The Art of Strategic Procrastination

I Should Be Smarter By Now #5

by Issa Rae

With her trademark humor and unflinching honesty, Issa Rae delivers an insightful essay about productivity, procrastination, and work-rest balance in Hollywood’s high-stakes hustle culture.

From the imagination stage to actually making the magic happen, writer-producer-actress Issa Rae is a multitasking phenomenon. She’s also an inveterate procrastinator. But even that’s part of her creative strategy. Blending personal anecdotes with practical insights, Issa explores the challenges of having to constantly deliver, the importance of “workations,” and the value of embracing a unique creative rhythm in an increasingly demanding world.

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, African American

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 5 out of 5]

As Earth signs, we finally disagree. I hate Mondays. Maybe I hate most days. I'm fine. Everything is fine.

Issa worked at CAAM? I love CAAM. If you're local, I love the monthly free yoga. Also gives me an excuse to roam USC. And BMO Stadium is in this area, if you're a LAFC fan. If you're not, you should be. I'm converting others right now.

I love how she talks about how Capricorn she is. I am very much a Taurus. Life is hard.

I am also a carry on queen! I hate checking a bag. Absolutely not.

I also wasn't a tequila fan until late adulthood. I love a spicy marg. God, I'm basic.

🎧 Thank you to NetGalley and Amazon Original Stories

[Sihle 🪻🌸🌷🌼🌝 · Rating 4 out of 5]

This perfectly captures the tug-of-war between loving work and hating the act of starting. I liked how she framed Mondays not just as another day but as a personal reset button, something about that felt really motivating instead of cliché. The honesty about procrastination, multitasking, and even the idea of a “workation” made it relatable, especially in a world that glorifies hustle culture. What stood out most was the balance: admitting that breaks, routines, and even sleep are just as important to success as the actual grind. It’s refreshing to see productivity talked about with vulnerability rather than perfectionism.

[Monique B. · Rating 4 out of 5]

An interesting take on procrastination. As a fellow procrastinator, it's always seen as a "bad" thing. Issa pinpoints on how this can be done strategically and can be more fulfilling than not. Who said the more time you spend on something, the better it is?!

Ahhh to be able to take a work vacation and meet all your goals/work expectations. I'm all for it. I liked seeing how she manages everything in her workload.

[Arianne · Rating 5 out of 5]

Overall message: destigmatizing procrastination, utilizing curiosity and self awareness to figure out why you’re procrastinating, and finding systems that work for you. All the self help books in the world can’t solve your problems because that author doesn’t know you or the why’s behind your behaviors.

[Rae Quigley · Rating 2 out of 5]

Nah. Issa lost me with this one. Proudly stating that you use Chat GPT… AS A CREATIVE?! Gross.

This whole novella is humble bragging about how much money she spends, which is normally whatever. Get your bag! But it’s just… idk read the room lol. Talking about strategically procrastinating for creativity, which could have been realistic especially for those of us that are neurodivergent, and then explaining all the ways you’re able to spend money to go on retreats or be in these lovely amazing places AND using AI to plan it all? In this economy and actual world climate? No thanks.

Issa has a great written voice, and listening to her feels like being on FaceTime with a friend. The entire collection so far has been enjoyable. But I won’t continue to support someone, especially a professional creative, that admits to using AI. If you’re using AI to plan vacations, it makes me wonder what else you’re using it for. Are you using it to write? To edit? Do you realize that AI is trained off the stolen work of artists and writers? Hard pass.

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

[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.

[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.

[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.

[Greyson · Rating 4 out of 5]

3.75⭐️ This lines up a series of strategies Issa uses to time manage. Everything from accepting certain days as resets and not spending time being idle even when on the phone.

[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.

This one by far is my second favorite out of the bunch. In this one she was talking about how she was juggling too many projects at once and how her work was clearly showing that and she wasn't making any types of improvements to her work.

