I See You Seeing Me: I Should Be Smarter By Now

I Should Be Smarter By Now #4

by Issa Rae

A witty exploration of what it means to truly see yourself in a world that’s always watching by award-winning Issa Rae, costar of Barbie and producer of One of Them Days.

Remember a mortifying moment that made you self-aware? Honestly, Issa Rae remembers a few. In this illuminating essay, Issa follows her shoulda/coulda/woulda journey from awkward schoolgirl to a Hollywood life under the spotlight. Along the way she offers unfiltered insights into unwittingly courting controversy, curating a cautious but always authentic identity, and navigating the gap between private truth and public perception.

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: Short Stories, Audiobook, Nonfiction, Essays, Ebooks

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]

Secondhand embarrassment is my life. You don't know your race until someone else points it out to you.

Online dating is horrifying. Black women and Asian men have it the worst. These stats are horrifying, but true. I get why Issa used to live tweet her feelings. I did the same. It was embarrassing. I had to delete my account. As a public figure, she doesn't get this grace.

🎧 Thank you to NetGalley and Amazon Original Stories

[Sihle 🪻🌸🌷🌼🌝 · Rating 5 out of 5]

This book reminded me so much of Blood Orange’s Negro Swan album. That record speaks on how unrelenting and exhausting it can feel to be different, and why finding a community where you can be vulnerable and unapologetically yourself matters so much. Like the album, the book captures that tension between isolation and belonging. Being different makes it hard to navigate relationships, or even love yourself at times, but once you start giving yourself grace, it’s incredibly liberating. It’s a reminder that you need to show up as yourself; proudly, fully but also that not everyone deserves that kind of access to your most authentic self.

And just as a side note, I absolutely hate cancel culture. Sure, it’s done some good, but it has also given people who contribute nothing of real value this weird god complex. It’s wild how quickly people jump to conclusions without ever pausing to rationalise or consider nuance.

[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.

[January · Rating 5 out of 5]

I See You Seeing Me by Issa Rae (2025)
I Should Be Smarter By Now #4
19-page Kindle Ebook story pages 5-18

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

Featuring: Self-Awareness, Insecurities, Embarrassment, Foot In Mouth, African-Americans, Making Friends, Public Opinion, Fame-Related Anxiety, Social Media

Rating as a movie: PG-15

Songs for the soundtrack: TLC, Tupac Shakur, "Nice For What" by Drake

Books and Authors mentioned: Mean Girls by Tina Fey [based on] Queen Bees and Wannabes by Rosalind Wiseman, Act Like a Lady, Think Like a Man: What Men Really Think About Love, Relationships, Intimacy, and Commitment by Steve Harvey

My rating: 🌟🌟🌟🌟🌟🎤💬

My thoughts: This was very good.

Recommend to others: Yes. This is the best one so far.

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: If you’ve never experienced secondhand embarrassment, relatable empathy, or irritated bewilderment while in the company of someone who is not self-aware, it’s possible that you too may lack self-awareness. In Hollywood, where the stage for scrutiny is infinitely wider and the consequences more lasting, a self-awareness deficiency becomes glaringly obvious—yet it’s surprisingly common, even among those whose careers depend on understanding human behavior. An underrated quality, the awareness of self doesn’t mean the unawareness of others. In fact, empathy and self-awareness go hand in hand. Many women are innately self-aware, constantly attuned to the reductiveness of the male gaze and often concerned about the judgment of the female gaze. To further generalize, Black people in particular have to be self-aware. In response, some make themselves more palatable to combat prejudices and others resentfully peacock their feathers: “I know what I am and I know what you think I am and I don’t give a fuck. Enjoy the show.” Today, I fall somewhere in the middle, and I’m proud to say that I inch closer to the latter the older I get and the more I work.

[Monique B. · Rating 5 out of 5]

This short read is probably my favorite so far. I've never felt so seen 😂. I loved hearing more about Issa's childhood and storylines about her school years (which made me love her Misadventures of an Awkward Black Girl book). I laughed out loud and couldn't help but think "me too".

The main focus is self-awareness and being yourself. How many times have we conformed to what others are doing or what's likeable to end up not being our genuine selves?

I loved Issa's take on this!

[Arianne · Rating 5 out of 5]

“Self awareness can be insecurities cousin” smacked me in the face. Along with that confidence, self awareness, and insecurities can all coexist at the same time. This short 25 audible minutes chapter packed in so many life lessons.

