Issa Rae told us the secret to embracing your awkwardness (and some other brilliant things)

It’s been an awesome week for Issa Rae, queen of our awkward hearts and creator of the award-winning web series, The Misadventures of Awkward Black Girl. The writer, actress, director, producer, and all-around web series wizard has been working hard, and earlier this week, HBO announced a pilot order for Insecure, the show she co-created with Larry Wilmore; news that has only fueled our excitement that her much-anticipated book comes out today!

The Misadventures of Awkward Black Girl is a hilarious, super honest collection of essays that feels all too relatable—tackling everything from feeling feelings about body image and race to what it’s like having an immigrant parent (it’s a distinct experience, trust) to the nuanced greatness of growing up in the 90s (a/s/l?). It’s some pretty rad stuff, and if “J” is Issa Rae’s alter-ego in ABG, we are totally feeling her Peter Parker.

And because we are all just a little bit weird and forever working on embracing that weirdness, we chatted with Issa about how she’s turned her self-described “awkwardness” into so much awesomeness.

HG: Awkwardness is awesome, obviously—but when did you first start to own yours? Was there a particular turning point? Any tips for others trying to do the same and embrace a little self-love? 

IR: I don’t think I really started to own it until I knew what I was. When I diagnosed myself as “awkward and black” that fateful, lonely day in New York, it was almost useless, because I had already finished middle school, high school, and college. Had I known that about myself earlier, and embraced it sooner, I would’ve probably gone about things with more clarity. So, I guess that’s my advice to others—notice the signs and just accept it. Things are so much easier when you accept that you’re just socially uncomfortable in general.

HG: You touched on some pretty amazing ‘90s TV in your book. Who were some of the most important, formative, relatable characters for you growing up? (Books, TV, movies, etc!) 

IR: Oh man, Francine Pascal (yes, of “Sweet Valley High”) had this series of books called “Fearless,” and the lead character of that was so damn dope, and awkward in a fiercely, badass way. I devoured those books my freshman (and probably sophomore) year of high school; then they just stopped; which made me feel like more of a loser because that meant nobody else was really reading them. The TV side is less “embarrassing” because I grew up with so many great examples to aspire to—Fresh Prince and A Different World made me and so many other kids want to go to a diverse college. Family Matters—Laura was so damn relatable! I always say that Freddie from A Different World and Sinclaire from Living Single were the original awkward black girls on TV—even though they weren’t explicitly labeled as such. The movie that made me want to write and make movies was Gina Prince Bythewood’s Love & Basketball. Sanaa Lathan as Monica just really touched who I was at the time.

HG: That Junot Diaz quote you mentioned early on in your book hit us right in the feels. If not quite the “monster” within, what most inspires you to create? What is the main pull for you as an artist? 

IR: Isn’t that quote the best?! Someone else sent it to me within the first few episodes of me releasing “Awkward Black Girl.” I’m most inspired to create what I want to see, as selfish as that sounds. More recently, with a series I’m writing called, “The Legend of Human Black Guy,” that’s spurred by a desire to combat the “monstrous” image of black men. But generally, I draw inspiration from things that make me laugh and go from there.

HG: As a WOC, I could not be more excited to see nuanced, complex, and compelling women of color represented in media lately, particularly on TV—but it still feels like an uphill battle. Projects like Color Creative feel so important, and I was curious if you have any advice for young women, particularly women of color, who feel discouraged by the diversity problem. 

IR: Me, too. I’m so optimistic about what’s to come. My advice to young women who feel discouraged is to either create what you want to see or to seek out and support what you find on the Internet. I would never be on the path I am today had people not done the latter. The encouragement lies in knowing that you’re not the only one who feels the way you feel and so many people are working outside of the system to create some great stuff.

HG: Speaking of, we love, love your web series so very much. Are there any topics/situations you haven’t yet covered that you’d love to do an episode for? (Also, will there be more episodes anytime soon?!) 

IR: Thank you! There definitely are scenarios I want to explore, but I have more awkward living to do before I put out more episodes. There’s a whole new level of awkwardness in the entertainment industry that I want to explore, but I want to make it relatable.

HG: Any advice for aspiring web series creators? Side note, “webpreneur” is a word I did not know existed, but a thing you have so clearly mastered. Can you tell us more about the world of “wepreneurship”? Are there essential pointers everyone should follow? 

IR: Ha!I didn’t know that word existed either. I don’t think I like it. Who made that s–t up? Because it’s pretty wack. But for the sake of answering the question, I think everyone who creates online content inevitably becomes an entrepreneur. You’re doing so much more than making videos: you’re marketing, you’re servicing your audience by communicating with them, making sure you’re providing great customer service; you’re trying to keep your “brand” or “product” afloat in new and innovative ways; you’re trying to keep up with the various mediums that emerge. There’s just so much to think about. But through it all, it’s really important to not lose your creative vision. It’s so easy to get wrapped up in the business side and forget that you have to still create good stuff. That’s the most important thing. Nobody cares if you’re a great businessperson if you’re standing behind wack content. So there’s a balance to maintain.

HG: What’s the best advice you’ve ever received during a less-than-confident time? (For us awkward girls that haven’t quite gotten the hang of it yet.) 

IR: “It could always be worse.” Perspective is everything, and all I really have to do is think about how bad my situation could really be and I tend to wise up.

HG: Aside from the obvious, what are your must-read books for awkward girls everywhere? 

IR: “Bossypants,” by Tina Fey, “I Was Told There’d Be Cake,” by Sloane Crosley, “Is Everyone Hanging Out Without Me,” by Mindy Kaling, “Yes Please” by Amy Poehler, “Meaty,” by Samantha Irby.

HG: We have to ask: was working with Shonda Rhimes as incredible and life-changing and magical as we imagine it to be? (Major fangirls over here.) 

IR: Yes. Absolutely. I will always cherish that experience. Betsy Beers and Shonda are the absolute best, and I really wouldn’t mind if they ruled the world.

HG: What’s next for you? 

IR: I really want to produce a movie. My producing partner has been on my back about making that happen for a long time, and I’m working on it, but I need to finish.

The Misadventures of Awkward Black Girl comes out today, February 10, and Issa Rae kicks off her book tour tonight with a reading at The Last Bookstore in LA! If you can’t meet Issa on her tour, you can also join her on March 10th for a live web chat about the book. Go to for more information, and buy The Misadventures of Awkward Black Girl here!

(Image via.)

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