I loved how she figured out her flaws in this one and made a strategic plan of procrastination that worked perfectly for her.

There was a little more emotion shown in this one which is why its my second favorite. She did an amazing job narrating this book as well. Highly recommend!

[Ashleigh Burden · Rating 4 out of 5]

Relatable! I love Issa’s story telling and applied life lessons in her career

[January · Rating 4 out of 5]

The Art of Strategic Procrastination by Issa Rae (2025)
I Should Be Smarter By Now #5
21-page Kindle Ebook story pages 5-20

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

Featuring: Productivity, Motivation, Vacation

Rating as a movie: PG-13

Songs for the soundtrack: “Party All the Time” by Eddie Murphy, Tamyra Gray, Kelly Clarkson

Books and Authors mentioned: A Song of Ice and Fire by George R.R. Martin

My rating: ⭐️⭐️⭐️⭐️🏖

My thoughts: This was very insightful and relatable.

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

Memorable Quotes: But alas, the act of beginning is the most formidable challenge. Getting to the point where I put my phone down—sometimes I’ll actually try to hide it from myself—hunker down in front of a computer screen, and type away is an entire process that has taken years to fully grasp. I finally realized that I need to waste time before I can make the best use of it. Let me explain. In my early days, managing my procrastination was simpler. I didn’t have anyone to answer to, and I was the only one dependent on my own success. I couldn’t afford to run away from my writing duties, so instead, I would “escape” by taking four steps from my apartment bedroom to my living room, and typing “Game of Thrones rip” into my laptop browser. I’d set up my computer on the coffee table in front of my red Ikea Klippan love seat, and immerse myself in that world—or in other movies or TV episodes that might inspire me to create something great—for hours at a time until I felt ready to get to work. Now, my ideal existence is a balance of professional achievement and personal fulfillment—a life rich with meaningful relationships, impulsive fun, and luxurious relaxation. Yet the reality of my career means constant demands: perpetual deadlines, endless correspondence, persistent obligations, and the relentless pressure of never-ending tasks to complete. There is always something to do, someone to answer to, someone who needs something, somewhere to be, and something to finish as soon as possible. To maintain my sanity, I try to create pockets of calm within my day-to-day activities and workflow. Sometimes this manifests as listening to one of my mood-curated playlists or turning up with my friends on a yacht or bingeing twelve episodes of a reality dating show. Most often, though, I find myself drawn to peaceful waterfront locations.

In school, I would wait until the last minute to study or finish assignments, cramming for an exam or staying up all night to write an essay on a book I took too long to start reading. But I would still manage to get an A or a high score, which fostered a belief that I could always “get away with it” or manage somehow. This pattern of procrastination followed by intense bursts of productivity seemed sustainable until I turned in a final assignment late for an AP literature class. My teacher wouldn’t accept the work, and it dropped my grade in the class, a class I actually really enjoyed, to a C.

[Ashley Jones · Rating 4 out of 5]

Multitasking and procrastination are two things that could keep Issa from making a passionate project great. Meetingless Monday’s were derived by Issa to ease into the week by planning and prioritizing. January first is a new beginning every year for resolutions and a chance to set new goals. An opportunity to take plans from the impossible to the possible in the new year and to hold yourself accountable by checking in quarterly to see how far on track you are or to re-motivate. Now with the relentless pressure of never ending tasks to complete, to maintain sanity, try to create pockets of calm within day to day activities and workflow. “Any way you put it, procrastination is a beast, no matter what your profession or who you are. There’s no use in beating yourself up over it. All you end up feeling is guilt, which can cause you to spiral and do even less work, and no one needs that kind of stress. This is why I have completely embraced procrastination as an essential part of my process.” After turning in drafts and drafts of underwhelming edits to well respected producers, Issa decided that she needed to change her writing process as it related to work and time. Multitasking can be an enemy to productivity. “The weight of unrealized potential, the burden of structuring my thoughts, the inevitable encroaching deadline, the anticipation of too-high (or low) expectations - these all lead to a cycle of avoidance that only puts more pressure on me.” Issa says, “What looks like procrastination is often just my brain needing time to process stuff.” Also relatable, “our periods of apparent procrastination might actually be essential incubation time - the brain working behind the scenes before the magic happens.” Thank you queen for a positive outlook on the idea of procrastination.

