When conversations about Issa Rae come up, her impressive list of accomplishments is usually front and center—and rightfully so. From her breakout YouTube series Awkward Black Girl to five seasons of the hit HBO series Insecure, Issa has built a signature voice in television, film, culture, and even beauty as co-founder of Sienna Naturals. She’s launched platforms like HOORAE to amplify underrepresented creators, opened gathering spaces in L.A. for Black creatives, and added her own twist to the on-screen canon of Black life in Los Angeles.
But in her new book, I Should Be Smarter By Now, Issa offers something more personal: a collection of six essays that feel like a deep exhale. They’re intimate, self-deprecating, and deeply relatable. In other words, they’re written for anyone who’s in the process of building something, questioning everything, or growing into the next version of themselves.
The essay collection I Should Be Smarter By Now is available now at amazon.com/IssaRae. Published through Amazon Original Stories, the collection is free to read or listen to with Prime and Kindle Unlimited. The essays trace her path from awkward adolescence to adulting in her 30s and 40s, with all the contradictions, clarity, and chaos that come with it.
That honest, messy middle—where ambition meets uncertainty and growth doesn’t always look graceful—has been essential in making Issa’s work so resonant and enduring. Whether she’s on-screen, behind the camera, or writing from the heart, she’s creating space for Black women to be multidimensional, evolving, and unapologetically human.
We caught up with Issa to talk about the new book, her beauty rituals, and the hairstyles that help her tap into boss mode.
ESSENCE: How did you land on the title I Should Be Smarter by Now?
Issa Rae: For me, it came from a place of feeling like, I should know better by now, now that I’ve had all of these experiences. I wanted to lend insight into some of my mistakes along the way because I get asked a lot about my journey, especially by aspiring dreamers, entrepreneurs, and creatives, and I wanted to make it clear: this is an approachable, self-deprecating guide to pursuing a dream.
A theme I’ve appreciated in your work is that, even when a character is “grown,” they don’t have it all figured out. In your 20s and 30s, and even this current chapter, did you feel like you had another coming-of-age? And how did writing these essays help you process that?
Absolutely. Very recently, I’ve felt like I’ve entered a new coming-of-age and I’m just now getting to the other side of it. I wanted to write this book because I’m a completely different person than I was when I wrote The Misadventures of Awkward Black Girl in my early twenties.
People still read that book, and it really is a time capsule, I even mention that in this new collection. Part of me wanted to update it, to show where I am now. I have a much clearer understanding of who I am—personally, in relationships, friendships, and even in business. I’m way more confident, albeit still awkward in certain circumstances. I just know myself better. But I also know I’m still growing, and I’m excited to keep challenging myself in ways I probably wouldn’t have before.
During this journey, have you added any new tools to your toolbox that you’re proud of?
One of the biggest tools I’ve added to my toolbox is the ability to be more honest and transparent as a leader. I’m just far less concerned about hurting people’s feelings or disappointing them. A lot of that comes from shedding the people-pleasing side of me.
You waste a lot less time—both for others and for yourself—when you’re just direct. I’ve realized that being upfront saves time for everyone, and most people respect and even appreciate that kind of clarity.
It’s been a delicate dance, one I’ve learned and am still honing. Even when you have to deliver a hard message or a hard truth to someone, there’s a way to do it gently. I’m still navigating the “gently” part, but the truth is there.
I don’t think I’d heard the term “workation” before reading your Art of Strategic Procrastination essay. In it, you talk about diving into creative work at oceanfronts. Since water seems to help you reset and recharge, does that carry over into other aspects of your self-care?
Definitely and I never really thought about it that way. I sleep to ocean sounds or rain almost every night. I’ve also gotten really into baths over the last five years. They’re incredibly relaxing, and now that I have a great bathtub, I love to sit in hot tubs, all those things.
I just feel at ease around water and I love to swim. When I bought a house it was essential to have a pool. I wanted to be able to swim whenever I want to and do laps and just rest in the water. That’s definitely my happy place.
In your essay “The Business of Being Me,” you write about how briefcases always signaled “serious business” to you growing up. Is there a hairstyle or style choice that gives you that same energy — like, when you rock it, you know you mean business?
Anytime I’m wearing a high bun, I’m showing up for work. I’m showing up for business. I love high ponytails and high buns. There’s something about the tautness that just signals, Oh yeah, I’m in work mode. I don’t have time for hair in my face. Let’s get to work.
On the jewelry side, I actually love wearing rings because I speak with my hands a lot (Laughs). There’s a particular selection I like to wear, and once I’ve got them on, it’s like this is my uniform for the day.
I feel that! Especially for writers, when you’re typing or writing by hand, having rings and a fresh manicure is such a vibe. It can be such a mood booster.
Can I just say, I was just in Lisbon and couldn’t get a manicure before I left. I told myself, Oh, I’ll just get one when I’m there. But I never got the chance. It’s a specific manicure, hard gel, all these things, and I was like, I don’t know where I’m gonna go for this… So I had the most busted hands the entire trip. I was so self-conscious.
Even when I got to New York, I had to send a picture of my hands to my friends like, Y’all… And they were like, Girrrrl. Go now. It had been a minute.
I loved seeing the different hairstyles on the covers of each essay. It felt like an extension of what we’ve seen from you on red carpets and in the Insecure universe. Why was it important to showcase that versatility visually?
Thank you for giving me an opportunity to highlight the artist, the illustrator Alexis Franklin. It was really cool to get what felt like a lookbook. She drew me, my hairstyles, and outfit selections based on the themes of each essay. It was almost like getting styled without having to sit in a chair or work with a stylist. She actually spoke to my stylist to get a sense of what I might wear in these scenarios, and then based the looks on different outfits and poses I’ve done in the past. I think about how Awkward Black Girl started with me shaving my head, and how the hair journey since then has been so integrated into my personal growth.
You’ve also co-founded Sienna Naturals, which really centers healthy hair and scalp care. Is there anything on the horizon or that folks new to the brand should have on their radar?
We finally have a gelée that we’ve been testing for some time that just dropped, the Dream Curl Gelée. If you have curly hair or textured hair, it’s amazing and our first styling product. The hold is great for defining curls and preserving a style without the crunch. It gives you solid hold while hydrating your strands, whether you’re doing a wash and go, braid-out, or wearing your natural coils.
What’s a simple pleasure you’ve been enjoying lately?
Running. That’s my happy place. No matter where I go, I’ve been packing running clothes. It’s been a great way to tour new places too. It helps me get out of my head, and I’m usually listening to music while I run. Even today, I finally got to listen to the new Blood Orange album. I’ll curate playlists for myself to run to—that’s generally my new music time.
This interview has been lightly edited for clarity and brevity.