[Alaina]

another banger from ms. issa! i feel like these books are little notes to speak life into ppl idk 😭

[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.

[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.

[Rae Quigley · Rating 3 out of 5]

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 particular story didn’t really stand out to me. I don’t know that I’ll remember it much in a few months. But I enjoyed listening to it in the moment.

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.

[Greyson · Rating 5 out of 5]

5⭐️ I see you seeing me was funny and gave me a clear message that I can relate too. This was beautiful.

[Ashley Jones · Rating 4 out of 5]

Elementary school began Issa’s journey to self awareness, where she was only one of two black girls in the class. They had just moved back to the U.S. from Senegal due to her father losing significant money trying to build a hospital in Dakar. Issa and her family moved to Potomac Maryland and her dad went to LA to build a family clinic. Kayla from Kenya was the only other black girl in Issa’s first grade class and Issa wanted to befriend her. Kayla was African like her dad but Issa’s over-eagerness was off-putting to Kayla and they didn’t connect. “It was my first real lesson in reading social cues and understanding that being yourself doesn’t mean you won’t make friends; it just means you’ll make the friends who are right for you.” Middle school was when the necessary period of life and social development took place where Issa discovered that people could just not like you for no reason other than you being yourself. In sixth grade Issa moved back to LA. Issa became more self aware about how the other kids viewed her and she learned to observe social dynamics before inserting herself into them. ‘Years later, as I developed characters for my stories, I would draw from these formative experiences, the complexities of identity, the need for belonging, the performance of self in public spaces.” Issa wisely states, ‘-that our perceptions of others are often reflections of our own insecurities, that social acceptance is both desired and dangerous, and that true self awareness comes from understanding the difference between who you are and who others think you are.” Once Issa began the pilot for Insecure it dawned on her she could be a public figure soon and she deleted twenty thousand tweets that spanned over seven years, so nothing could be found online that would taint her image. Issa’s first Twitter dragging occurred while Issa was on a social media break during the shooting of the third season of Insecure but it was an excerpt from her first book that was circulating that had people outraged. Issa handled her first controversy well and it died down after a week or two but it ultimately made her continue to limit how much she shared about herself and her opinions.

[Shoni Renee · Rating 4 out of 5]

Issa Rae’s I See You Seeing Me is a witty and reflective piece that dives into the tension between how we see ourselves and how others perceive us. Her voice is sharp, funny, and refreshingly honest, making this essay both entertaining and thought-provoking.
One line that really resonated with me, “Self-awareness can be insecurity’s cousin,” perfectly captures the emotional complexity Rae explores. She shows how confidence, insecurity, and self-awareness can all exist at once, and does so with humor and grace.
Her take on social media is also a standout: it matters to many, but it doesn’t define us. That reminder felt timely and grounding.
Overall, this essay is a smart, empathetic look at identity and perception, told through Rae’s personal lens, a great read for anyone who enjoys introspection with a side of humor.

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

[Ivoree Malcom · Rating 4 out of 5]

In I See You Seeing Me, Issa Rae explores something we don’t talk about enough: the power of connection & emotional intelligence. She reminds us that who we naturally vibe with isn’t something we need to explain or apologize for. Sometimes, it just clicks—and sometimes, it absolutely doesn’t. Either way, that’s okay.

Issa makes it clear that forcing relationships—whether personal, professional, or somewhere in between—is a waste of precious energy. If there’s friction or a mismatch, it’s not your job to mold yourself into something you’re not just to make it work. Let it go. Because at the end of the day, what’s meant for you will find you. Period.

This section is a gentle but empowering reminder to honor your intuition, trust your emotional read on situations, & not chase connections that aren’t meant to fit. Issa does a beautiful job of showing us that choosing peace over people-pleasing is not just smart—it’s necessary.

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

#ThankGodForARCs

[Megan Collins · Rating 3 out of 5]

In the contemporary context of audiences that grew up with social media, live tweeting, cancel culture, and openness regarding generalized anxiety—I think this section is a bit more relatable. Self-awareness is not just how you see yourself but too much focus on audience perception is unhealthy. You shouldn’t have to apologize just for being yourself and can’t force relationships, but you also need to question your behaviors. It’s not life altering advice, but it gives sympathetic vibes to how personality is now interwoven with the professional world.
* * * * * * * * * * * * * *
Issa Rae gives a few examples of embarrassing moments of her life and provides context to how those things helped her grow. Whether it was a lack of body kinesis or the refusal to delete an old social media post, these moments made it easier to step outside of herself and view how some people see her.

