Korner · Rating 3 out of 5]

The series is just getting better.. The audiobook is truly the best her being the narrator just enhanced the experience

[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.

[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.

[Jae Philon · Rating 4 out of 5]

You dont have to do it alone!

My take away from this well written short…Being Black and a Woman we tend to feel like we HAVE to do things on our own. Especially in creative spaces. Its like once we feel assistance is needed its no longer “ours” and it it becomes a disappointing failure when thats not actually the case. We should lean into our resources more, play the game with a team, we shouldn’t have to do it all alone.

[Ivoree Malcom · Rating 5 out of 5]

Playing Well with Others is a refreshing & insightful exploration of the power of collaboration & how much it can elevate our creative potential. Issa Rae brilliantly outlines how working with others—when done with openness, humility, & intention—can lead to outcomes far greater than what we could accomplish alone.

What I especially love about Issa’s approach is her emphasis on being receptive to feedback & criticism. She doesn’t present collaboration as blindly following the crowd but instead encourages finding that healthy balance between staying true to your vision & being flexible enough to adapt. That balance, she argues, is a true superpower—& I couldn’t agree more.

Issa’s ability to frame collaboration not just as a skill, but as an energy we can lean into, really resonated with me. Whether you’re helping fulfill someone else’s vision or bringing your own ideas to life, being part of something bigger—while still honoring your own voice—is an experience that can transform your work & your mindset.

This title is a reminder that creativity doesn't have to be solitary, & often, it's at its best when shared. A must-read for artists, creatives, & anyone looking to grow through meaningful connection.

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

#ThankGodForARCs

[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 so much to Amazon Original Stories and Netgalley for providing me an advanced audiobook copy of this book.

I really liked this one because Issa talks about how she would take other people's opinions about her work and how she learned to take criticism. She also learned how to use other people's opinions of her ideas to improve her work.

I really loved how she also told a story about how she was working with someone in particular that not only made Issa uncomfortable but also one of her other co-workers uncomfortable and how she handled the situation and how she could have handled it better.

And as always she did an amazing job narrating! Highly recommend! One of the many books to read in your lifetime.

[Monique B. · Rating 4 out of 5]

This one was funny & relatable. Girl, I've hated group projects since middle school too and would rather do it myself! But yet...

Issa breaks down how getting input/feedback from others and having a crew who also sees your vision is key in the entertainment industry. Trying to do it all can actually set you back. Other gems were dropped in Issa form 🤭

*Currently looking up other projects she's been involved with due to the little tea spilled* ☕

[Greyson · Rating 5 out of 5]

4.5⭐️ “Nobody but nobody can make it on their own” explained. I related to Issa Rae so much in this Essay cause I do not work well with others and that has bit me in the backside a couple times. I appreciate this transparency. It’s okay to be “particular” and honor your vision. Standing up for yourself and your integrity. This was great!

[Ntombezinhle Nzama · Rating 5 out of 5]

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

[Shae · Rating 5 out of 5]

Rtc

[Shoni Renee · Rating 3 out of 5]

Issa Rae’s Playing Well with Others unpacks the benefits and challenges of working with people creatively. It’s a short, thoughtful listen that highlights how collaboration done with clear boundaries and the right mindset can push your work forward.

She shares personal examples and industry takeaways, including a touching moment from her time on the Barbie set that shows how meaningful teamwork can be. One of the strongest points she makes is about the value of feedback. Issa doesn’t sugarcoat it she admits it isn’t always easy to take but she argues it’s necessary for growth. I respect that honesty.

The audiobook emphasizes the importance of knowing when to lead, when to support, and when to adjust. It’s not a groundbreaking essay, but it’s a solid reminder for creatives who want to be more intentional about how they show up in group settings.

Some parts felt repetitive or underdeveloped, which is why this landed as a three-star for me. Still, it’s worth a listen if you’re navigating group dynamics in a creative field.

Thank you to NetGalley and Brilliant Audio for the advance listening copy.

[FictionalFlings · Rating 5 out of 5]

I love the thoughts and insight of Issa Rae. Raw and honest.

[SweetLorraine · Rating 4 out of 5]

I like the lesson(s) that Issa shared in this series. There definitely value in playing well with others.

[Shauntelle (shauntellereads) · Rating 4 out of 5]

This audiobook was a quick but powerful listen. Issa Rae breaks down the reality of working with others in creative spaces, especially as a Black woman, where we’re often taught to prove we can do everything by ourselves. Her message hit home: collaboration isn’t a weakness, it’s a skill, and sometimes the smartest move you can make is to share the load.

I loved how she talked about running sets and writers’ rooms with respect and intention. It’s not about everyone agreeing, it’s about allowing people to show up and contribute without feeling small. That’s leadership.

What stood out most was her take on feedback, not as a threat to your vision, but as something that can elevate it. I definitely needed that reminder.

My only wish? That it was longer. I would’ve loved more examples and stories, because Issa’s perspective is always sharp and refreshing.

