Issa Rae On Friend Breakups, Emmys Regrets, & Expanding Her Empire

The Insecure creator and star talks to Elaine Welteroth about Emmys regrets, friend breakups, the moving goal post of success, and whether celebrities can persuade voters.

Issa Rae still identifies as an awkward Black girl. But in the almost 10 years since her breakout web series, The Misadventures of Awkward Black Girl, the actor, writer, and producer has ascended the world of film and television with ease and grace. The creator and star of the Emmy- and Golden Globe-nominated Insecure, 35, has a reputation for publicly highlighting the work of other Black creators while privately nurturing their careers, earning the title “the patron saint of Black millennial creatives." As quarantined viewers dug into Insecure season four this spring, Rae found time to send up the privileged earnestness of the #resistance in HBO’s Coastal Elites, a series of monologues written for the stage and adapted for the front-facing camera. For Bustle’s Rule Breakers issue, Rae hopped on a Zoom with Elaine Welteroth, the groundbreaking editor, Project Runway judge, and author of New York Times bestseller More Than Enough.

Elaine Welteroth: Yes, come through beat face. Where you coming from?

Issa Rae: Girl, I had shit to do today. You know how it is. It’s a back to normal week.

Elaine: Right. All of a sudden it’s go-time again, and yet the world is still crumbling. After that Kentucky grand jury declined to charge the officers who killed Breonna Taylor, it’s like, "Hold up, I’m not really ready for all this yet."

Issa: I had a work call this morning with my colleagues. The first thing, I was like, "Man, I hate how facts don’t exist anymore."

This is my whole thing right now: The facts of [the Breonna Taylor story] are clear. They’re already tragic enough. We don’t need to add extras to the narrative. Even hearing the Daily episode about Breonna Taylor, I was like, "That cop who was in the parking lot for sure need to go and be arrested for murder. He needs to be locked the fuck up because he was reckless and has no regard for Black life or people."

Then it was, "All right, can we transition into what this work shit is?" Because that’s the escape. I have to compartmentalize it to get shit done or else you’ll go crazy. I had to login to Twitter to do something, and then I saw the feed. I don’t even like logging in, because you get wrapped up in that.

Elaine: Most people I talk to in real life are on the same page as me. But yesterday, when I made this post about Breonna Taylor, I was shocked at some of these Trump supporters and conservatives with these conspiracy theories that were in my comments.

Issa: I was watching this stupid ass conservative guy and torturing myself last night. He was talking about how Breonna’s boyfriend was a criminal and she was involved with him and that’s why the police shot him. I was like, "OK. Her ex-boyfriend was a criminal. The one that she was with in the apartment fired a shot because he thought there was an intruder. Yes, they knocked. But people did not hear [them announce themselves]." We know these facts, but all that gets thrown out the window because of emotions. We don’t get anywhere, and nobody’s right.

Elaine: There’s a lot of misinformation on both sides. Listen, I went deep into the counter narrative just to understand, why do they think what they think? Also to challenge why I think what I think. Before I get into these fights with people on the internet, which is something I normally don’t even do, let me make sure I have my facts straight. What I realized is a lot of us don’t have our facts straight about this.

Issa: We don’t. We need to get our facts, too, because that shit matters. Because that’s how they discredit us. Whether she was shot in her bed or not, it still doesn’t change the fact that she did not deserve to die. She doesn’t need to be a perfect victim to deserve justice.

Elaine: Absolutely. I’m also like, "I have dated a drug dealer. I didn’t deserve to die for it and neither did she."

Issa: Exactly. So many people have dated fucking criminals. People have done shit. You don’t deserve to die. Cops do not need to kill you. Get the fuck out of here.

Elaine: Do you know any Trump supporters or undecided voters?

Issa: No.

Elaine: Neither do I. Even that’s scary. I wish I did, because then we could understand it a bit more and speak to it.

Issa: The separation is just, it’s so wide. But I wouldn’t have those people in my life, unfortunately. I don’t know that I could be forgiving of it.

Elaine: We may not know Trump supporters, but we know Black people who may not vote.

Issa: That I know plenty.

Elaine: I also feel there are narratives around voting that are not speaking to the moveable Black base. Right now, we’re all talking to ourselves. We’re talking to the liberal progressives who are already going to vote. You know what I mean?

Issa: That’s where I get discouraged. Nobody who is on the fence wants to hear from me. I’m not going to change their vote. The people that I reach will either already vote or won’t be impacted by me. I don’t know what I can say to change that because I now have crossed over into a different … whatever. I don’t even know how to categorize it, but I’m not considered [air quotes] "of the people," in a sense. People aren’t relating to me in the same way. It’s like, "OK, you might be cool and all, but you’re not going through what I’m going through. You don’t understand my struggle."