[Ruth · Rating 4 out of 5]

When I was in 8th grade, there was a rumor going around that I was a prude. A rumor started in large part by the way I dressed (t-shirt and jeans?). It was 1983, so being a prude was... bad?
The summer btw 8th grade and my freshman year of high school, I started finding my own style of dressing. Somewhere btw mod and punk (or as punk as one could be in the 80s).

My freshman year, due to how I dressed, there was a new rumor that I was easy. Um... these excessively baggy-ass clothes make me... easy? oookay.

Basically, at 14, I learned that people are going to talk about you no matter what, so... fuck 'em, right? If they aren't interested in getting to know me and finding out for themselves, them fuck 'em for real.

This essay of Ms. Rae's validates my feelings on this matter. She's much more eloquent about it.

[Reader · Rating 4 out of 5]

thoroughly enjoyed I See You Seeing Me by Issa Rae. As a longtime fan, I loved gaining a deeper look into the inner workings of her creativity and brilliance. The book beautifully highlights the lessons she learned while navigating self-discovery, self-awareness, and insecurities. It also touches on the powerful ways public narratives can shape how your life and situations are perceived.

What resonated most with me is the reminder that while you can influence how people view you, the real power comes from embracing your authentic self. At the end of the day, the best thing you can be in every situation is be unapologetically you.

[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.

Now this one was by far my absolute favorite out of the bunch. Issa was self taught that people will always have a set narrative of how they see you.

And a main important lesson in today's society that you shouldn't let online drama influence your life in reality. Both very important lessons that everyone should learn and keep in mind with every day life.

Issa as always did amazing with the narration with this one as well. Highly recommend this one most of all if you have no intentions on reading all the books.... READ THIS ONE!

[Rachel · Rating 3 out of 5]

This book is part of a 5-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!
I gave this book 3 stars because I learned the least from this particular section. Other sections were more insightful for me personally.


[Thanks to NetGalley for the Advanced Reader Copy]

[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!

[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.

[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 am enjoying this series…I’ve been reading between the other books I have on my TBR and listed as reading. It’s a good pallet cleanser and a good way to get some good non-fiction reading in, when needed.

Again, these are personal experiences of Issa Rae but they are very much relatable. She’s really not an out loud person so getting glimpses of her personal life and what she’s thinking when completing her tasks/goals has been enlightening.

Well worth reading!

[Bruce Dinsman · Rating 4 out of 5]

Thanks!

Thanks for the reminder that social media is important to a lot of people for a lot of reasons, but it isn’t the definitive factor in my life but I get where she is coming from. Another great, short essay perfect for running up my book count. Is this also possibly a podcast thing? Once again sorry but I did another one-star ding for language.

[Nikki · Rating 5 out of 5]

Self aware?

This was so real and relatable. Social media can make you question your every choice but your reality is just that. Social media is a small part of a very large picture. Issa explains this so well and makes it seem so easy to do better. Great quick read and reality check.

[Vintageprincess Ward · Rating 3 out of 5]

this one was eye-opening

I can see where people take everything to be real on social media and I kind of felt like he said as well when you make a comment or something people don’t really know what’s true and fast so they run with it and those who disagree feel like you shouldn’t have that type of opinion and then they have an opinion and it’s all of a sudden you against them.

[Cel · Rating 4 out of 5]

Inspiring

As a dedicated follower of Issa Rae's work, I found her authenticity to be a defining characteristic of her projects, including "Insecure." These concise essays were particularly well-received, and their release was perfectly timed for the Labor Day weekend.

[Michelle Boyer · Rating 5 out of 5]

PopSugar 2025 reading challenge #50

Just going to drop this here...

"Self awareness, while a trait that makes some of the best friends, lovers, leaders, and storytellers, is also a cousin of insecurity" (17).

[Jae Philon · Rating 4 out of 5]

We see you Issa

I love these Issa shorts, her perspectives as a writer and life lessons. Issa has this chilled comedic energy to her that spills into her pages. Shes witty and we can only appreciate experiencing these moments she retells.