Thank you NetGalley and Brilliance Publishing and Amazon Original Stories for the ALC in exchange for the honest review.

[Ashley Jones · Rating 4 out of 5]

Issa is real particular, but only when it comes to work....or hotels or choosing a restaurant. Particular in that Issa likes things a certain way. At the beginning of her career she definitely felt the need to do it all, to earn all the credit to show people this was her work and she was capable. This resulted in years of operating at an inefficient level as she tried to write, shoot, direct, and edit in an effort to not relinquish creative control. "No one is impressed that you did everything when the work suffers." The learning curve for collaboration came when forming the writer's room for Insecure. The approach was to select people with different experiences and perspectives to make the room fresh and interesting. Through production for Insecure, Issa learned the importance of owning a particular point of view and not being lazy about the details. "My particular approach to collaboration prioritizes listening over talking. I've learned to be selective about when I speak, focusing on understanding why others feel strongly about their opinions instead of dominating the conversations. I want my input to be valuable and impactful when I do contribute." A brilliant outlook on selective communication. In March of 2022 Issa got the call for Barbie, in which she almost quit after accepting because she had to dance. Choreography has always been her biggest challenge. She embraced the challenge courageously and helped another creative see their vision result in a beautiful motion picture.

[Megan Collins · Rating 3 out of 5]

From a broad perspective I found this essay more relatable. It shows how self-awareness is more than identifying what bothers you—but learning why and then doing something in response. It’s also nice to see how even in creative fields people benefit from being intentional with their efforts and collaborations. Still the specific examples from Issa Rae’s career don’t widely apply to most people (without agents, shooting deadlines, and costumers). Further the repetitions moments are clearly snippets rather than a full story. Merited bullet points without productive advice, most engaging for fans. (2.5 stars)
* * * * * * * * * * * * * *
Despite the horrors learned from high school group projects, Issa Rae illustrates how working alone is inefficient. It’s hard to find a balance between maintaining creative authorship and growing from valid criticism. However, finding the right allies enhances your vision.

[January · Rating 4 out of 5]

Playing Well with Others by Issa Rae (2025)
I Should Be Smarter By Now #2
22-page Kindle Ebook story pages 5-21

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

Featuring: Amazon Originals, Television Shows, Collaborating, Writing, Acting, and Cultural Sensitivity, Directors, Barbie Movie

Rating as a movie: PG-15 for adult themes

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

My rating: ⭐️⭐️⭐️⭐️🫂

My thoughts: This certainly could have been one book but I'm sticking with it. I found these stories more informative than the first book, but the you can do it too is an afterthought.

Recommend to others: Sure.

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

[Kailee · Rating 4 out of 5]

"I fear collaboration would dilute my vision"

Wow, I loved this short essay by Issa Rae, read by the author herself! Her explanations of being particular were really relatable, especially the part about high school projects. I hated those for the same reasons!

Issa shows how you can have amazing experiences when you step outside of your comfort zone, highlighting this with a heartwarming story about her time on the Barbie set. Quite a moving story for something so short, I actually started to tear up a bit! (to be fair, I'll cry at anything)

Thanks to Brilliance Publishing for letting me check this out! My only complaint is that it is an Amazon Original and therefore may not be accessible to those that are trying to avoid Amazon.

[Donttouchmypoodle✨ · Rating 4 out of 5]

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.

[Lex · Rating 4 out of 5]

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!

[Rae Quigley · Rating 4 out of 5]

4.25 stars.

Issa has a great written voice, and I really related to the thought process that collaborating with someone else would ‘ruin the vision’ and that it’s better to sacrifice yourself to make sure it’s done exactly how you want it than to risk bringing someone else in.

Thank you NetGalley, Brilliance Publishing and Amazon Original Stories for sending this audiobook for review consideration. All opinions are my own.

[bookishreads · Rating 3 out of 5]

.

Playing Well With Others is witty and relatable, with Issa Rae’s trademark humor shining through. She gives an honest take on navigating relationships, identity, and collaboration, which makes parts of the book engaging and inspiring.
That said, some sections felt a bit uneven and dragged compared to her sharper moments. While I appreciated her candidness, I found myself wishing for deeper exploration in certain areas. Overall, it’s a good read with meaningful insights.

[TL Thomas · Rating 3 out of 5]

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.

[Rachel · Rating 4 out of 5]

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]

[Bre · Rating 5 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!

[Tanesha Abernathy · Rating 5 out of 5]

I like these little snippets of Issa’s experience getting started in the business and how to work with others. It’s good to know that even if you have control issues when you know it and can figure out how to manage it, in order to work well with others…the projects come out that much better.

I also enjoyed how she allowed others input and maintained her own creativity and authenticity.

[Bruce Dinsman · Rating 4 out of 5]

Now that I have read the Amazon description... This is from a series of video essays by the author under the overall title of "I Should Be Smarter by Now". Here she describes part of her creative journey where she discovered that working with others wasn't an abrogation of her talent as a star; it contributed to her process as well as her stardom.