Many of the conversations I’m having with other public figures are about how we can empower the people on the ground who can reach people and who understand the plight a bit more.

Elaine: I think that the place to start is actually with our own family and our own friends, the people we know in real life, getting off of social media. Because I know there’s people in my family who, depending on how they feel that day on Nov. 3, may not vote.

Issa: Yes. I agree. But your family? Really?

Elaine: You know what? My mom’s side of the family is pretty apolitical, and I think for certain Black folks, that’s the case. Politics have always been misrepresented as a privileged people’s concern. They are focused on putting food on the table, you know what I mean? I also think there’s an insecurity in the lack of education about how the system works. Certain elders in my family weren’t afforded the luxury of an education past tenth grade. Voting is confusing for my ass and I went to college. I’m like, "Wait, what? When do you turn it in? How do you get your ballot?" Who’s going to help our grandparents get over that barrier from a confidence perspective, if not us?

Do you know people in your family who are on the fence or against voting?

Issa: A specific side of the family, certain members, but for the most part people seem mobilized. Yes, I have a couple of people where they’re like, "There’s no hope," or that’s the conspiracy theorist cousin and it is what it is. But also, even some family members who live in California, I’m like, it’s not going to really make a difference whether you do or not as much as it will for certain states, and they recognize that, too. So that’s not the fight that I want to have.

Elaine: It’s been a crazy, crazy ass year on all fronts. Aside from all of this, how are you feeling?

Issa: Beyond what we just talked about, I have been finding a routine for myself and my health and my sanity. I’ve been good about giving myself time and space to breathe. I have weekends for the most part and really get to say, "I’m not doing shit." I have a cutoff on certain days where I’m like, "I’m not going to do this past a certain time," and that feels good, to be able to do that.

Elaine: Quarantine has slowed a lot of folks down and given us a chance to reflect and refine what we’re chasing and why. Is there anything that you feel like you’re going to carry over into the new normal?

Issa: Definitely taking my time. Like, why am I working? Why am I killing myself? Yes, I can still be a hard worker but also have time for myself.

Elaine: And not feel guilty about it.

Issa: And not feel guilty about it, because it is like, who am I doing this for? I’m only doing this for myself. I don’t know what I’m competing against.

Elaine: You’ve done so much; your credits are so impressive. You are that bitch. If you stopped today, you would have respect on your name forever. So what is the motivating force for you at this point?

Issa: That I don’t feel that. Every single time you do something, there’s a moving goal post. I still feel like I have so much more to do and so much more to prove. To the point of competing, I guess, with myself or with some invisible being just ahead of me, I don’t feel any impact yet. And a lot of that comes with time. Yes, 2007 was 13 years ago, but [it] feels like it’s been two years. I’m like, "I need more time."

Elaine: Your work defined so much of 2020 for me. I started the year celebrating Season 4 with you guys at the fucking best party of Sundance, which was the Insecure party, which you basically slept through…

Issa: Shh. Shh. I was tired. I was so hot when I saw you guys’ stupid ass Insta stories, dancing on tables and shit. If we had stuck to our guns and stayed at that one party instead of party hopping… I have so many regrets. I have so many regrets.

Elaine: I’m not going to lie to you: That party, I don’t need a party again for the rest of 2020, maybe the decade. I’m done.

Issa: You are the rub-it-inner. You are that. You’re not the "Oh, girl, you didn’t miss anything."

Elaine: I’m sorry. I feel bad for you, but you missed it. But I do want to talk about this season, because you went the fuck off. Season 4 was hands down the best season of Insecure. Did you feel that when you were watching it? Or even when you were creating it?

Issa: In creating the season we felt like, "Oh, this feels good." We had taken a year off and even coming back to the writer’s room, we all felt refreshed. It felt like Season 1 again, and it was really fun. And the territory that we were going down, everybody had a story in the room about some sort of friendship breakup. We were mining from different people’s stories to put it into these characters.

But when it airs, you’re still nervous. I always think about what people expect from our show. … People always expect gender wars, and that’s not what this season is about. So of course certain people are going to be disappointed because it is about the female friendship. That’s what I was excited about, recentering them in this series.

Elaine: There was something really rich and complex about [that] exploration of female friendship that I haven’t seen on screen before. And it was painfully honest. What inspired you to explore the friend breakup?

Issa: One, we felt like the characters in the last season were building to this point of not being on the same page, and they had fought before. But Prentice [Penny, Insecure’s showrunner], during one of our monthly retreats, came up with that line, where he was like, "Yeah, I just had this vision of starting the season and hearing Issa say, ‘I don’t fuck with Molly anymore.’" And it clicked. It was like, of course.

