I Almost Know What I'm Doing

I Should Be Smarter By Now #6

by Issa Rae

A fearlessly authentic essay about the entertainment industry—the setbacks, high-stakes risks, and hard-won successes—by Issa Rae, named one of Time magazine’s most influential people in the world.

It’s a gamble to bet on yourself in Hollywood. But Issa Rae placed it. Charting her evolution from struggling writer to media mogul, she pulls back the curtain on her ever-evolving career in an always-changing industry and reveals that the best investment she made was her belief in herself. As she reflects on weathering storms and lessons learned, Issa moves forward with renewed purpose.

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

21 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]

While I was a little less interested in this one than some of the others, it was still interesting. I know a little about TV production, due to my middle school bestie, but (male) screenwriters have turned me off from writing rooms, and hearing about them.

🎧 Thank you to NetGalley and Amazon Original Stories

[Alaina]

issa is so refreshing. loved this quick listen about the inevitability of mistakes

[Sihle 🪻🌸🌷🌼🌝 · Rating 4 out of 5]

“I Almost Know What I’m Doing” succeeds as a thoughtful, nuanced finale. It wraps the themes of the preceding essays but doesn’t try to neatly tie them all with a bow. Because Issa is still “in process,” the essay’s power comes from that honest liminality. It leaves the reader encouraged, grounded, and aware that even success includes doubt. As an ending, it feels true, human, and fitting.

[January · Rating 4 out of 5]

I Almost Know What I'm Doing by Issa Rae (2025)
I Should Be Smarter By Now #6
20-page Kindle Ebook story pages 5-18

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

Featuring: Amazon Originals, Self-Actualization, Failure and Growth, Television Show Production

Rating as a movie: PG-15

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

My rating: ⭐️⭐️⭐️½📺🖥

My thoughts: I get why this was the last story, but it felt a bit hurried.

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

Memorable Quotes: Every major mistake I’ve made seems to come down to two things: my impulsiveness and my fucking mouth. Or, more euphemistically, to communication—whether I’m too blunt with an opinion or not properly articulating a need or not being enough of an open book. Speaking out loud and articulating my thoughts and feelings has always been a challenge for me—it’s part of the reason I love to write. I can take the time to gather my thoughts and self-edit. I can be vulnerable and transparent without having to watch the person I’m addressing react to my words.

[Shannon · Rating 4 out of 5]

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.

[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.

[Monique B. · Rating 4 out of 5]

Issa sums up that she has learned a lot over the years and is still learning. Honesty & communication are key! If you don't know or understand something, ask.

Through failures and wins, her tone through this short series is comical, yet honest. I enjoyed Issa sharing her mistakes & little things she's learned along the way. I admire that!

[Arianne · Rating 4 out of 5]

“Every major mistake I’ve made always seems to come down to two things: my impulsiveness and my fucking mouth” attacked

[Greyson · Rating 3 out of 5]

3⭐️ This outlined the highs and lows Issa went through in “making it” in the industry. This essay was inspirational in the way that she is saying eve when stuff looks bumpy and quitting feels best, keep on keeping on. I liked it but the central point was… regular.

[Jay DeMoir · Rating 4 out of 5]

Solid advice and insight

[Ashley Jones · Rating 4 out of 5]

Issa’s love for writing comes from her impulsiveness and the challenge of speaking out loud and articulating her thoughts. Through writing, she can take her time to gather thoughts, be vulnerable, and transparent without having to face a person’s reaction and she can self-edit. Her lack of communication was evident during ABG early on when the four people who worked for her wanted equity in the show, which Issa was unable to figure out and properly articulate her future plans for the show. Issa describes other instances where her mouth and big ideas get her into trouble like working on 3 pilots simultaneously without having funding secured or investors locked in that lead to her spending all her savings to fund projects that were in production already. She spent all the money she got from her first advance on her book deal. Issa talks about how her reps re-negotiated her contract for Insecure in the fourth season that resulted in life changing money. The industry then changed and production halted for nearly a year during the pandemic. The rising production costs and the writer and actor strike caused two of Issa’s shows to get cancelled. Through that devastating lose Issa built her own production company called HOORAE. “I’ve learned that investing in yourself isn’t just about money, though sometimes it costs everything you have. It’s about betting on your vision even when others can’t see it yet.”

[Ivoree Malcom · Rating 5 out of 5]

In I Almost Know What I'm Doing, Issa Rae serves up a perfect blend of humor, wisdom, & real talk. This title is a masterclass in using what you’ve got to get where you’re going—while knowing when it’s time to push forward or gracefully step back. It’s all about trusting yourself, even when life feels like a wild, unpredictable ride.

What I love most is how Issa reminds us that mistakes aren't something to run from—they’re something to champion. Owning your missteps instead of letting them define you is key to growth, & Issa lays that truth out with vulnerability, wit, & a wink.

She also digs into the importance of knowing your limits—not as a weakness, but as a form of self-protection. Because let’s be real: if you don’t set those boundaries, who will? That message hit home in the best way.

Ultimately, this title is a boost of encouragement for anyone who's ever felt like they’re figuring it out as they go (which is, let’s face it, all of us). Issa gives us permission to keep moving forward, even when we’re unsure, uncomfortable, or under pressure. Because sometimes, almost knowing what you’re doing is more than enough to make magic happen.

*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.