[Kate Wallace · Rating 4 out of 5]

I've really enjoyed this audiobook series I received access to through NetGalley.
Issa Rae's voice (literally and figuratively) is both soothing and inspiring.
I liked this "book" of the series as an ADHDer as I'm no stranger to procrastination.
It's reassuring and insightful to see how someone successful struggles with some of the same mental hurdles (she never says she has ADHD to be clear) about weighing your worth against productivity but having a hard time getting started, always wanting to multi task and realizing that she works best solo in uninterrupted large chunks of time.
A key take reflection for me was how scheduling in intentional procrastination can be productive and part of the process as your brain churns in the background, and you get ready to buckle down. Some great nuggets for me to take away and work to apply in my own life (using meetingless Mondays to feel excited about the start week while still easing into it).
I will say though, in this book she primarily talks about her process of tackling work at this point in her life - which felt like focused largely on booking workcations to luxury locations so she can block off chunks of uninterrupted but enjoyable time to be productive. A dream process for most of us. The method makes sense at her level of fame and success, but is not too accessible to the average listener. There are tidbits to take away for sure, but I wish she had talked a bit more in detail how she learned her working style and applied these methods earlier in her career to get to where she is today.

[Ivoree Malcom · Rating 5 out of 5]

Issa Rae does it again—this time, with a hilarious, honest, & surprisingly insightful take on a habit we’ve all been shamed for: procrastination. In The Art of Strategic Procrastination, she flips the narrative, showing us that delaying tasks doesn’t always mean laziness—it can actually be a form of brilliance, if you know how to wield it.

I loved how she reframes procrastination as a tool, not a flaw. This book had me nodding all the way through because it felt seen. Throughout my K-12 years, I swear my best work came out of last-minute chaos. I even experimented once—did the assignment way ahead of schedule—& got a grade that was way lower than my usual procrastinated masterpieces. Issa just gets that energy!

What really stood out is her recognition that success isn't one-size-fits-all. We all have different creative rhythms & work styles, & figuring out our own process is where the magic happens. For some of us, pressure is the secret ingredient. Once you understand your flow, Issa says, you can lean into it without shame—& that’s when you become unstoppable.

The Art of Strategic Procrastination isn’t just relatable—it’s empowering. It gives permission to embrace what works for you, even if it looks different from what society tells you is “productive.” & baby, once you hone in on your unique path to success? The world better watch out.

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

#ThankGodForARCs

[Megan Collins · Rating 2 out of 5]

Once more I think experiences will vary here. In essence, Issa Rae found a positive way to interpret a “problem.” This acknowledgement prevents it from becoming a larger issue. You schedule your life for the person you are, and not the one you want to be. Maybe you need to lock out entertainment sources and apps which distract you or set your clocks ahead a few minutes. Her process helps her, but it isn’t necessarily actionable for others. While I love the reminder that you don’t have to be perfect, there was a bit of a ick factor (or hints of privilege) about how she just takes separate vacations for work and for play which many writers (and people) can’t dream of doing.
* * * * * * * * * * * * * *
Issa Rae discovered that although she loves working, starting projects is very difficult for her. After bumping up against things that didn’t work like outings with friends, spacing out meetings, and saying yes to multiple projects at once—she learned procrastination was part of her creative process. Now she plans for it with personal resets and expectations.

[Shoni Renee · Rating 4 out of 5]

Thanks to NetGalley and Brilliant Audio for the listen.