We don’t really get these stories that are rich and treated with the same sincerity and hurt and anguish that romances are. Friendships are relationships. They are romances; you love your friends. And nobody respects friendship breakups in the same way as you respect a romantic breakup, but they affect your life, and you take them for granted, and there was something so beautiful about examining the little paper cuts, which almost hurt more. That was something that we broke down from the beginning, examining what happens when it’s nobody’s fault.

Elaine: Oh, my God. That! That’s like an R&B lyric for a female friendship breakup song.

Issa: It’s something that I’ve been through, too, where you can’t control where your life goes. I remember one of my most devastating ones was because I didn’t know how to handle a divorce that she was going through. I had never experienced a marriage, and I didn’t know what she needed from me. To her, I might’ve felt flippant about it because I didn’t know how to handle that.

And, for me, I was launching my career, and I felt like she wasn’t there for certain milestones and didn’t understand or respect what I was doing, and that’s not her fault. She was a doctor and she knew a very specific path that wasn’t as forgiving or as thoughtful about the milestones that I felt like I accomplished. And that’s not her fault. So it was neither one of our faults, but it accumulated, and we’ve never been the same since.

Elaine: For somebody who started their whole career on the internet, you’ve managed to successfully keep all your business off the internet for the most part. How do you think about that?

Issa Rae: I’ve always been private even in my friendships, because I’m like, "Oh, people don’t care." I joke that my friend scarred me because I was telling my business in high school, and she was like, "But, Issa, nobody cares. Stop." And then I was like, "Don’t nobody do care. That’s true." That stuck with me. Or even hearing, again, in my friendship circles, people that talk shit about relationships and root for your shit to fail in so many ways. I don’t want to give anybody anything to wish to fail.

I think in the industry, when things are public facing, that is especially true and so many people have things to say. I remember, back in the day, I used to post my relationship from a long time ago. And I remember I saw these commenters that I didn’t know, comment on an old picture and be like, "See." And I was like, "Oh, I don’t like this." And then, from that point forward, I was like, "Oh, I’m never acknowledging anything."

Elaine: What’s so beautiful to me about your work is that you’re able to center stories around everyday Black life, not the oppression or the strife that we experience, not these unrealistic magical Negro tropes. And it’s something to marvel at, to be able to do a show that’s so grounded in normalcy but also really rich and compelling.

Issa: Thank you, I’ll receive it. I think it comes from who’s in the room, too. We’re very intentional about making sure that the room felt like, yes, it’s majority Black, but we don’t all think the same. Our white people get it and are open about what they don’t know and what they do know. And we’re telling a very human experience that is also specifically Black, and that helps. We’re mining real stories, so it feels so good to hear you say that.

Elaine: You’re not just a force on screen and on the page, you are a force as a leader and a boss. I know this because you let me be a fly on the wall of your set this season and it was one of the most diverse sets I’ve ever seen. It was a set where young Black people and women felt empowered. Sadly, that’s not the norm. How do you cultivate that kind of culture as a leader?

Issa: I do think about what environment I want to be a part of. If it weren’t me or if it weren’t my show, would I want to be on this set?

I love to be around diverse people. I love us, but I also like to see us work. I love to see us get opportunities, and I love to see what we do with those opportunities. There’s nothing more refreshing than to hear about where the PAs wanted to go after this and what they wanted to do, and to be able to put them in a position to do that with the experience is so cool to me.

And then to see people who are good at their fucking job is so exciting, and them lending their talents to our show. That shit is incredible.

Elaine: We’ve been having these conversations forever, but now, especially in the wake of Black Lives Matter, there’s this sudden urgency. I’m sure you get the phone calls asking you for advice about how to do what you’ve been doing as far as hiring qualified Black people. Is it annoying when people are now suddenly interested in making that a priority and looking to you to hold their hand and help them figure out the way forward?

Issa: Well, it’s definitely not annoying that they’re making [it] a priority, but it is annoying that it is like, "Well, what should I do?" And it’s like, "Do the fucking work. Just do it, find it." You create worlds out of nothing, but you can’t find a Black PA or a gaffer or whatever? Google, get references. It’s so easy. That’s what I do. They don’t fall in my lap — I seek it.

Since we’ve had these uprisings, since we’ve had these Hollywood conversations, I’ve been on white-ass sets that are acknowledging why we need diversity. So I’m like, "Something’s really clicking." But I don’t know what else to tell you. I can only show you or do it, but I’m not the one. I am tired. I got exhausted having these conversations the other day, where I’m like … I don’t want to be the tokenized person for you to talk about these experiences with. But I’ve said that before, too, and I still am.

Elaine: Do you think anything is going to change?