[Leese · Rating 5 out of 5]

Wow, wow, wow. I didn’t foresee receiving so much insightful guidance in just over 100 pages. I took note of a ton of quotes in this collection from Issa. Each essay provided great storytelling, key lessons and takeaways, and more insight into Issa’s life experiences. Honestly, everyone should read this collection but anyone who wants to get into the entertainment industry or pursue a creative profession should definitely read this. Understand the musings and mistakes Issa has made and help them influence your decision making. One of the key points that I’ll be taking with me is the importance of self-awareness and knowing yourself.

“My authenticity has become a source of confidence, because I’m standing firmly in who I am right now, and I’m excited about who I’m yet to be.”

So glad I read this, highly recommend!

[Rae Quigley · Rating 4 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.

I really enjoyed this essay, and felt Issa did an amazing job taking us through some of the highs and lows of starting her career in Hollywood. I think it’s a great lesson about what to avoid when starting out, especially when pushing your own projects, but also showcasing the resiliency needed to keep going despite the many ‘No’s you’ll receive.

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.

[Shoni Renee · Rating 4 out of 5]

Thank you to NetGalley and Brilliant Audio for the advanced listening copy of this short audio essay focused on self-reflection.

In this piece, Issa Rae opens up about the not so glamorous side of leading a project. She walks you through the doubt, the learning curve, and the moments when she had no choice but to figure things out on the fly.

What I appreciated most was her honesty around mistakes. Instead of running from them, she talks about embracing them how those moments shaped her growth and sharpened her instincts. Her take on setting boundaries also stood out. She reframes it as a form of self-preservation, not weakness. That hit home.

Issa reminds us that leadership doesn’t always look polished. Sometimes it looks like questioning yourself while still showing up. This essay is a quick, thoughtful listen that encourages you to keep pushing forward even when you’re unsure.

A great pick if you enjoy honest storytelling with a touch of humor and depth.

[Megan Collins · Rating 2 out of 5]

Issa Rae has an openness to her writing and narration. She keeps a positivity to her advice and contemplations. The bullet points of her journey through the entertainment industry don’t personally connect with me which might affect my ratings.
* * * * * * * * * * * * * *
Issa Rae wraps up her essay series with a little more reflection on mistakes, acceptance, and boundaries. Specifically, she looks at how impulsiveness and poor communication created issues in writer’s rooms and kept her focusing on the wrong things throughout her career. While she loves the time and distance writing gives her from the audience, she needs to speak her thoughts directly when dealing with other professionals to achieve her goals.

[Rori.c · Rating 4 out of 5]

Mistakes and the Cost of Growth

I Almost Forgot What I Was Doing by Issa Rae is a sharp, engaging short story that captures the investment and resilience it takes to reach your potential. Rae shows that daring means stumbling, sometimes publicly, but mistakes are not dead ends; they’re lessons that fuel progress.

The story highlights how setbacks, ownership of losses, and weathering the storms are essential to transformation. Rae doesn’t shy away from the truth: success is rarely seamless. It is messy, built on failures that strengthen your vision and sharpen the determination to achieve the dreams set before you.

[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!

[ERIS · Rating 5 out of 5]

I truly enjoyed these mini story collections. I previously read Awkward Black Girl and enjoyed learning about Issa and how she became who she is today. Having Issa narrate the audiobooks made it more exciting, animated, and authentic. I learned a lot from her shared experiences with making mistakes in life and business. As someone that is close to the end of her twenties, I feel motivated to embrace failures and use them as a way towards growth instead of letting it be a setback. I look forward to more of her stories.

[Misse Jones · Rating 5 out of 5]

nice closing to an overall great series!

This last installment drove it all home for me with an urgent message that no matter what happen to keep going. You'll have your share of successes and losses but they will culminate into learning experiences that will help grow you as an individual and as a leader in your respective industry. I'm proud of the work that she has done to date and I look forward to all that is to come. Issa has become a household name and I'm happy to see it!!

[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 5 out of 5]

This was my favourite out of the series, by far.

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]

[Ruth · Rating 4 out of 5]

This starts with Ms. Rae describing how she functions and acts. It was very much like listening to a mirror (not a thing, I know). So hearing how she dealt with that and still succeeded was very hopeful for me! hah!

It was fascinating learning how the industry works and her insights on it all. I listened to these out of order, as I've now listened to the first and last in the series. Looking forward to the rest of it!

[Lala · Rating 5 out of 5]

I LOVED this entire series!! Now I feel like reading her memoir, especially if she's doing the narration. It's something about that person telling their story, that works for me. Nobody can really get the language, emotions, and tone exactly how they had it in that moment of time. I mean coaching/feedback does exist but for me having them walk through their own life is preferable.

The title works perfectly as do the rest from this series. Just lovely.

[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!

[Bruce Dinsman · Rating 4 out of 5]

COVID DID IT AGAIN!

Now I know that isn’t completely true, but COVID did knock a lot of us on our butts. Mad respect for Issa and her transparency that lets us see the processes, warts and all. Mostly I respected her nod to dusting yourself off and getting back in it. Sorry again but a one star penalty for language.

[Joseph Fisher · Rating 5 out of 5]

This was the sixth story in a collection of short stories by Issa Rae. They’re all about her experience working and developing in the entertainment industry. I found them to be funny, insightful, and very entertaining. I found a lot of the themes to be something that you can use in your everyday life. Also, I could listen to her talk about anything honestly, a very enjoyable read.

[Tiffany · Rating 5 out of 5]

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.

[Tanesha Abernathy · Rating 5 out of 5]

This was a good motivational series. I enjoyed all the little gems given through her mistakes and triumphs. This was a great wrap up to let everyone know no matter your trait (impulsive or hesitant) you too can be successful.