In this short, witty essay, Issa Rae explores how procrastination isn’t always the enemy. Sometimes, pausing on purpose gives your mind the space it needs to recharge, recalibrate, and come back stronger. She makes a compelling case for building in downtime intentionally not as avoidance, but as part of the creative and professional process.

One takeaway that stuck with me: make room for slow starts. Creating breathing room, like “meetingless Mondays,” can actually fuel more focused work later in the week. It’s a smart way to ease into productivity without burning out.

Much of this essay focuses on what her workflow looks like now think beautiful workcations, structured focus time, and premium locations that inspire her. It’s not exactly accessible for everyone, but the idea behind it is solid: protect your time, create conditions that help you thrive, and don’t feel guilty about needing rest to do your best work.

Quick, thoughtful, and funny.

[Neesh · Rating 5 out of 5]

Super insightful!

As a fellow Capricorn and perhaps because of my cultural background, I too have long associated my worth with productivity. Where I differ with Issa is that I don't struggle with procrastination-- in fact, I constantly work and work, usually until it ends in burnout. What I have noticed though, is that my best ideas and problem solving does happen during those forced breaks, so seeing her process really makes it all click for me. I have been working on relaxing more and purposely trying to take more breaks, and this was a good reminder that those breaks are just as productive!

[Donttouchmypoodle✨ · Rating 3 out of 5]

Side note: this was my last favorite of the bunch. I felt it could’ve been combined with “The Geography of Creativity”.

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.

[Elethia Gay · Rating 5 out of 5]

The Gentle Nudge That I Needed

I read this with a level of bias. I love Issa Rae from Insecure to the Hilltop. For a while, I have felt this magnetic pull and gentle guidance towards writing. As I considered reentering the zone, I would see caution tape reminding me of what I didn’t accomplish the last time. I remembered how my impatience quenched by instant gratification, distracted me from my inner guidance. That said, this short read and gentle nudge is the reminder that I needed.

[Rachel · Rating 4 out of 5]

This theme resonated with me, perhaps articulating what I already knew instinctively.

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]

[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!

[Tanesha Abernathy · Rating 5 out of 5]

Funny because I too procrastinate. I feel like I do my best work at the last minute when in all actuality I probably don’t. Realizing the same thing Issa learned in High School it’s best to take the time to gradually produce good work. I must say I do agree with her in terms of working with others in groups how one person usually ends up with all the work in order to get a good grade (that was me in school). Now, I wish I could summon that amount of energy to get my own stuff accomplished.

[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.

[Zakiya Daniel · Rating 5 out of 5]

#Relatable

5⭐️ - Straight To The Point, Self-Recognition Session

I love the way Issa Rae reframed procrastination—it’s only a problem if it gets out of hand. If we figure out a way to own our procrastination and harness it in a way that works best for us, we can enables ourselves to be productive in our OWN way. Of course, that process takes time, practice, and self-reflection, but it’s not impossible, which is reassurance enough for me. 😁

[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!

[Wondrously Bookish Cristina · Rating 3 out of 5]

While I appreciate the idea of fully embracing what ought be regarded a personality flaw as a specific strategy to be intentionally deployed in the hustle culture we live in today, I feel that this essay didn't provide me with enough actionable information.

Might still give another essay from this essay another change.

Thank you Netgalley for this ALC.

[Arathy · Rating 4 out of 5]

i genuinely do not like how this set of books is listed on goodreads.
this for me was the most relatable essay for me personally. she talks about people who are able to just work throughout- at breaks, between takes etc., but she needs lots of breaks/vacations to function. i want more people to talk about this anti-hustle culture, personal resets, slow work ideas.

[Vintageprincess Ward · Rating 4 out of 5]

procrastination

As a writer myself, I can understand what she’s talking about procrastination and getting into your zone and that’s exactly why I don’t have a book written yet cause my procrastination and getting into my zone keeps getting interrupted by the way of the world. However, 2026 would be my end. I’m gonna focus and get it done.

[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.