Issa: Yes, because I see the people doing the work, and I’m part of these conversations. I know that certain companies have empowered the voices that are interested in making a change and that are really about that life. But there’s still some empty gestures that I’m like, "You’ll never get it." It really is going to be up to us. But as long as you’re getting out of the way and truly leaving it up to us, then I do feel OK about it.

Elaine: Last week I got into this really deep conversation about white validation, and whether Black excellence still seeks white validation on some level. Coming off of the Emmys, I’m curious how much those nominations mean to you at this point in your career.

Issa: I think the Emmys feel less like white validation to me, even though I know that they are because of the majority of voters and who gets acknowledged. But I’d like ideally for the Emmys to represent the best in television.

Elaine: As well they should.

Issa: So that’s why it’s an honor to be nominated, because they’ve been held up as the best of television, not necessarily white validation. But yes, they are white-created awards. And so for me the frustration comes more in who’s voting and whose voice is being heard. I think about that more. But I was still happy to get these nominations. You celebrate if you win and then you say, "Oh, this is racist," if you lose. So I’m like, "Which is it?"

So I like to consider it as trying to diversify behind the scenes as much as possible to truly make them what they’re supposed to be. Nobody questions the NBA championship because you’re like, "The best team won." Art is already subjective, so it’s a little bit harder, but I want the Emmys to be like the NBA championship.

Elaine: I think the best part of the Emmys were those interstitials, and particularly your interstitial where you talked about what it was like pitching your show to a white executive who didn’t get it, and had the audacity to tell you what Black people wanted to see, and your reaction to that.

Issa: I felt bad about it after I did it, like I shouldn’t have said it.

Elaine: Wait, why’d you feel bad?

Issa: Because it felt petty. I mean, I knew it was petty, even when I said it, and laughed. It’s a story that I tell usually in private, and so to put it on this platform felt like, "Oh, am I doing the most?" But [that meeting] made me who I am, and yes, it was a motivator of, you can’t let people tell you… That is the prime example of someone who wanted us to seek white validation in a way, under the guise of empowering Black narratives. And that did not sit right with me.

Elaine: I want to take it back, back, back. I want to ask you, growing up, what was your favorite game to play or your favorite toy to play with?

Issa: I used to do this make-believe restaurant with my brother with this stupid toy phone that had you press the button and it had voices. You press the white man, and it’d be like, "Hello, this is Daddy. Pick up the phone." And you pick up. You press the mom button. And for some reason we turned that into this restaurant franchise, like, "Daddy’s calling. Get the burger." It was called Hamburgers Everywhere. There was something about the feeling of owning a restaurant that excited me.

Elaine: You were already a boss as a little kid.

Issa: Bossy.

Elaine: We only talked about [Hollywood], this one part of your life, but you have so many businesses. How do you plot your success when you’re expanding into so many different directions, even in lanes maybe not everyone knows you operate in? You have a music label. You have a coffee shop.

Issa: I think about what I want to do and what I can do, what comes naturally to me, what I still feel excited about talking about at 2:00 a.m. or 3:00 a.m. And I want to work with the competent people that can do it because I know that there’s only so much of me that can make something good. I’m essentially also investing in people.

So with the music label, yes, there’s only so much that I’m going to bring to the table. But the person who runs it is going to have to be making sure that it’s a business, and the artists have to feel represented. So I have to entrust those people to do their jobs. And I do.

With the coffee shop, that is a partnership. It’s something that I’ve always wanted. And it was the right time to do it. I am impulsive. But I don’t hesitate to put something to the side if I feel like I can’t do it justice.

Elaine: You also have a hair brand now that you’re taking on, Sienna Naturals. Congrats!

Issa: That is, again, in partnership with someone [Hannah Diop] who I’ve watched since 2014, who made these products and developed them into what she wanted them to be. I need to be a face of a product that I believe in.

Elaine: Come through, Issa Rae empire. What’s next? World domination? Seriously, what’s the next frontier for you?

Issa: I won’t know until I’m there, but I really have said this from the beginning: Environmental innovation is really, really… the issues are so dire. I don’t know what my role in that is. I am not an engineer. I don’t know what I’m talking about. All I know is what the problem is, but I want to figure out what my role is to save this earth — if it’s meant to be saved, because right now it doesn’t look like it’s meant to be saved. Seems like we’re all supposed to perish.

Elaine: I think we need you to save us. You’ve clearly figured out a lot of other shit. Now, I think maybe you can figure out how to save us.

Top image credit: Kendra Duplantier top; Chanel pants; Gucci necklace; Ben Oni earrings; Third Crown rings; Angela Scott shoes.

Photographer: Micaiah Carter

Stylist: Jason Rembert

Art Director: Erin Hover

Hair: Felicia Leatherwood

Makeup: Joanna Simkin

VP Of Fashion: Tiffany Reid

VP Of Creative: Karen Hibbert

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